Startseite Dicarbonyl compounds in the synthesis of heterocycles under green conditions
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Dicarbonyl compounds in the synthesis of heterocycles under green conditions

  • Daniela Hartwig EMAIL logo , Liane K. Soares , Luiz H. Dapper , José E. R. Nascimento und Eder João Lenardão ORCID logo EMAIL logo
Veröffentlicht/Copyright: 10. Januar 2022
Veröffentlichen auch Sie bei De Gruyter Brill
Manuskript einreichen Informationen für Autor*innen
Physical Sciences Reviews
Aus der Zeitschrift Physical Sciences Reviews Band 8 Heft 9

Abstract

Carbon–carbon and carbon-heteroatom bond forming reactions are strategically employed for the generation of a variety of heterocyclic systems. This class of compounds represents the most general structural unit, present in many natural compounds. They are recognized for their valuable biologically properties and wide range of applications in medicinal, pharmaceutical, and other related fields of chemistry. This is an updated review on the use of dicarbonyl compounds under environmentally friendly conditions to access a series of heterocyclic structures, e.g., quinoxaline, quinazolinones, benzochalcogenazoles, indoles, among others. Synthetic protocols involving copper-catalyzed, multicomponent and cascade reactions, decarboxylative cyclization, recycling of CO2, and electrochemical approaches are presented and discussed.

Keywords: alternative energy sources; alternative solvents; catalysis; dicarbonyl compounds; green synthesis; heterocycles
Corresponding authors: Daniela Hartwig and Eder João Lenardão, Laboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil, E-mail: (D. Hartwig) and (E.J. Lenardão)

Funding source: Conselho Nacional de Desenvolvimento Científico e Tecnológico

Funding source: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

Award Identifier / Grant number: 001

Funding source: Financiadora de Estudos e Projetos

Funding source: Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The study was supported by Conselho Nacional de Desenvolvimento Científico e Tecnológico, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (001), Financiadora de Estudos e Projetos, and Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Sapra, R, Patel, D, Meshram, D. A mini review: recent developments of heterocyclic chemistry in some drug discovery scaffolds synthesis. J Med Chem Sci 2020;3:71–8.Suche in Google Scholar

2. Casar, Z. Synthesis of heterocycles in contemporary medicinal chemistry. In: Maes, B, Cossy, J, Polanc, S, editors. Topics in heterocyclic chemistry. Cham, Switzerland: Springer; 2016.10.1007/978-3-319-39917-1Suche in Google Scholar

3. Griboura, N, Gatzonas, K, Neochoritis, CG. Still relevant today: the asinger multicomponent reaction. ChemMedChem 2021;16:1997–2020. https://doi.org/10.1002/cmdc.202100086.Suche in Google Scholar PubMed

4. Roschangar, F, Sheldon, RA, Senanayake, CH. Overcoming barriers to green chemistry in the pharmaceutical industry - the Green Aspiration LevelTM concept. Green Chem 2015;17:752–68. https://doi.org/10.1039/c4gc01563k.Suche in Google Scholar

5. Dunn, PJ, Wells, AS, Williams, MT. Green chemistry in the pharmaceutical industry. Weinheim, Germany: Wiley-VCH Verlag; 2010.10.1002/9783527629688Suche in Google Scholar

6. Zhang, W, Cue, BW. Green techniques for organic synthesis and medicinal chemistry, 2nd ed. New Delhi: John Wiley & Sons Ltd; 2018.10.1002/9781119288152Suche in Google Scholar

7. Li, CJ. Green processes. In: Anastas, PT, editor. Handbook of green chemistry, vol 7. Weinheim, Germany: Wiley-VCH Verlag; 2012.Suche in Google Scholar

8. Sheldon, RA. Metrics of green chemistry and sustainability: past, present, and future. ACS Sustainable Chem Eng 2018;6:32–48. https://doi.org/10.1021/acssuschemeng.7b03505.Suche in Google Scholar

9. Kaur, N, Grewal, P, Poonia, K. Dicarbonyl compounds in O-heterocycle synthesis. Synth Commun 2021;51:2423–44. https://doi.org/10.1080/00397911.2021.1941114.Suche in Google Scholar

10. Denisov, DA, Novikov, RA, Tomilov, YV. Lewis acid mediated Michael addition of non-aromatic multiple Csingle bondC bonds to α,β-unsaturated dicarbonyl compounds. Tetrahedron Lett 2021;80:153272. https://doi.org/10.1016/j.tetlet.2021.153272.Suche in Google Scholar

11. Byrne, FP, Jin, S, Paggiola, G, Petchey, THM, Clark, JH, Farmer, TJ, et al.. Tools and techniques for solvent selection: green solvent selection guides. Sustain Chem Process 2016;4:7.10.1186/s40508-016-0051-zSuche in Google Scholar

12. Capello, C, Fischer, U, Hungerbühler, K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem 2007;9:927–34. https://doi.org/10.1039/b617536h.Suche in Google Scholar

13. De Marco, BA, Rechelo, BS, Tolóti, EG, Kogawa, AC, Salgado, HRN. Evolution of green chemistry and its multidimensional impacts: a review. Saudi Pharmaceut J 2019;27:1–8. https://doi.org/10.1016/j.jsps.2018.07.011.Suche in Google Scholar PubMed PubMed Central

14. Xu, Z, Yan, P, Jiang, H, Liu, K, Zhang, ZC. Iridium-catalyzed reductive amination of levulinic acid to pyrrolidinones under H2 in water. Chin J Chem 2017;35:581–5. https://doi.org/10.1002/cjoc.201600726.Suche in Google Scholar

15. Wang, S, Huang, H, Bruneau, C, Fischmeister, C. Selective and efficient iridium catalyst for the reductive amination of levulinic acid into pyrrolidones. ChemSusChem 2017;10:4150–4. https://doi.org/10.1002/cssc.201701299.Suche in Google Scholar PubMed

16. Wang, K, Heltzel, J, Sandefur, E, Culley, K, Lemcoff, G, Voutchkova-Kostar, A. Transfer hydrogenation of levulinic acid from glycerol and ethanol using water-soluble iridium N-heterocyclic carbene complexes. J Organomet Chem 2020;919:121310. https://doi.org/10.1016/j.jorganchem.2020.121310.Suche in Google Scholar

17. Hasaninejad, A, Mandegani, F, Beyrati, M, Marymabadi, A, Mohebbi, G. Highly efficient synthesis of spirooxindole, spiroacenaphthylene and bisbenzo[b]pyran derivatives and evaluation of their inhibitory activity against sirtuin 2. ChemistrySelect 2017;2:6784–96. https://doi.org/10.1002/slct.201701364.Suche in Google Scholar

18. Azimzadeh-Saseghi, S, Yavari, I. Choline chloride/pentaerythritol: a deep eutectic solvent for the synthesis of pyran and chromene derivatives. J Iran Chem Soc 2021;18:1261–7.10.1007/s13738-020-02108-5Suche in Google Scholar

19. Sahoo, BM, Banik, BK. Solvent-less reactions: green and sustainable approaches in medicinal chemistry. In: Banik, BK, editor. Advances in green and sustainable chemistry, green approaches in medicinal chemistry for sustainable drug design. Amsterdam, Netherlands: Elsevier; 2020:523–48 pp.10.1016/B978-0-12-817592-7.00014-9Suche in Google Scholar

20. Rao, RN, Jena, S, Mukherjee, M, Maiti, B, Chanda, K. Green synthesis of biologically active heterocycles of medicinal importance: a review. Environ Chem Lett 2021;19:3315–58. https://doi.org/10.1007/s10311-021-01232-9.Suche in Google Scholar

21. Wu, C, Luo, X, Zhang, H, Liu, X, Ji, G, Liu, Z, et al.. Reductive amination/cyclization of levulinic acid to pyrrolidones versus pyrrolidines by switching the catalyst from AlCl3 to RuCl3 under mild conditions. Green Chem 2017;19:3525–9. https://doi.org/10.1039/c7gc00999b.Suche in Google Scholar

22. Wu, C, Zhang, H, Yu, B, Chen, Y, Ke, Z, Guo, S, et al.. Lactate-based ionic liquid catalyzed reductive amination/cyclization of keto acids under mild conditions: a metal-free route to synthesize lactams. ACS Catal 2017;7:7772–6. https://doi.org/10.1021/acscatal.7b02231.Suche in Google Scholar

23. Sharma, MG, Rajani, DP, Patel, HM. Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction. R Soc Open Sci 2017;4:170006. https://doi.org/10.1098/rsos.170006.Suche in Google Scholar PubMed PubMed Central

24. Pachechne, LA, Pereira, VF, Martins, GM, Martendal, E, Xavier, FR, Mendes, SM. One-pot multicomponent synthesis of 1,2,3,4-tetrasubstituted pyrroles catalyzed by [NMPH]CH3SO3. Tetrahedron Lett 2019;60:151043–7. https://doi.org/10.1016/j.tetlet.2019.151043.Suche in Google Scholar

25. Louroubi, A, Nayad, A, Hasnaoui, A, Idouhli, R, Abouelfida, A, Firdoussi, LE, et al.. Natural hydroxyapatite: green catalyst for the synthesis of pyrroles, inhibitors of corrosion. J Chem 2021. https://doi.org/10.1155/2021/6613243.Suche in Google Scholar

26. Mohamadpour, F, Maghsoodlou, MT, Heydari, R, Lashkari, M. Copper(II) acetate monohydrate: an efficient and eco-friendly catalyst for the one-pot multi-component synthesis of biologically active spiropyrans and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions. Res Chem Intermed 2016;42:7841–53. https://doi.org/10.1007/s11164-016-2565-0.Suche in Google Scholar

27. Mohamadpour, F. Carboxymethyl cellulose (CMC) as a recyclable green catalyst promoted eco-friendly protocol for the solvent-free synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Polycycl Aromat Comp 2020. https://doi.org/10.1080/10406638.2020.1768412.Suche in Google Scholar

28. Mohamadpour, F. Theophylline as a green catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Org Prep Proced Int 2020;52:64–8. https://doi.org/10.1080/00304948.2019.1697611.Suche in Google Scholar

29. Mohamadpour, F, Maghsoodlou, MT, Lashkari, M, Heydari, R, Hazeri, N. Synthesis of quinolines, spiro[4H-pyran-oxindoles] and xanthenes under solvent-free conditions. Org Prep Proced Int 2019;51:456–76. https://doi.org/10.1080/00304948.2019.1653126.Suche in Google Scholar

30. Lu, B, Xie, Z, Lu, J, Liu, J, Cui, S, Ma, Y, et al.. Highly atom-economic, catalyst-free, and solvent-free synthesis of phthalazinones. ACS Sustainable Chem Eng 2019;7:134–8. https://doi.org/10.1021/acssuschemeng.8b05657.Suche in Google Scholar

31. Gupta, S, Khurana, JM. An efficient approach for the synthesis of 5-hydroxy-chromeno[2,3-b]pyridines under catalyst and solvent free conditions. Green Chem 2017;19:4153–6. https://doi.org/10.1039/c7gc01463e.Suche in Google Scholar

32. Kim, Y, Li, C-J. Perspectives on green synthesis and catalysis. Green Synth Catal 2020;1:1–11. https://doi.org/10.1016/j.gresc.2020.06.002.Suche in Google Scholar

33. Sheldon, RA, Arends, IWCE, Hanefeld, U. Green chemistry and catalysis. Weinheim, Germany: Wiley-VCH; 2007.10.1002/9783527611003Suche in Google Scholar

34. Gajengi, AL, Fernandes, CS, Bhanage, BM. Synthesis of Cu2O/Ag nanocomposite and their catalytic application for the one pot synthesis of substituted pyrroles. Mol Catal 2018;451:13–9. https://doi.org/10.1016/j.mcat.2017.10.010.Suche in Google Scholar

35. Alishahi, N, Mohammadpoor-Baltork, I, Tangestaninejad, S, Mirkhani, V, Moghadam, M, Kia, R. Calixarene based ionic liquid as an efficient and reusable catalyst for one-pot multicomponent synthesis of polysubstituted pyridines and bis-pyridines. ChemistrySelect 2019;4:5903–10. https://doi.org/10.1002/slct.201900902.Suche in Google Scholar

36. Tayade, YA, Dalal, DS. β-Cyclodextrin as a supramolecular catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives in water. Catal Lett 2017;147:1411–21. https://doi.org/10.1007/s10562-017-2032-6.Suche in Google Scholar

37. Yazdani-Elah-Abadi, A, Razeghi, M, Shams, N, Kangani, M, Mohebat, R. Fulvic acid: an efficient and green catalyst for the one-pot four-component domino synthesis of benzo[a]phenazine annulated heterocycles in aqueous medium. Org Prep Proced Int 2020;52:48–55. https://doi.org/10.1080/00304948.2019.1697608.Suche in Google Scholar

38. Panshina, SY, Ponomarenkoc, OV, Bakibaeva, AA, Malkova, VS. New synthesis of 2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione using etidronic acid as a “green” catalyst. Russ J Org Chem 2020;56:2067–73. https://doi.org/10.1134/s1070428020120039.Suche in Google Scholar

39. Javanshir, S, Pourshiri, NS, Dolatkhah, Z, Farhadnia, M. Caspian Isinglass, a versatile and sustainable biocatalyst for domino synthesis of spirooxindoles and spiroacenaphthylenes in water. Monatsh Chem 2017;148:703–10. https://doi.org/10.1007/s00706-016-1779-6.Suche in Google Scholar

40. Willis, NJ, Fisher, CA, Alder, CM, Harsanyi, A, Shukla, L, Adams, JP, et al.. Sustainable synthesis of enantiopure fluorolactam derivatives by a selective direct fluorination - amidase strategy. Green Chem 2016;18:1313–8. https://doi.org/10.1039/c5gc02209f.Suche in Google Scholar

41. Maleki, A, Azizi, M, Emdadi, Z. A novel poly(ethyleneoxide)-based magnetic nanocomposite catalyst for highly efficient multicomponent synthesis of pyran derivatives. Green Chem Lett Rev 2018;11:573–82. https://doi.org/10.1080/17518253.2018.1547795.Suche in Google Scholar

42. Maleki, A, Azadegan, S. Preparation and characterization of silica-supported magnetic nanocatalyst and application in the synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives. Inorg Nano-Met Chem 2017;47:917–24. https://doi.org/10.1080/24701556.2016.1241266.Suche in Google Scholar

43. Asadi, B, Landarani-Isfahani, A, Mohammadpoor-Baltork, I, Tangestaninejad, S, Moghadam, M, Mirkhani, V, et al.. Diastereoselective synthesis of symmetrical and unsymmetrical tetrahydropyridines catalyzed by Bi(III) immobilized on triazine dendrimer stabilized magnetic nanoparticles. ACS Comb Sci 2017;19:356–64. https://doi.org/10.1021/acscombsci.6b00180.Suche in Google Scholar PubMed

44. Babaei, E, Mirjalili, BBF. One-pot synthesis of five substituted tetrahydropyridines using nano-Al2O3/BF3/Fe3O4 as a highly efficient nano-catalyst. Res Chem Intermed 2018;44:3493–505. https://doi.org/10.1007/s11164-018-3320-5.Suche in Google Scholar

45. Abadi, AYE, Maghsoodlou, M-T, Heydari, R, Mohebat, R. An efficient four-component domino protocol for the rapid and green synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives using caffeine as a homogeneous catalyst. Res Chem Intermed 2016;42:1227–35. https://doi.org/10.1007/s11164-015-2083-5.Suche in Google Scholar

46. Debnath, K, Mukherjee, S, Bodhak, C, Pramanik, A. Facile one-pot three-component synthesis of diverse 2,3- disubstituted isoindolin-1-ones using ZrO2 nanoparticles as a reusable dual acid-base solid support under solvent-free conditions. RSC Adv 2016;6:21127–38. https://doi.org/10.1039/c6ra00870d.Suche in Google Scholar

47. Amirmahani, N, Mahmoodi, NO, Malakootian, M, Pardakhty, A. [TBP]2SO4 ionic liquid catalyst for 4MCR of pyridazinoindazole, indazolophthalazine and pyrazolophthalazine derivatives. Mol Divers 2020. https://doi.org/10.1007/s11030-020-10153-8.Suche in Google Scholar PubMed

48. Kurniawan, YS, Priyangga, KTA, Krisbiantoro, PA, Imawan, AC. Green chemistry influences in organic synthesis: a review. J Multidiscip Appl Nat Sci 2021;1:1–12. https://doi.org/10.47352/jmans.v1i1.2.Suche in Google Scholar

49. Anastas, PT, Warner, J. Green chemistry: theory and practice. Oxford: Oxford University Press; 1998.Suche in Google Scholar

50. Fechete, J, Jacques, Y, Védrine, C. The past, present and future of heterogeneous catalysis. Catal Today 2012;189:2–27. https://doi.org/10.1016/j.cattod.2012.04.003.Suche in Google Scholar

51. Védrine, JC. Heterogeneous catalysis on metal oxides. Catalysts 2017;7:341–66. https://doi.org/10.3390/catal7110341.Suche in Google Scholar

52. Gajengi, AL, Bhanage, BM. NiO nanoparticles: efficient catalyst for four component coupling reaction for synthesis of substituted pyrroles. Catal Lett 2016;146:1341–7. https://doi.org/10.1007/s10562-016-1762-1.Suche in Google Scholar

53. Zhang, J, Xie, B, Wang, L, Yi, X, Wang, C, Wang, G, et al.. Zirconium oxide supported palladium nanoparticles as a highly efficient catalyst in the hydrogenation-amination of levulinic acid to pyrrolidones. ChemCatChem 2016;9:2661–7. https://doi.org/10.1002/cctc.201600739.Suche in Google Scholar

54. Jafarpour, M, Rezaeifard, A. A zirconium Schiff base complex immobilized on starch-coated maghemite nanoparticles catalyzes heterogeneous condensation of 1,2-diamines with 1,2-dicarbonyl compounds. Transit Met Chem 2016;41:205–11. https://doi.org/10.1007/s11243-015-0012-5.Suche in Google Scholar

55. Naeimi, H, Dida, A. Facile one-pot four component synthesis of pyrido[2,3-d:6,5-d′]dipyrimidines catalyzed by CuFe2O4 magnetic nanoparticles in water. J Mol Struct 2017;1137:626–33. https://doi.org/10.1016/j.molstruc.2017.02.044.Suche in Google Scholar

56. Maleki, A, Ghassemi, M, Firouzi-Haji, R. Green multicomponent synthesis of four different classes of six-membered N-containing and O-containing heterocycles catalyzed by an efficient chitosan-based magnetic bionanocomposite. Pure Appl Chem 2018;90:387–94. https://doi.org/10.1515/pac-2017-0702.Suche in Google Scholar

57. Patil, S, Mane, A, Dhongade-Desai, S. Cuo nanoparticles as a reusable catalyst for the synthesis of 1Hpyrazolo[1,2-b]phthalazine-5,10-dione derivates under solvent-free conditions. J Iran Chem Soc 2019;16:1665–75. https://doi.org/10.1007/s13738-019-01640-3.Suche in Google Scholar

58. Xie, C, Song, J, Wu, H, Hu, Y, Liu, H, Zhang, Z, et al.. Ambient reductive amination of levulinic acid to pyrrolidones over Pt Nanocatalysts on porous TiO2 nanosheets. J Am Chem Soc 2019;141:4002–9. https://doi.org/10.1021/jacs.8b13024.Suche in Google Scholar PubMed

59. Buckley, BR. Organocatalysis. Annu Rep Prog Chem Sect B Org Chem 2013;109:189–206. https://doi.org/10.1039/c3oc90015k.Suche in Google Scholar

60. Antenucci, A, Dughera, S, Renzi, P. Green chemistry meets asymmetric organocatalysis: a critical overview on catalysts synthesis. ChemSusChem 2021;14:2785–853. https://doi.org/10.1002/cssc.202100573.Suche in Google Scholar PubMed PubMed Central

61. Roymahapatra, G, Adak, AK, Samanta, T, Khatua, PK, Jana, RN. Approach of organocatalysis techniques towards “green chemistry”. Int J Innov Pract Appl Res 2016;5:131–42.Suche in Google Scholar

62. Mohebat, R, Yazdani, A, Abadi, E, Maghsoodlou, MT, Mohammadi, M, Heydari, R. A green and efficient four-component sequential protocol for the synthesis of novel 16-(aryl)benzo[a]indeno[20,10:5,6]pyrano[2,3c]phenazin-15(16H)-one derivatives using oxalic acid as a reusable and cost-effective organic catalyst. Res Chem Intermed 2016;9:7121–32. https://doi.org/10.1007/s11164-016-2522-y.Suche in Google Scholar

63. Gupta, S, Saluja, P, Khurana, JM. DBU mediated confluent approach for the one pot synthesis of novel 5-hydroxy pyrazolo[1,2-a][1,2,4. triazoles and their dehydration to novel pyrazolo[1,2-a][1,2,4]triazole derivatives. Tetrahedron 2016;72:3986–93. https://doi.org/10.1016/j.tet.2016.05.021.Suche in Google Scholar

64. Kumari, S, Singh, H, Khurana, JM. An efficient green approach for the synthesis of novel triazolyl spirocyclic oxindole derivatives via one-pot five component protocol using DBU as catalyst in PEG-400. Tetrahedron Lett 2016;57:3081–5. https://doi.org/10.1016/j.tetlet.2016.05.084.Suche in Google Scholar

65. Hassani, M, Mohammad, R, Jamal, N, Panahi, L. One-pot multicomponent synthesis of substituted pyrroles by using chitosan as an organocatalyst. ChemistrySelect 2018;3:666–72. https://doi.org/10.1002/slct.201702692.Suche in Google Scholar

66. Fallah-Mehrjardi, M, Shirzadi, M, Banitaba, SH. A new basic ionic liquid supported on magnetite nanoparticles: an efficient phase-transfer catalyst for the green synthesis of 2-amino-3-cyano-4Hpyrans. Polycycl Aromat Comp 2020. https://doi.org/10.1080/10406638.2020.1830131.Suche in Google Scholar

67. Gawande, MB, Bonifácio, VDB, Luque, R, Branco, PS, Varma, RS. Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis. Chem Soc Rev 2013;42:5522–52. https://doi.org/10.1039/c3cs60025d.Suche in Google Scholar PubMed

68. Abdussalam-Mohammeda, W, Alia, AQ, Errayesb, AO. Green chemistry: principles, applications, and disadvantages. Chem Methodol 2020;4:408–23.10.33945/SAMI/CHEMM.2020.4.4Suche in Google Scholar

69. Saroha, M, Khanna, G, Khurana, JM. Synthesis of novel 5-substituted 6-phenylpyrrolo[2,3-d] pyrimidine derivatives via one-pot three-component reactions under catalyst-free condition. ChemistrySelect 2017;2:7263–6. https://doi.org/10.1002/slct.201701234.Suche in Google Scholar

70. Kong, D, Lu, G, Wu, M, Shi, Z, Lin, Q. One-Pot, catalyst-free synthesis of spiro[dihydroquinolinenaphthofuranone] compounds from isatins in water triggered by hydrogen bonding effects. ACS Sustainable Chem Eng 2017;5:3465–70. https://doi.org/10.1021/acssuschemeng.7b00145.Suche in Google Scholar

71. Brahmachari, G, Nurjamal, K, Karmakar, I, Begam, S, Nayek, N, Mandal, B. Development of a water-mediated and catalyst-free green protocol for easy access to a huge array of diverse and densely functionalized pyrido[2,3-d:6,5-d′]dipyrimidines via one-pot multicomponent reaction under ambient conditions. ACS Sustainable Chem Eng 2017;5:9494–505. https://doi.org/10.1021/acssuschemeng.7b02696.Suche in Google Scholar

72. Brahmachari, G, Nayek, N. Catalyst-free one-pot three-component synthesis of diversely substituted 5-aryl-2-oxo-/thioxo-2,3dihydro-1H-benzo[6,7]chromeno[2,3-d]pyrimidine-4,6,11(5H)-triones under ambient conditions. ACS Omega 2017;2:5025–35. https://doi.org/10.1021/acsomega.7b00791.Suche in Google Scholar PubMed PubMed Central

73. Meena, K, Saroha, M, Khurana, I, Malik, A, Rai, PK, Khurana, JM. Catalyst-free one-pot regioselective synthesis of benzo[d]imidazo[2,1-b]thiazoles by heating or grinding. J Heterocycl Chem 2019;56:3055–64.10.1002/jhet.3702Suche in Google Scholar

74. Cao, TT, Zhang, WK, Qin, FH, Kagn, QQ, Dong, Y, Li, Q, et al.. Halocyclization of olefinic 1,3-dicarbonyls and olefinic amides in aqueous media open in air at room temperature. ACS Sustainable Chem Eng 2020;8:16946–51. https://doi.org/10.1021/acssuschemeng.0c06586.Suche in Google Scholar

75. Zhao, W, Meier, S, Yang, S, Riisager, A. Insights into ammonia borane-enabled green synthesis of N-Substituted lactams from biomass-derived keto acids and amines. ACS Sustainable Chem Eng 2021;9:4377–82. https://doi.org/10.1021/acssuschemeng.1c00211.Suche in Google Scholar

76. Jiang, XQ, Chen, SQ, Liu, YF, Pan, XG, Chen, D, Wang, SF. Solvothermal synthesis of multiple dihydropyrimidinones at a time as inhibitors of Eg5. Molecules 2021;26:1925. https://doi.org/10.3390/molecules26071925.Suche in Google Scholar PubMed PubMed Central

77. Elumalai, V, Hansen, JH. A green, scalable, and catalyst-free one-minute synthesis of quinoxalines. SynOpen 2021;5:43–8.10.1055/s-0040-1706021Suche in Google Scholar

78. Narayanam, JMR, Stephenson, CRJ. Visible light photoredox catalysis: applications in organic synthesis. Chem Soc Rev 2011;40:102–13. https://doi.org/10.1039/b913880n.Suche in Google Scholar PubMed

79. Chen, J-R, Hu, X-Q, Lu, L-Q, Xiao, W-J. Visible light photoredox-controlled reactions of N-radicals and radical ions. Chem Soc Rev 2016;45:2044–56. https://doi.org/10.1039/c5cs00655d.Suche in Google Scholar PubMed

80. Lang, X, Zhao, J, Chen, X. Cooperative photoredox catalysis. Chem Soc Rev 2016;45:3026–38. https://doi.org/10.1039/c5cs00659g.Suche in Google Scholar PubMed

81. Dutta, A, Rahman, N, Kumar, JE, Rabha, J, Phukan, T, Nongkhlaw, R. Catalyst-free UV365-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities. Synth Commun 2021;51:263–78. https://doi.org/10.1080/00397911.2020.1825741.Suche in Google Scholar

82. Tiwari, J, Saquib, M, Singh, S, Tufail, F, Singh, M, Singh, J, et al.. Visible light promoted synthesis of dihydropyrano[2,3-c]chromenes via a multicomponent-tandem strategy under solvent and catalyst free conditions. Green Chem 2016;18:3221–31. https://doi.org/10.1039/c5gc02855h.Suche in Google Scholar

83. Kong, H, Li, Q, Yin, Y, Huang, M, Kim, JK, Zhu, Y, et al.. An efficient light on-off one-pot method for the synthesis of 3-styryl coumarins from aryl alkynoates. Org Biomol Chem 2019;17:4621–8. https://doi.org/10.1039/c9ob00421a.Suche in Google Scholar PubMed

84. Nongthombam, GS, Kharmawlong, GK, Kumar, JE, Nongkhlaw, R. UV365 light promoted catalyst-free synthesis of pyrimido[4,5-b]quinoline-2,4-diones in aqueous-glycerol médium. New J Chem 2018;42:9436–42. https://doi.org/10.1039/c8nj01459k.Suche in Google Scholar

85. Zhang, M, Chen, M-N, LiLiu, J-MN, Zhang, Z-H. Visible-light-initiated one-pot, three-component synthesis of 2-amino-4H-pyran-3,5-dicarbonitrile derivatives. ACS Comb Sci 2019;21:685–91. https://doi.org/10.1021/acscombsci.9b00124.Suche in Google Scholar PubMed

86. Mohamadpour, F. Catalyst-free, visible light irradiation promoted synthesis of spiroacenaphthylenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in aqueous ethyl lactate. J Photochem Photobiol, A 2021;18:113041. https://doi.org/10.1016/j.jphotochem.2020.113041.Suche in Google Scholar

87. Shaikh, MA, Farooqui, M, Abed, S. [Bu3NH][HSO4] Catalyzed: an eco-efficient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions. Res Chem Intermed 2018;44:5483–500. https://doi.org/10.1007/s11164-018-3435-8.Suche in Google Scholar

88. Draye, M, Chatel, G, Duwald, R. Ultrasound for drug synthesis: a green approach. Pharmaceuticals 2020;13:23. https://doi.org/10.3390/ph13020023.Suche in Google Scholar PubMed PubMed Central

89. Yao, Y, Pan, Y, Liu, S. Power ultrasound and its applications: a state-of-the-art review. Ultrason Sonochem 2020;62:1047222. https://doi.org/10.1016/j.ultsonch.2019.104722.Suche in Google Scholar PubMed

90. Mohamed, MA. Sonochemistry (applications of ultrasound in chemical synthesis and reactions): a review part I. Az J Pharm Sci 2016;53:117–34. https://doi.org/10.21608/ajps.2016.6890.Suche in Google Scholar

91. Mohamed, MA. Sonochemistry (applications of ultrasound in chemical synthesis and reactions): a review part III. J Pharm Res Int 2019;31:1–19. https://doi.org/10.9734/jpri/2019/v31i630363.Suche in Google Scholar

92. Banerjee, B. Recent developments on ultrasound assisted catalyst-free organic synthesis. Ultrason Sonochem 2017;35:1–14. https://doi.org/10.1016/j.ultsonch.2016.09.023.Suche in Google Scholar PubMed

93. Brahmachari, G, Karmakar, I, Nurjamal, K. Ultrasound-assisted expedient and green synthesis of a new series of diversely functionalized 7-aryl/heteroarylchromeno[4,3-d]pyrido[1,2-a]pyrimidin-6(7H)-ones via one-pot multicomponent reaction under sulfamic acid catalysis at ambient conditions. ACS Sustainable Chem Eng 2018;6:11018–28. https://doi.org/10.1021/acssuschemeng.8b02448.Suche in Google Scholar

94. Costa, GP, Seus, N, Roehrs, JA, Jacob, RG, Schumacher, RF, Barcellos, T, et al.. Ultrasound-promoted organocatalytic enamine-azide [3 + 2] cycloaddition reactions for the synthesis of [(arylselanyl)phenyl-1H-1,2,3-triazol-4-yl]ketones. Beilstein J Org Chem 2017;13:694–702. https://doi.org/10.3762/bjoc.13.68.Suche in Google Scholar PubMed PubMed Central

95. Xavier, DM, Goldani, BS, Seus, N, Jacob, RG, Barcellos, T, Paixão, MW, et al.. Sonochemistry in organocatalytic enamine-azide [3+2] cycloadditions: a rapid alternative for the synthesis of 1,2,3-triazoyl carboxamides. Ultrason Sonochem 2017;34:107–14. https://doi.org/10.1016/j.ultsonch.2016.05.007.Suche in Google Scholar PubMed

96. Penteado, F, Vieira, MM, Perin, G, Alves, D, Jacob, RG, Santi, C, et al.. Niobium-promoted reaction of α-phenylglyoxylic acid with orthofunctionalized anilines: synthesis of 2-arylbenzothiazoles and 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones. Green Chem 2016;18:6675–80. https://doi.org/10.1039/c6gc02495e.Suche in Google Scholar

97. Nongrum, R, Kharmawlong, GK, Rani, JWS, Rahman, N, Dutta, A, Rishanlang Nongkhlaw, R. Organocatalytic green approach towards the fabrication of fused benzo N,N-containing heterocycles facilitated by ultrasonic irradiation. J Heterocycl Chem 2019;56:2873–83.10.1002/jhet.3680Suche in Google Scholar

98. Henary, M, Kananda, C, Rotolo, L, Savino, B, Owens, EA, Cravotto, G. Benefits and applications of microwave-assisted synthesis of nitrogen containing heterocycles in medicinal chemistry. RSC Adv 2020;10:14170–97. https://doi.org/10.1039/d0ra01378a.Suche in Google Scholar PubMed PubMed Central

99. Kamanna, K, Khatavi, SY. Microwave-accelerated carbon-carbon and carbon-heteroatom bond formation via multi-component reactions: a brief overview. Curr Microw Chem 2020;7:23–39. https://doi.org/10.2174/2213346107666200218124147.Suche in Google Scholar

100. Gopi, C, Krupamai, G, Dhanaraju, MD. A recent progress in microwave-assisted synthesis of heterocyclic compounds containing nitrogen, sulphur and oxygen. Rev J Chem 2019;9:255–89. https://doi.org/10.1134/s2079978019040034.Suche in Google Scholar

101. Pal, R, Mukhopadhyay, C. Microwave-assisted carbon-carbon and carbon-heteroatom cross-coupling reactions in organic synthesis. Curr Microw Chem 2020;7:86–98. https://doi.org/10.2174/2213335607666200310121337.Suche in Google Scholar

102. Greñu, BD, Torres, J, García-González, J, Muñoz-Pina, S, Reyes, R, Costero, AM, et al.. Microwave-assisted synthesis of covalent organic frameworks: a review. ChemSusChem 2021;14:208–33. https://doi.org/10.1002/cssc.202001865.Suche in Google Scholar PubMed

103. Kuraitheerthakumaran, A, Pazhamalai, S, Gopalakrishnan, M. Microwave-assisted multicomponent reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)-thiones using lanthanum oxide as a catalyst under solvent-free conditions. Arab J Chem 2016;9:S461–5. https://doi.org/10.1016/j.arabjc.2011.06.005.Suche in Google Scholar

104. Naeimi, H, Didar, A, Rashid, Z. Microwave-assisted synthesis of pyrido-dipyrimidines using magnetically CuFe2O4 nanoparticles as an efficient, reusable, and powerful catalyst in water. J Iran Chem Soc 2016;14:377–85. https://doi.org/10.1007/s13738-016-0986-8.Suche in Google Scholar

105. Ma, X, Zhang, X, Awad, JM, Xie, G, Qiu, W, Zhang, W. One-pot synthesis of tetrahydro-pyrrolobenzodiazepines and tetrahydro-pyrrolobenzodiazepinones through sequential 1,3-dipolar cycloaddition/N-alkylation (N-acylation)/Staudinger/aza-Wittig reactions. Green Chem 2019;21:4489–94. https://doi.org/10.1039/c9gc01642b.Suche in Google Scholar

106. Novaes, LFT, Liu, J, Shen, Y, Lu, L, Meinhardt, JM, Lin, S. Electrocatalysis as an enabling technology for organic synthesis. Chem Soc Rev 2021;50:7941–8002. https://doi.org/10.1039/d1cs00223f.Suche in Google Scholar PubMed PubMed Central

107. Yoshida, J-I, Shimizu, A, Hayashi, R. Electrogenerated cationic reactive intermediates: the pool method and further advances. Chem Rev 2018;118:4702–30. https://doi.org/10.1021/acs.chemrev.7b00475.Suche in Google Scholar PubMed

108. Yan, M, Kuwamata, Y, Baran, PS. Synthetic organic electrochemical methods since 2000: on the verge of a renaissance. Chem Rev 2017;117:13230–319. https://doi.org/10.1021/acs.chemrev.7b00397.Suche in Google Scholar PubMed PubMed Central

109. Guan, Z, Wang, Y, Wang, H, Huang, Y, Wang, S, Tang, H, et al.. Electrochemical oxidative cyclization of olefinic carbonyls with diselenides. Green Chem 2019;21:4976–80. https://doi.org/10.1039/c9gc02665g.Suche in Google Scholar

110. Kong, Y, Li, Y, Huang, M, Kim, JK, Wu, Y. An electrochemical off-on method for pyrimidin-2(1H)-one synthesis via three-component cyclization. Green Chem 2019;21:4495–8. https://doi.org/10.1039/c9gc02005e.Suche in Google Scholar
Published Online: 2022-01-10

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Artikel in diesem Heft

  1. Frontmatter
  2. Reviews
  3. Magnetic characterization of magnetoactive elastomers containing magnetic hard particles using first-order reversal curve analysis
  4. Microscopic understanding of particle-matrix interaction in magnetic hybrid materials by element-specific spectroscopy
  5. Biodeinking: an eco-friendly alternative for chemicals based recycled fiber processing
  6. Bio-based polyurethane aqueous dispersions
  7. Cellulose-based polymers
  8. Biodegradable shape-memory polymers and composites
  9. Natural substances in cancer—do they work?
  10. Personalized and targeted therapies
  11. Identification of potential histone deacetylase inhibitory biflavonoids from Garcinia kola (Guttiferae) using in silico protein-ligand interaction
  12. Chemical computational approaches for optimization of effective surfactants in enhanced oil recovery
  13. Social media and learning in an era of coronavirus among chemistry students in tertiary institutions in Rivers State
  14. Techniques for the detection and quantification of emerging contaminants
  15. Occurrence, fate, and toxicity of emerging contaminants in a diverse ecosystem
  16. Updates on the versatile quinoline heterocycles as anticancer agents
  17. Trends in microbial degradation and bioremediation of emerging contaminants
  18. Power to the city: Assessing the rooftop solar photovoltaic potential in multiple cities of Ecuador
  19. Phytoremediation as an effective tool to handle emerging contaminants
  20. Recent advances and prospects for industrial waste management and product recovery for environmental appliances: a review
  21. Integrating multi-objective superstructure optimization and multi-criteria assessment: a novel methodology for sustainable process design
  22. A conversation on the quartic equation of the secular determinant of methylenecyclopropene
  23. Recent developments in the synthesis and anti-cancer activity of acridine and xanthine-based molecules
  24. An overview of in silico methods used in the design of VEGFR-2 inhibitors as anticancer agents
  25. Fragment based drug design
  26. Advances in heterocycles as DNA intercalating cancer drugs
  27. Systems biology–the transformative approach to integrate sciences across disciplines
  28. Pharmaceutical interest of in-silico approaches
  29. Membrane technologies for sports supplementation
  30. Fused pyrrolo-pyridines and pyrrolo-(iso)quinoline as anticancer agents
  31. Membrane applications in the food industry
  32. Membrane techniques in the production of beverages
  33. Statistical methods for in silico tools used for risk assessment and toxicology
  34. Dicarbonyl compounds in the synthesis of heterocycles under green conditions
  35. Green synthesis of triazolo-nucleoside conjugates via azide–alkyne C–N bond formation
  36. Anaerobic digestion fundamentals, challenges, and technological advances
  37. Survival is the driver for adaptation: safety engineering changed the future, security engineering prevented disasters and transition engineering navigates the pathway to the climate-safe future
https://doi.org/10.1515/psr-2021-0095
Schlagwörter für diesen Artikel
alternative energy sources; alternative solvents; catalysis; dicarbonyl compounds; green synthesis; heterocycles

Artikel in diesem Heft

  1. Frontmatter
  2. Reviews
  3. Magnetic characterization of magnetoactive elastomers containing magnetic hard particles using first-order reversal curve analysis
  4. Microscopic understanding of particle-matrix interaction in magnetic hybrid materials by element-specific spectroscopy
  5. Biodeinking: an eco-friendly alternative for chemicals based recycled fiber processing
  6. Bio-based polyurethane aqueous dispersions
  7. Cellulose-based polymers
  8. Biodegradable shape-memory polymers and composites
  9. Natural substances in cancer—do they work?
  10. Personalized and targeted therapies
  11. Identification of potential histone deacetylase inhibitory biflavonoids from Garcinia kola (Guttiferae) using in silico protein-ligand interaction
  12. Chemical computational approaches for optimization of effective surfactants in enhanced oil recovery
  13. Social media and learning in an era of coronavirus among chemistry students in tertiary institutions in Rivers State
  14. Techniques for the detection and quantification of emerging contaminants
  15. Occurrence, fate, and toxicity of emerging contaminants in a diverse ecosystem
  16. Updates on the versatile quinoline heterocycles as anticancer agents
  17. Trends in microbial degradation and bioremediation of emerging contaminants
  18. Power to the city: Assessing the rooftop solar photovoltaic potential in multiple cities of Ecuador
  19. Phytoremediation as an effective tool to handle emerging contaminants
  20. Recent advances and prospects for industrial waste management and product recovery for environmental appliances: a review
  21. Integrating multi-objective superstructure optimization and multi-criteria assessment: a novel methodology for sustainable process design
  22. A conversation on the quartic equation of the secular determinant of methylenecyclopropene
  23. Recent developments in the synthesis and anti-cancer activity of acridine and xanthine-based molecules
  24. An overview of in silico methods used in the design of VEGFR-2 inhibitors as anticancer agents
  25. Fragment based drug design
  26. Advances in heterocycles as DNA intercalating cancer drugs
  27. Systems biology–the transformative approach to integrate sciences across disciplines
  28. Pharmaceutical interest of in-silico approaches
  29. Membrane technologies for sports supplementation
  30. Fused pyrrolo-pyridines and pyrrolo-(iso)quinoline as anticancer agents
  31. Membrane applications in the food industry
  32. Membrane techniques in the production of beverages
  33. Statistical methods for in silico tools used for risk assessment and toxicology
  34. Dicarbonyl compounds in the synthesis of heterocycles under green conditions
  35. Green synthesis of triazolo-nucleoside conjugates via azide–alkyne C–N bond formation
  36. Anaerobic digestion fundamentals, challenges, and technological advances
  37. Survival is the driver for adaptation: safety engineering changed the future, security engineering prevented disasters and transition engineering navigates the pathway to the climate-safe future
Jetzt anmelden und 20% sparen
Institutioneller Zugang
Wie funktioniert Authentifizierung?
Haben Sie eine Idee, wie wir unsere Website verbessern können?
Bitte schreiben Sie uns.
© 2025 De Gruyter Brill
Heruntergeladen am 21.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/psr-2021-0095/html?lang=de
Button zum nach oben scrollen