Abstract
Of late, regio-selective tandem reactions are given much attention due to the formation of several multiple bonds in a single synthetic operation, avoids altering the reaction conditions, isolation of the intermediates during the reaction, reduces the production of toxic waste to the environment and can produce highly complex organic molecules with desired selectivity. Though, it requires the well-built knowledge for optimization of the process, it permits to make the complex organic molecules with least number of steps, and it has eventually made great interest and inspiration to the upcoming organic chemists. Presentation of current book chapter presents the Cu-Catalysed tandem reactions for building poly hetero atom heterocyclic compounds via green approach.
Funding source: VIT Seed Grant
Award Identifier / Grant number: SG20210267
Acknowledgments
The authors are grateful to VIT, Vellore, Tamil Nadu, India, for granting the ’VIT SEED GRANT-SG20210’ that enabled us to complete this book chapter work. Jyothylakshmi expresses her gratitude to the VIT for providing her a fellowship.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: None declared.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1(a). Nebra, N, García‐Álvarez, J. Catalyzed organic reactions in aqueous media. Copp Catal Org Synth 2020:73–102. https://doi.org/10.1002/9783527826445.ch5.Search in Google Scholar
(b) Barrera-Adame, DA, Álvarez-Caballero, JM, Coy-Barrera, ED. Tandem reactions in organic synthesis: the artistic approach in modern organic chemistry. Revista Facultad de Ciencias Básicas 2016;8:292–309.Search in Google Scholar
2(a). Bruggink, A, Schoevaart, R, Kieboom, T. Concepts of nature in organic synthesis: cascade catalysis and multistep conversions in concert. Org Process Res Dev 2003;7:622–40. https://doi.org/10.1021/op0340311.Search in Google Scholar
(b) Jeyakumar, K, Chand, DK. Copper perchlorate: efficient acetylation catalyst under solvent free conditions. J Mol Catal Chem 2006;255:275–82. https://doi.org/10.1016/j.molcata.2006.04.026.Search in Google Scholar
3. Sheldon, RAE. factors, green chemistry and catalysis: an odyssey. Chem Commun 2008;29:3352–65. https://doi.org/10.1039/b803584a.Search in Google Scholar PubMed
4(a). Grigg, R, Loganathan, V, Sridharan, V, Stevenson, P, Sukirthalingam, S, Worakun, T. Palladium catalysed tandem cyclisation-anion capture processes. Part 2. Cyclisation onto alkynes or allenes with hydride capture. Tetrahedron 1996;52:11479–502. https://doi.org/10.1016/0040-4020(96)00638-2.Search in Google Scholar
(b) Dyker, G. Amino acid derivatives by multicomponent reactions. Angew Chem Int Ed Engl 1997;36:1700–2. https://doi.org/10.1002/anie.199717001.Search in Google Scholar
5. Lu, L-Q, Chen, J-R, Xiao, W-J. Development of cascade reactions for the concise construction of diverse heterocyclic architectures. Acc Chem Res 2012;45:1278–93. https://doi.org/10.1021/ar200338s.Search in Google Scholar PubMed
6. Liu, Y, Wan, JP. Tandem reactions initiated by copper-catalyzed cross-coupling: a new strategy towards heterocycle synthesis. Org Biomol Chem 2011;9:6873–94. https://doi.org/10.1039/c1ob05769c.Search in Google Scholar PubMed
7. Kirsch, SF, Binder, JT, Crone, B, Duschek, A, Haug, TT, Liebert, C, et al.. Catalyzed tandem reaction of 3‐silyloxy‐1, 5‐enynes consisting of cyclization and pinacol rearrangement. Angew Chem Int Ed 2007;46:2310–3. https://doi.org/10.1002/anie.200604544.Search in Google Scholar PubMed
8. Bunce, RA. Recent advances in the use of tandem reactions for organic synthesis. Tetrahedron 1995;51:13103–59. https://doi.org/10.1016/0040-4020(95)00649-s.Search in Google Scholar
9(a). Padwa, A. Tandem methodology for heterocyclic synthesis. Pure Appl Chem 2004;76:1933–52. https://doi.org/10.1351/pac200476111933.Search in Google Scholar
(b) Peters, M. N-Heterocyclic carbene-phosphinidene and carbene-phosphinidenide transition metal complexes. Inorg Chem 2017;56:10785–93. https://doi.org/10.1021/acs.inorgchem.7b01798.Search in Google Scholar PubMed
(c) Doddi, A. N-heterocyclic carbene-phosphinidene complexes of the coinage metals. Chem Eur J 2015;21:16178–89. https://doi.org/10.1002/chem.201502208.Search in Google Scholar PubMed
10(a). Doddi, A, Peters, M, Tamm, M. N-Heterocyclic carbene adducts of main group elements and their use as ligands in transition metal chemistry. Chem Rev 2019;119:6994–7112. https://doi.org/10.1021/acs.chemrev.8b00791.Search in Google Scholar PubMed
(b) Shiri, P. An overview on the copper-promoted synthesis of five membered heterocyclic systems. Appl Organomet Chem 2020;34:e5600.10.1002/aoc.5600Search in Google Scholar
11(a). Sambiagio, C, Marsden, SP, Blacker, AJ, McGowan, PC. Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development. Chem Soc Rev 2014;43:3525–50. https://doi.org/10.1039/c3cs60289c.Search in Google Scholar PubMed
(b) Klapars, A, Parris, S, Anderson, KW, Buchwald, SL. Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed C− N bond formation− ring-expansion process. J Am Chem Soc 2004;126:3529–33. https://doi.org/10.1021/ja038565t.Search in Google Scholar PubMed
12. Ackermann, L. General and efficient indole syntheses based on catalytic amination reactions. Org Lett 2005;7:439–42. https://doi.org/10.1021/ol047649j.Search in Google Scholar PubMed
13(a). Govada, GV, Reddy, SR. A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines. Appl Organomet Chem 2022;36: e6518. https://doi.org/10.1002/aoc.6518.Search in Google Scholar
(b) Bao, W, Liu, Y, Lv, X, Qian, W. Cu2O-Catalyzed tandem ring-opening/coupling cyclization process for the synthesis of 2, 3-dihydro-1, 4-benzodioxins. Org Lett 2008;10:3899–902. https://doi.org/10.1021/ol801444p.Search in Google Scholar PubMed
14. Cacchi, S, Fabrizi, G, Parisi, LM. 2-Aryl and 2-heteroaryl indoles from 1-alkynes and o-iodotrifluoroacetanilide through a domino copper-catalyzed coupling− cyclization process. Org Lett 2003;5:3843–6. https://doi.org/10.1021/ol035378r.Search in Google Scholar PubMed
15. Patil, NT, Raut, VS, Kavthe, RD, Reddy, VV, Raju, P. Thorpe–Ingold effect in copper (II)-catalyzed formal hydroalkoxylation–hydroarylation reaction of alkynols with indoles. Tetrahedron Lett 2009;50:6576–9. https://doi.org/10.1016/j.tetlet.2009.09.057.Search in Google Scholar
16. Ihara, M. Cascade reactions for syntheses of heterocycles. arkivoc 2006:416–38. https://doi.org/10.3998/ark.5550190.0007.730.Search in Google Scholar
17. Patil, NT, Raut, VS. Cooperative catalysis with metal and secondary amine: synthesis of 2-substituted quinolines via addition/cycloisomerization cascade. J Org Chem 2010;75:6961–4. https://doi.org/10.1021/jo101103a.Search in Google Scholar PubMed
18. Patil, NT. New linearly and angularly fused quinazolinones: synthesis through gold(I)-catalyzed cascade reactions and anticancer activities. Eur J Org Chem 2012:1790–9. https://doi.org/10.1002/ejoc.201101822.Search in Google Scholar
19. Feng, E, Huang, H, Zhou, Y, Ye, D, Jiang, H, Liu, H. Copper (I)-Catalyzed one-pot synthesis of 2 H-1, 4-benzoxazin-3-(4 H)-ones from o-halophenols and 2-chloroacetamides. J Org Chem 2009;74:2846–9. https://doi.org/10.1021/jo802818s.Search in Google Scholar PubMed
20(a). Priyanka, M, Krishnaraj, P, Jayachandra, R, Reddy, SR. Naturally derived sugar-based ionic liquids: an emerging tool for sustainable organic synthesis and chiral recognition. New J Chem 2021,45, 20075-90.10.1039/D1NJ03914HSearch in Google Scholar
(b) Naidu, S, Reddy, SR. A green and recyclable copper and ionic liquid catalytic system for the construction of poly-heterocyclic compounds via one-pot tandem coupling reaction. ChemistrySelect 2017;2:1196–201. https://doi.org/10.1002/slct.201601872.Search in Google Scholar
21. Lian, Y, Hummel, JR, Bergman, RG, Ellman, JA. Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-Catalyzed amination/cyclization/aromatization cascade. J Am Chem Soc 2013;135:12548–51. https://doi.org/10.1021/ja406131a.Search in Google Scholar PubMed PubMed Central
22. Patel, RM, Argade, NP. Palladium-promoted [2 + 2 + 2] cocyclization of arynes and unsymmetrical conjugated dienes: synthesis of justicidin B and retrojusticidin B. Org Lett 2013;15:14–7. https://doi.org/10.1021/ol3028658.Search in Google Scholar PubMed
23. Paul, S, Pradhan, K, Ghosh, S, De, SK, Das, AR. Uncapped SnO2 quantum dot catalyzed cascade assembling of four components: a rapid and green approach to the pyrano[2,3-c]pyrazole and spiro-2-oxindole derivatives. Tetrahedron 2014;70:6088–99. https://doi.org/10.1016/j.tet.2014.02.077.Search in Google Scholar
24. Nagarajan, RNP. Direct self control (DSC) of induction machine utilizing 3-level cascade H-bridge multilevel inverter. In: 2014 IEEE Conf. Energy Conversion, CENCON 2014; 2014, pp. 304–9. https://doi.org/10.1109/cencon.2014.6967520.Search in Google Scholar
25. Lizarme, Y. Bioorganic & medicinal chemistry synthesis and neuroprotective activity of dictyoquinazol A and analogues. Bioorg Med Chem 2016;24:1480–7. https://doi.org/10.1016/j.bmc.2016.02.016.Search in Google Scholar PubMed
26. Liu, PQ. Highly power-efficient quantum cascade lasers. Nat Photonics 2010;4:262–5. https://doi.org/10.1038/nphoton.2009.262.Search in Google Scholar
27. Pericherla, K, Kaswan, P, Khedar, P, Khungar, B, Parang, K, Kumar, A. Copper catalyzed tandem oxidative C–H amination/cyclizations: direct access to imidazo [1, 2-a] pyridines. RSC Adv 2013;3:18923–30. https://doi.org/10.1039/c3ra43889a.Search in Google Scholar
28. Santra, S, Bagdi, AK, Majee, A, Hajra, A. Metal nanoparticles in “on-water” organic synthesis: one-pot nano CuO catalyzed synthesis of isoindolo [2, 1-a] quinazolines. RSC Adv 2013;3:24931–5. https://doi.org/10.1039/c3ra43917h.Search in Google Scholar
29. Zhang, X, Li Hu, W, Chen, S, Guo Hu, X. Cu-catalyzed synthesis of fluoroalkylated isoxazoles from commercially available amines and alkynes. Org Lett 2018;20:860–3. https://doi.org/10.1021/acs.orglett.7b04028.Search in Google Scholar PubMed
30. Qi, C, Zheng, C, Rong, H, Zhong, T. Direct construction of acid-responsive poly(indolone)s through multicomponent tandem polymerizations. ACS Macro Lett 2019;8:569–75. https://doi.org/10.1021/acsmacrolett.9b00297.Search in Google Scholar PubMed
31. Éric, G, Jeffrey, S, Antoine, C, Shawn, KC. General Cu-catalyzed Csp−S coupling. Org Lett 2020;22:5905–9.10.1021/acs.orglett.0c02004Search in Google Scholar PubMed
32. Yuzhang, H, Liguo, X, Rongrong, H, Ben Zhong, T. Cu(I)-catalyzed heterogeneous multicomponent polymerizations of alkynes, sulfonyl azides, and NH4Cl. Macromolecules 2020;53:10366–74.10.1021/acs.macromol.0c02139Search in Google Scholar
33. Liguo, X, Zhou, T, Min, L, Rongrong, H, Ben Zhong, T. Multicomponent polymerizations of alkynes, sulfonyl azides, and 2-hydroxybenzonitrile/2-aminobenzonitrile towards multifunctional iminocoumarin/quinoline-containing poly(N-sulfonylimine) s. ACS Macro Lett 2019;8:101–6.10.1021/acsmacrolett.8b00884Search in Google Scholar PubMed
34. Ki-Taek, B, Kim, H, Kang, S, Bhaumik, A, Ahn, S, Yun, N, et al.. Constructing a library of doubly grafted polymers by a one-shot Cu-catalyzed multicomponent grafting strategy. Macromolecules 2021;54:5539–48.10.1021/acs.macromol.1c00440Search in Google Scholar
35. Lin, J, Zheng, T, Quan Fan, N, Zhang, P, Jiang, K, Wei, Y. Pyrrole synthesis through Cu-catalyzed cascade [3 + 2] spiroannulation/aromatization of oximes with azadienes. Org Chem Front 2021;8:3776–82. https://doi.org/10.1039/d1qo00443c.Search in Google Scholar
© 2022 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Reviews
- Anticancer properties of arylchromenes and arylchromans: an overview
- Solid state lithium ion conductors for lithium batteries
- Performance and kinetics of a fluidized bed anaerobic reactor treating distillery effluent
- Use of biochemical markers for diabetes prevention in the new decade
- Antibreast cancer activities of phytochemicals from Anonna muricata using computer-aided drug design (CADD) approach
- Alkaline-earth metal(II) complexes of salinomycin – spectral properties and antibacterial activity
- Use of heterogeneous catalysis in sustainable biofuel production
- Antibacterial, antioxidant and cytotoxic activities of the stem bark of Archidendron jiringa (Jack) I.C. Nielsen
- A review of sludge production in South Africa municipal wastewater treatment plants, analysis of handling cost and potential minimization methods
- Cu-Catalysed tandem reactions for building poly hetero atom heterocycles-green chemistry tool
- Optimizing Cr(VI) adsorption parameters on magnetite (Fe3O4) and manganese doped magnetite (MnxFe(3-x)O4) nanoparticles
- Fabaceae: a significant flavonoid source for plant and human health
- A novel application of synthesised based squarylium dyes on nylon 6, and silk woven fabrics
- Chromatographic characterization of the fusion protein SARS-CoV-2 S protein (RBD)-hFc
- Ethnopharmacology, phytochemistry and a new chemotaxonomic marker in Oldenlandia affinis (Roem. & Schult.) DC. Rubiaceae
- Extraction, isolation and characterization of secondary metabolites in the leaves of Morinda lucida from Oshiegbe in Ebonyi State
- Lead optimisation efforts on a molecular prototype of the immunomodulatory parasitic protein ES-62
- Catalytic applications of graphene oxide towards the synthesis of bioactive scaffolds through the formation of carbon–carbon and carbon–heteroatom bonds
- Synthesis, characterization, DFT and molecular docking studies of acetone O-((2,5-dichlorophenyl)sulfonyl) oxime
- Design of membrane systems
- Conceptual design and cost-efficient environmentally Benign synthesis of beta-lactams
- Synthesis and characterization of alkaloid derived hydrazones and their metal (II) complexes
- The spontaneity of chemical reactions: challenges with handling the concept and its implications
- Copper nanoparticles catalyzed carbon–heteroatom bond formation and synthesis of related heterocycles by greener procedures
- Tellurium in carbohydrate synthesis
- Conformational preferences and intramolecular hydrogen bonding patterns of tetraflavaspidic acid BBBB – a tetrameric acylphloroglucinol
- Phytochemical and antioxidant studies of Hibiscus Cannabinus seed oil
- Polyaniline mediated heterogeneous catalysis in the preparation of heterocyclic derivatives through carbon–heteroatom bond formations
- A comparison of two digestion methods and heavy metals determination in sediments
- Synthesis, properties and catalysis of quantum dots in C–C and C-heteroatom bond formations
- Recyclable magnetically retrievable nanocatalysts for C–heteroatom bond formation reactions
- Small molecules as next generation biofilm inhibitors and anti-infective agents
- Toxicity of tellurium and its compounds
- Biodegradable polycaprolactone (PCL) based polymer and composites
- Quality of poultry meat- the practical issues and knowledge based solutions
Articles in the same Issue
- Frontmatter
- Reviews
- Anticancer properties of arylchromenes and arylchromans: an overview
- Solid state lithium ion conductors for lithium batteries
- Performance and kinetics of a fluidized bed anaerobic reactor treating distillery effluent
- Use of biochemical markers for diabetes prevention in the new decade
- Antibreast cancer activities of phytochemicals from Anonna muricata using computer-aided drug design (CADD) approach
- Alkaline-earth metal(II) complexes of salinomycin – spectral properties and antibacterial activity
- Use of heterogeneous catalysis in sustainable biofuel production
- Antibacterial, antioxidant and cytotoxic activities of the stem bark of Archidendron jiringa (Jack) I.C. Nielsen
- A review of sludge production in South Africa municipal wastewater treatment plants, analysis of handling cost and potential minimization methods
- Cu-Catalysed tandem reactions for building poly hetero atom heterocycles-green chemistry tool
- Optimizing Cr(VI) adsorption parameters on magnetite (Fe3O4) and manganese doped magnetite (MnxFe(3-x)O4) nanoparticles
- Fabaceae: a significant flavonoid source for plant and human health
- A novel application of synthesised based squarylium dyes on nylon 6, and silk woven fabrics
- Chromatographic characterization of the fusion protein SARS-CoV-2 S protein (RBD)-hFc
- Ethnopharmacology, phytochemistry and a new chemotaxonomic marker in Oldenlandia affinis (Roem. & Schult.) DC. Rubiaceae
- Extraction, isolation and characterization of secondary metabolites in the leaves of Morinda lucida from Oshiegbe in Ebonyi State
- Lead optimisation efforts on a molecular prototype of the immunomodulatory parasitic protein ES-62
- Catalytic applications of graphene oxide towards the synthesis of bioactive scaffolds through the formation of carbon–carbon and carbon–heteroatom bonds
- Synthesis, characterization, DFT and molecular docking studies of acetone O-((2,5-dichlorophenyl)sulfonyl) oxime
- Design of membrane systems
- Conceptual design and cost-efficient environmentally Benign synthesis of beta-lactams
- Synthesis and characterization of alkaloid derived hydrazones and their metal (II) complexes
- The spontaneity of chemical reactions: challenges with handling the concept and its implications
- Copper nanoparticles catalyzed carbon–heteroatom bond formation and synthesis of related heterocycles by greener procedures
- Tellurium in carbohydrate synthesis
- Conformational preferences and intramolecular hydrogen bonding patterns of tetraflavaspidic acid BBBB – a tetrameric acylphloroglucinol
- Phytochemical and antioxidant studies of Hibiscus Cannabinus seed oil
- Polyaniline mediated heterogeneous catalysis in the preparation of heterocyclic derivatives through carbon–heteroatom bond formations
- A comparison of two digestion methods and heavy metals determination in sediments
- Synthesis, properties and catalysis of quantum dots in C–C and C-heteroatom bond formations
- Recyclable magnetically retrievable nanocatalysts for C–heteroatom bond formation reactions
- Small molecules as next generation biofilm inhibitors and anti-infective agents
- Toxicity of tellurium and its compounds
- Biodegradable polycaprolactone (PCL) based polymer and composites
- Quality of poultry meat- the practical issues and knowledge based solutions