Polyaniline mediated heterogeneous catalysis in the preparation of heterocyclic derivatives through carbon–heteroatom bond formations
-
Jayathirtha Rao Vaidya
and
Yadavalli Venkata Durga Nageswar
Abstract
Green-bond forming reactions in organic chemistry are very much essential for the sustainability and it is a continuous evolutionary process. Polyaniline (PANI) is one of the catalysts can offer a green-bond forming chemistry. The present chapter is designed to explain PANI mediated reactions leading to the synthesis of heterocycles. PANI and PANI-doped catalyst preparation methods and together with characterization of PANI catalyst using modern analytical tools is explained. Several heterocycles were prepared using PANI or doped-PANI catalyst in a one pot reaction conditions or sometimes multicomponent reaction conditions. Ease of PANI preparation, simple reaction conditions, PANI recovery and reusability and quick-way of product isolation or workup procedure are the highlights of this chapter.
Acknowledgment
VJR thank CSIR-New Delhi for the Emeritus Scientist Honor.
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: None declared.
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Boeva, ZA, Sergeyev, VG. Polyaniline: synthesis, properties, and application. Polym Sci Ser C 2014;56:144–53. https://doi.org/10.1134/S1811238214010032.Search in Google Scholar
2. María Mota, L, Carrillo, A, Ana Verdugo, J, Olivas, A, JorgeGuerrero, M, De la Cruz, E, et al.. Synthesis and novel purification process of PANI and PANI/Ag-NPs composite. Molecules 2019;24:1621. https://doi.org/10.3390/molecules24081621.Search in Google Scholar PubMed PubMed Central
3. Sui, X, Chu, Y, Xing, S, Liu, C. Synthesis of PANI/AgCl, PANI/BaSO4 and PANI/TiO2 nanocomposites in CTAB/hexanol/water reverse micelle. Mater Lett 2004;58:1255–9. https://doi.org/10.1016/j.matlet.2003.09.035.Search in Google Scholar
4. Wang, K, Deng, Z-H, Xie, S-J, Zhai, D-D, Fang, H-Y, Shi, Z-J. Synthesis of arylamines and N-heterocycles by direct catalytic nitrogenation using N2. Nat Commun 2021;12:248. https://doi.org/10.1038/s41467-020-20270-5.Search in Google Scholar PubMed PubMed Central
5. Vasant Chabukswar, V, Kalpana Handore, N, Sanjay Bhavsar, V, Amit Horne, S, Dallavalle, S, Gaikwad, V, et al.. Conducting polyaniline is an efficient catalyst for synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivative under solvent-free conditions. J Macromol Sci, Pure Appl Chem 2013;50:411–5. https://doi.org/10.1080/10601325.2013.768157.Search in Google Scholar
6. Dutta, A, Rahman, N, Elisa Kumar, J, 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.Search in Google Scholar
7. Wang, D, Astruc, D. Fast-growing field of magnetically recyclable nanocatalysts. Chem Rev 2014;114:6949–85. https://doi.org/10.1021/cr500134h.Search in Google Scholar PubMed
8. Moriuchi, T, Hirao, T, Oshiro, Y, Ikeda, I. An efficient epoxidation with molecular oxygen catalyzed by iron complex of multidentate n-heterocyclic podand ligand. additive effect of 4-ethoxycarbonyl-3-methyl-2-cyclohexene-1-one. Chem Lett 1994:915–8.10.1246/cl.1994.915Search in Google Scholar
9. Gangadasu, B, Palaniappan, S, Rao, VJ. One-pot synthesis of dihydropyrimidinones using polyaniline–bismoclite complex. A facile and reusable catalyst for the Biginelli reaction. Synlett 2004:1285–7. https://doi.org/10.1055/s-2004-822925.Search in Google Scholar
10. Srinivas, U, Srinivas, C, Narender, P, Rao, VJ, Palaniappan, S. Polyaniline-sulfate salt as an efficient and reusable catalyst for the synthesis of 1,5-benzodiazepines and 2-phenyl benzimidazoles. Catal Commun 2007;8:107–10. https://doi.org/10.1016/j.catcom.2006.05.022.Search in Google Scholar
11. Abdollahi-Alibeik, M, Moosavifard, M. FeCl3-doped polyaniline nanoparticles as reusable heterogeneous catalyst for the synthesis of 2-substituted benzimidazoles. Synth Commun 2010;40:2686–95. https://doi.org/10.1080/00397910903318658.Search in Google Scholar
12. He, M, Liu, C, Luo, G. Synthesis and characterization of Lewis acid doped polyaniline and its application as catalysts for acetalization of carbonyl compound. Polym Plast Technol Eng 2007;46:145. https://doi.org/10.1080/03602550601152952.Search in Google Scholar
13. Zhu, C, Cakmak, U, Sheikhnejad, O, Cheng, X, Zhang, X, Xu, Y, et al.. One step synthesis of PANI/Fe2O3 nanocomposites and flexible film for enhanced NH3 sensing performance at room temperature. Nanotechnology 2019;30:255502. https://doi.org/10.1088/1361-6528/ab0.Search in Google Scholar
14. Yang, C, Du, J, Peng, Q, Qiao, R, Chen, W, Xu, C, et al.. Polyaniline/Fe3O4 nanoparticle composite: synthesis and reaction mechanism. J Phys Chem 2009;113:5052–8. https://doi.org/10.1021/jp811125k.Search in Google Scholar PubMed
15. Zhou, H, Wang, X, Yu, K, Zhang, C, Li, H, Du, H. Preparation of multi-walled carbon nanotube/polyaniline/Fe3O4 composites. Integr Ferroelectr 2014;154:159–65. https://doi.org/10.1080/10584587.2014.904706.Search in Google Scholar
16. Hojati, SF, Amiri, A, Mohamadi, S, Eghbali, NM. Novel organometallic nanomagnetic catalyst for multicomponent synthesis of spiroindoline derivatives. Res Chem Intermed 2017;44:2275–87. https://doi.org/10.1007/s11164-017-3228-5.Search in Google Scholar
17. Janošević, A, Pašti, I, Gavrilov, N, Mentus, S, Krstić, J, Mitrić, M, et al.. Microporous conducting carbonized polyaniline nanorods: synthesis,characterization and electrocatalytic properties. Microporous Mesoporous Mater 2012;152:50–7. https://doi.org/10.1016/j.micromeso.2011.12.002.Search in Google Scholar
18. Janošević, A, Ćirić-Marjanović, G, Marjanović, B, Trchová, M, Stejskal, M. 3,5-Dinitrosalicylic acid-assisted synthesis of self-assembled polyaniline nanorods. Mater Lett 2010;64:2337–40. https://doi.org/10.1016/j.matlet.2010.07.041.Search in Google Scholar
19. Yelwande, AA, Arbad, BR, Lande, MK. Polyaniline/SiO2 catalyzed one-pot synthesis of tetrahydrobenzo[b]pyran derivatives. S Afr J Chem 2010;63:199–203.Search in Google Scholar
20. Saadat, S, Nazari, S, Afshari, M, Shahabi, M, Keshavarz, M. Copper (I) iodide nanoparticles on polyaniline as a green, recoverable and reusable catalyst for multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles. Orient J Chem 2015;31:1–8. https://doi.org/10.13005/ojc/310248.Search in Google Scholar
21. Houdayer, A, Schneider, R, Billaud, D, Ghanbaja, J, Lambert, J. Heck and Suzuki–Miyaura couplings catalyzed by nanosized palladium in polyaniline. Appl Organomet Chem 2005;19:1239–48. https://doi.org/10.1002/aoc.999.Search in Google Scholar
22. Srinivas, C, Sai Pavan Kumar, CNS, Rao, VJ, Palaniappan, S. Green approach for the synthesis of quinoxaline derivativesin water medium using reusable polyaniline-sulfate salt catalyst and sodium laurylsulfate. Catal Lett 2008;121:291–6. https://doi.org/10.1007/s10562-007-9335-y.Search in Google Scholar
23. Yelwande, A, Navgire, M, Arbad, B, Lande, M. Polyaniline/SiO2 nanocomposite catalyzed efficient synthesis of quinoxaline derivatives at room temperature. J Chin Chem Soc 2012;59:995–1000. https://doi.org/10.1002/jccs.201100482.Search in Google Scholar
24. Boddula, R, Srinivasan, P. Use of iodine doped polyaniline salt in the stereoselective synthesis of 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives. Catal Commun 2013;30:56–60. https://doi.org/10.1016/j.catcom.2012.11.002.Search in Google Scholar
25. Gangadasu, B, Palaniappan, S, Amarnath, CA, Rao, VJ. Polyaniline salts and complexes: efficient and reusable catalyst for the one-pot synthesis of 5-(methoxycarbonyl)-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1h)-one. J Appl Polym Sci 2006;102:1741–5. https://doi.org/10.1002/app.24374.Search in Google Scholar
26. Lakshmi Kantam, M, Roy, M, Roy, S, Sreedhar, B, Lal De, R. Polyaniline supported CuI: an efficient catalyst for C–N bond formation by N-arylation of N(H)-heterocycles and benzyl amines with aryl halides and arylboronic acids, and aza-Michael reactions of amines with activated alkenes. Catal Commun 2008;9:2226–30. https://doi.org/10.1016/j.catcom.2008.04.0.Search in Google Scholar
27. Choudary, BM, Roy, M, Roy, S, Lakshmi Kantam, M, Sreedhar, B, Kumar, KV. Preparation, characterization and catalytic properties of polyaniline supported metal complexes. Adv Synth Catal 2006;348:1734–42. https://doi.org/10.1002/adsc.200606077.Search in Google Scholar
28. Devi, CL, Rao, VJ, Palaniappan, S. PANI-HBF4: a reusable polymer-based solid acid catalyst for three-component, one-pot synthesis of 3-substituted amino methyl indoles under solvent-free conditions. Synth Commun 2012;42:1593–603. https://doi.org/10.1080/00397911.2010.542535.Search in Google Scholar
29. Palaniappan, S, John, A. A novel polyaniline-fluoroboric acid-dodecylhydrogen sulfate salt: versatile reusable polymer-based solid acid catalyst for organic transformations. J Mol Catal Chem 2005;233:9–15. https://doi.org/10.1016/j.molcata.2005.02.002.Search in Google Scholar
30. Ju, P, Chen, J, Chen, A, Chen, L, Yu, Y. N-formylation of amines with CO2 and H2 using Pd−Au bimetallic catalysts supported on polyaniline-functionalized carbon nanotubes. ACS Sustainable Chem Eng 2017;5:2516–28. https://doi.org/10.1021/acssuschemeng.6b02865.Search in Google Scholar
31. Marx, S, Baiker, A. Beneficial interaction of gold and palladium in bimetallic catalysts for the selective oxidation of benzyl alcohol. J Phys Chem C 2009;113:6191–201. https://doi.org/10.1021/jp808362m.Search in Google Scholar
32. Bahuguna, A, Choudhary, P, Chhabra, T, Krishnan, V. Ammonia-doped polyaniline−graphitic carbon nitride nanocomposite as a heterogeneous green catalyst for synthesis of indole-substituted 4H-chromenes. ACS Omega 2018;3:12163–78. https://doi.org/10.1021/acsomega.8b01687.Search in Google Scholar PubMed PubMed Central
33. Raziq, F, Qu, Y, Zhang, X, Humayun, M, Wu, J, Zada, A, et al.. Enhanced cocatalyst-free visible-light activities for photocatalytic fuel production of g-C3N4 by trapping holes and transferring electrons. J Phys Chem C 2016;120:98–107. https://doi.org/10.1021/acs.jpcc.5b10313.Search in Google Scholar
34. Abu-Thabit, NY. Chemical oxidative polymerization of polyaniline: a practical approach for preparation of smart conductive textiles. J Chem Educ 2016;93:1606–11. https://doi.org/10.1021/acs.jchemed.6b00060.Search in Google Scholar
35. Siddiqui, S, Zeba Siddiqui, N. Copper Schiff base functionalized polyaniline (Cu-SB/PANI): a highly efficient polymer based organometallic catalyst for the synthesis of 2-amino chromene derivatives. Appl Organomet Chem 2019:e5161. https://doi.org/10.1002/aoc.5161.Search in Google Scholar
36. Palaniappan, S, John, A, Amarnath, CA, Rao, VJ. Mannich type reaction in solvent free condition using reusable polyaniline catalyst. J Mol Catal Chem 2004;218:47–53. https://doi.org/10.1016/j.molcata.2004.04.010.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
