Bismuth nitrate as an efficient recyclable catalyst for the one-pot multi component synthesis of 1,4-dihydropyridine derivatives through unsymmetrical Hantzsch reaction

Journal of Saudi Chemical Society

Volumn 20, Issue , 2016, Pages S100-S108

  Sheik Mansoor, S ^a   Aswin, K ^a   Logaiya, K ^a   Sudhan, S P N ^a  

^a C ABDUL HAKEEM COLLEGE   (India)

Author keywords

1,4 Dihydropyridine; Bismuth nitrate; Hantzsch reaction; Multi component reaction; One pot synthesis

Indexed keywords

EID: 84869872973     PISSN: 13196103     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jscs.2012.09.010     Document Type: Article

References (45)

1. Ahluwalia, V.K., Goyal, B., Das, U., J. Chem. Res. Mini-print, 7, 1997, 1701.
2. Brahmachari, G., Das, S., Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature. Tetrahedron Lett. 53 (2012), 1479–1484.
3. Bandyopadhyay, D., Mukherjee, S., Granados, J.C., Short, J.D., Banik, B.K., Ultrasound-assisted bismuth nitrate-induced green synthesis of novel pyrrole derivatives and their biological evaluation as anticancer agents. Eur. J. Med. Chem. 50 (2012), 209–215.
4. Bertozzi, F., Gustafsson, M., Olsson, R., A Novel Metal-Iodide Promoted Three-Component Synthesis of Substituted Pyrrolidines. Org. Lett. 4 (2002), 3147–3150.
5. Bagley, M.C., Dale, J.W., Bower, J., A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines. Chem. Commun., 2002, 1682–1683.
6. Cherkupally, S.R., Mekalan, R., p-TSA catalyzed facile and efficient synthesis of polyhydroquinoline derivatives through hantzsch multi-component condensation. Chem. Pharm. Bull. 56 (2008), 1002–1004.
7. Das, B., Ravikanth, B., Ramu, R., Rao, B.V., An efficient one-pot synthesis of polyhydroquinolines at room temperature using HY-zeolite. Chem. Pharm. Bull. 54 (2006), 1044–1045.
8. Desai, B., Sureja, D., Naliapara, Y., Shah, A., Saxena, A.K., Synthesis and QSAR Studies of 4-Substituted phenyl-2,6-dimethyl-3, 5-bis-N-(substituted phenyl)carbamoyl-1,4-dihydropyridines as potential antitubercular agents. Bioorg. Med. Chem. 9 (2001), 1993–1998.
9. Donelson, J.L., Gibbs, R.A., De, S.K., An efficient one-pot synthesis of polyhydroquinoline derivatives through the Hantzsch four component condensation. J. Mol. Catal. A: Chem. 256 (2006), 309–311.
10. Domling, A., Ugi, I., Multicomponent Reactions with Isocyanides. Angew. Chem. Int. Ed. 39 (2000), 3168–3210.
11. Eharkar, P.S., Desai, B., Gaveria, H., Varu, B., Loriya, R., Naliapara, Y., Shah, A., Kulkarni, V.M., Three-dimensional quantitative structure-activity relationship of 1,4-dihydropyridines as antitubercular agents. J. Med. Chem. 45 (2002), 4858–4867.
12. Gaudio, A.C., Korolkovas, A., Takahata, Y., Quantitative structure-activity relationships for 1,4-dihydropyridine calcium channel antagonists (nifedipine analogues): A quantum chemical/classical approach. J. Pharm. Sci. 83 (1994), 1110–1115.
13. Hantzsch, A., Ueber die synthese pyridinartiger verbindungen aus acetessigather und aldehydammoniak. Liebigs Ann. Chem. 215 (1882), 1–82.
14. 40]-catalyzed one-pot synthesis of polyhydroquinoline derivatives via the Hantzsch three component condensation. J. Mol. Catal. A: Chem. 264 (2007), 50–52.
15. Ji, S.J., Jiang, Z.Q., Lu, J., Loh, T.P., Facile ionic liquids-promoted one-pot synthesis of polyhydroquinoline derivatives under solvent-free condition. Synlett, 2004, 831–835.
16. Ko, S., Yao, C.F., Ceric Ammonium Nitrate (CAN) catalyzes the one-pot synthesis of polyhydroquinoline via the Hantzsch reaction. Tetrahedron 62 (2006), 7293–7299.
17. Kumar, S., Sharma, P., Kapoor, K.K., Hundal, M.S., An efficient, catalyst- and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding. Tetrahedron 64 (2008), 536–542.
18. Karade, N.N., Budhewar, V.H., Shinde, S.V., Jadhav, W.N., L-Proline as an Efficient Organo-Catalyst for the Synthesis of Polyhydroquinoline via Multicomponent Hantzsch Reaction. Lett. Org. Chem. 4 (2007), 16–19.
19. Kumar, R.S., Idhayadhulla, A., Nasser, A.J.A., Selvin, J., Synthesis and antimicrobial activity of a new series of 1,4-dihydropyridine derivatives. J. Serb. Chem. Soc. 76 (2011), 1–11.
20. Kirschbaum, J., Biological oxidations and energy conservation. J. Chem. Educ. 45 (1968), 28–36.
21. Margarita, S., Estael, O., Yamila, V., Beatriz, P., Lourdes, M., Margarita, Q., Jose, L.S., Hector, N., Norbert, B., Oswald, M.P., A joint experimental and theoretical structural study of novel substituted 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines. Tetrahedron 55 (1999), 875–884.
22. Maheswara, M., Siddaiah, V., Damu, G.L., Rao, C.V., An efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation using a heterogeneous catalyst under solvent-free conditions. ARKIVOC 2 (2006), 201–206.
23. 2O: Investigating the role of the catalyst. C. R. Chim. 14 (2011), 944–952.
24. Mansoor, S.S., Shafi, S.S., Ahmed, S.Z., An efficient one-pot multicomponent synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones/imines via a Lewis base catalyzed Biginelli-type reactionunder solvent-free conditions. Arab J. Chem., 2011 doi: 10.1016/j.arabjc.2011.09.018.
25. Mansoor, S.S., Aswin, K., Logaiya, K., Sudhan, S.P.N., An efficient synthesis of β-amino ketone compounds through one-pot three-component Mannich-type reactions using bismuth nitrate as catalyst. J. Saudi Chem. Soc. 19:4 (2015), 379–386.
26. 2O: An efficient and recyclable catalyst for the three-component synthesis of amidoalkyl naphthols under solvent-free conditions. J. Saudi Chem. Soc. 20:2 (2016), 138–150.
27. Norcross, B.E., Klinedinst, P.E., Westheimer, F.H., The reduction of olefnic double bonds with dihydropyridines. J. Am. Chem. Soc. 84 (1962), 797–802.
28. Ohberg, L., Westman, J., Microwave assisted simple synthesis of dihydropyridine in presences of aqueous ammoniumhydroxide. Synlett, 2001, 1296–1298.
29. 4(H)]: A mild and efficient recyclable catalyst for one-pot synthesis of polyhydroquinoline via the Hantzsch reaction under solvent-free conditions. J. Heterocycl. Chem. 49 (2012), 232–236.
30. 3H as a nanoreactor for the one-pot, solvent-free synthesis of 1,8-dioxo-9-aryl decahydroacridines. J. Heterocycl. Chem. 49 (2012), 111–115.
31. Rivera, S., Bandyopadhyay, D., Banik, B.K., Facile synthesis of N-substituted pyrroles via microwave-induced bismuth nitrate-catalyzed reaction. Tetrahedron Lett. 50 (2009), 5445–5448.
32. Ravi, P., Tewari, S., Facile and environmentally friendly synthesis of nitropyrazoles using montmorillonite K-10 impregnated with bismuth nitrate. Catal. Commun. 19 (2012), 37–41.
33. Song, G., Wang, B., Wu, X., Kang, Y., Yang, L., Montmorillonite K10 clay: An effective solid catalyst for one-pot synthesis of polyhydroquinoline derivatives. Synth. Commun. 35 (2005), 2875–2880.
34. Sabitha, G., Reddy, G.S.K.K., Reddy, C.S., Yadav, J.S., A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature. Tetrahedron Lett. 44 (2003), 4129–4131.
35. Sridhar, R., Perumal, P.T., A new protocol to synthesize 1,4-dihydropyridines by using 3,4,5-trifluorobenzeneboronic acid as a catalyst in ionic liquid: synthesis of novel 4-(3-carboxyl-1H-pyrazol-4-yl)-1,4-dihydropyridines. Tetrahedron 61 (2005), 2465–2470.
36. Sapkal, S.B., Shelke, K.F., Shingate, B.B., Shingare, M.S., Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions. Tetrahedron Lett. 50 (2009), 1754–1756.
37. 3 as a Novel Catalyst for the Synthesis of Polyhydroquinoline Derivatives via Unsymmetrical Hantzsch Reaction. J. Fluorine Chem. 135 (2012), 91–96.
38. Schellenberg, K.A., Weheimer, F.H., A free radical oxidation of dihydropyridines. J. Org. Chem. 30 (1965), 1859–1862.
39. Stout, D.M., Meyers, A.I., Recent advances in the chemistry of dihydropyridines. Chem. Rev. 82 (1982), 223–243.
40. Swarnalatha, G., Prasanthi, G., Sirisha, N., Chetty, C.M., 1,4-Dihydropyridines: A Multtifunctional Molecule- A Review. Int. J. Chem. Tech. Res. 3:1 (2011), 75–89.
41. Tanabe, H., Tasaka, S., Ohmori, H., Gomi, N., Sasaki, Y., Machida, T., Iino, M., Kiue, A., Naito, S., Kuwano, M., Newly synthesized dihydropyridine derivatives as modulators of P-Glycoprotein-mediated multidrug resistance. Bioorg. Med. Chem. 6 (1998), 2219–2227.
42. Tasaka, S., Ohmori, H., Gomi, N., Iino, M., Machida, T., Kiue, A., Naito, S., Kuwano, M., Synthesis and structure–activity analysis of novel dihydropyridine derivatives to overcome multidrug resistance. Bioorg. Med. Chem. Lett. 11 (2001), 275–277.
43. Wang, M., Liang, Y., Zhang, T.T., Gao, J., Three-component synthesis of amidoalkyl naphthols catalyzed by bismuth(III) nitrate pentahydrate. J. Chin. Chem. Lett. 23 (2012), 65–68.
44. 3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction. Tetrahedron 61 (2005), 1539–1543.
45. Zhu, J., Bienayme, H., Multicomponent Reactions. 2005, Wiley-VCH, Weinheim.