An efficient one-pot three-component synthesis of α-amino nitriles via Strecker reaction catalysed by bismuth(III) nitrate

Journal of Saudi Chemical Society

Volumn 20, Issue , 2016, Pages S202-S210

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

^a C ABDUL HAKEEM COLLEGE   (India)

Author keywords

Amino nitriles; Bismuth nitrate; One pot synthesis; Strecker reaction

Indexed keywords

EID: 84870728988     PISSN: 13196103     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jscs.2012.10.009     Document Type: Article

References (61)

1. Alexander, V.M., Bhat, R.P., Samant, S.D., Bismuth(III) nitrate pentahydrate-a mild and inexpensive reagent for synthesis of coumarins under mild conditions. Tetrahedron Lett. 46 (2005), 6957–6959.
2. Arasappan, A., Venkatraman, S., Padilla, A.I., Wu, W., Meng, T., Jin, Y., Wong, J., Prongay, A., Girijavallabhan, V., Njoroge, G.F., Practical and efficient method for amino acid derivatives containing β-quaternary center: application toward synthesis of hepatitis C virus NS3 serine protease inhibitors. Tetrahedron Lett. 48 (2007), 6343–6347.
3. Avendano, C., Ramos, T., Gómez-Molinero, E., 2,4,4-trisubstituted 5-amino-4h-imidazoles. A new synthetic approach and reactivity. J. Heterocycl. Chem. 22 (1985), 537–540.
4. 2 P25. Chin. Chem. Lett. 22 (2011), 555–558.
5. Banik, B.K., Cardona, M., Bismuth nitrate-catalyzed novel synthesis of pyrrole-substituted Indolinones. Tetrahedron Lett. 47 (2006), 7385–7387.
6. Bhanu Prasad, B.A., Bisai, A., Singh, V.K., Trimethylsilyl cyanide addition to aldimines and its application in the synthesis of (S)-phenylglycine methyl ester. Tetrahedron Lett. 45 (2004), 9565–9567.
7. Bothwell, J.M., Krabbe, S.W., Mohan, R.S., Applications of bismuth(III) compounds in organic synthesis. Chem. Soc. Rev. 40 (2011), 4649–4707.
8. Chuit, C., Corriu, R.J.P., Reye, C., Young, J.C., Reactivity of penta- and hexacoordinate silicon compounds and their role as reaction intermediates. Chem. Rev. 93 (1993), 1371–1448.
9. Das, B., Ramu, R., Ravikanth, B., Reddy, K.R., (Bromodimethyl)sulfonium bromide catalyzed one-pot synthesis of α-aminonitriles. Synthesis, 2006, 1419–1422.
10. Das, B.C., Anguiano, J., Mahalingam, S.M., Design and synthesis of α-aminonitrile-functionalized novel retinoids. Tetrahedron Lett. 50 (2009), 5670–5672.
11. 3 catalysed one-pot synthesis of α-aminonitriles. Synth. Commun. 35 (2005), 653–656.
12. De, S.K., Gibbs, R.A., Bismuth trichloride catalyzed synthesis of α-aminonitriles. Tetrahedron Lett. 45 (2004), 7407–7408.
13. De, S.K., Gibbs, R.A., Praseodymium trifluoromethylsulfonate as an efficient and recyclable catalyst for the synthesis of α-aminonitriles. Synth. Commun. 35 (2005), 961–966.
14. Dekamin, M.G., Mokhtari, Z., Highly efficient and convenient Strecker reaction of carbonyl compounds and amines with TMSCN catalysed by MCM-41 anchored sulfonic acid as a recoverable catalyst. Tetrahedron 68 (2012), 922–930.
15. Dilman, A.D., Belyakov, P.A., Korlyukov, A.A., Struchkova, M.I., Tartakovsky, V.A., Synthesis of pentafluorophenylmethylamines via silicon Mannich reaction. Org. Lett. 7 (2005), 2913–2915.
16. Drabina, P., Sedlák, M., 2-Amino-2-alkyl(aryl)propanenitriles as key building blocks for the synthesis of five-membered heterocycles. ARKIVOC (i), 2012, 152–172.
17. Duthaler, R.O., Recent developments in the stereoselective synthesis of α-aminoacids. Tetrahedron 50 (1994), 1539–1650.
18. Dyker, G., Amino acid derivatives by multicomponent reactions. Angew. Chem. Int. Ed. 36 (1997), 1700–1702.
19. Enders, D., Shilvock, J.P., Some recent applications of α-amino nitrile chemistry. Chem. Soc. Rev. 29 (2000), 359–373.
20. Estramareix, B., David, S., Biosynthesis of thiamine: origin of the methyl carbon atom of the pyrimidine moiety in Salmonella typhimurium. Biochem. Biophys. Res. Commun. 134 (1986), 1136–1141.
21. Gómez, E., Avendano, C., McKillop, A., Ethyl carboethoxyformimidate in heterocyclic chemistry. Tetrahedron 42 (1986), 2625–2634.
22. Groutas, W.C., Felker, D., Synthetic applications of cyanotrimethylsilane, iodotrimethylsilane, azidotrimethylsilane and methylthiotrimethyl silane. Synthesis, 1980, 861–868.
23. Harusawa, S., Hamada, Y., Shioiri, T., Diethyl phosphorocyanidated (DEPC), a novel reagent for the classical Strecker's α-amino nitrile synthesis. Tetrahedron Lett. 20 (1979), 4663–4666.
24. Hua, R.M., Recent advances of bismuth(III) salts in organic chemistry. Curr. Org. Chem. 5 (2008), 1–24.
25. Iwanami, K., Seo, H., Jun-Chul Choi, Sakakura, T., Yasuda, H., Al-MCM-41 catalysed three-component Strecker-type synthesis of α-aminonitriles. Tetrahedron 66 (2010), 1898–1901.
26. 4 catalysed efficient multicomponent synthesis of α-amino nitriles in aqueous media. Tetrahedron Lett. 51 (2010), 2748–2750.
27. 4 nanoparticles as an efficient and reusable catalyst for one-pot synthesis of α-amino nitriles in water. Appl. Catal. A: Gen. 395 (2011), 28–33.
28. Kobayashi, S., Ishitani, H., Catalytic enantioselective addition to imines. Chem. Rev. 99 (1999), 1069–1094.
29. Kobayashi, S., Nagayama, S., Busujima, T., Polymer scandium-catalysed three-component reactions leading to diverse amino ketone, amino ester and amino nitrile derivatives. Tetrahedron Lett. 37 (1996), 9221–9224.
30. Kobayashi, S., Ishitani, H., Ueno, M., Facile synthesis of á-amino nitriles using Lanthanide triflate as a Lewis acid catalyst. Synlett, 1997, 115–116.
31. Kobayashi, S., Basujima, T., Nagayama, S., Scandium triflate-catalysed Strecker-type reactions of aldehydes, amines and tributyltin cyanide in both organic and aqueous solutions. Achievement of complete recovery of the tin compounds toward environmentally-friendly chemical processes. J. Chem. Soc. Chem. Commun, 1998, 981–982.
32. Leonard, N.M., Wieland, L.C., Mohan, R.S., Application of bismuth(III) compounds in organic synthesis. Tetrahedron 58 (2002), 8373–8397.
33. Majhi, A., Kim, S.S., Kadam, S.T., Rhodium(III)iodide hydrate catalysed three-component coupling reaction: synthesis of α-aminonitriles from aldehydes, amines, and trimethylsilyl cyanide. Tetrahedron 64 (2008), 5509–5514.
34. Mansoor, S.S., Shafi, S.S., Ahmed, S.Z., 2011. An efficient one-pot multicomponent synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones/imines via a Lewis base catalyzed Biginelli-type reaction under solvent-free conditions. Arab. J. Chem. http://dx.doi.org/10.1016/j.arabjc.2011.09.018.
35. Mansoor, S.S., Aswin, K., Logaiya, K., Sudhan, S.P.N., 2015. 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) 379–386.
36. 2O: an efficient and recyclable catalyst for the three-component synthesis of amidoalkyl naphthols under solvent-free conditions. J. Saudi Chem. Soc. 20 (2) 138–150.
37. 4 ionic liquid: an efficient reaction medium for the one-pot multi-component synthesis of 2-amino-4,6-diphenyl pyridine-3-carbonitrile derivatives. J. Saudi Chem. Soc. 20 (5) 517–522.
38. Mansoor, S.S., Aswin, K., Logaiya, K., Sudhan, S.P.N., 2016c. Bismuth nitrate as an efficient recyclable catalyst for the one-pot multi component synthesis of 1,4-dihydropyridine derivatives through unsymmetrical Hantzsch reaction. J. Saudi Chem. Soc. 20 (S1) S100–S108.
39. Martinez, R., Ramon, D.J., Yus, M., Catalyst-free multicomponent Strecker reaction in acetonitrile. Tetrahedron Lett. 46 (2005), 8471–8474.
40. Matier, W.L., Owens, D.A., Comer, W.T., Deitchman, D., Ferguson, H.C., Seidehamel, R.J., Young, J.R., Antihypertensive agents. Synthesis and biological properties of 2-amino-4-aryl-2-imidazolines. J. Med. Chem. 16 (1973), 901–908.
41. Mukhopadhyay, C., Datta, A., Bismuth(III) nitrate pentahydrate: a stoichiometric reagent for microwave induced mild and highly efficient aerial oxidation of aromatic aldehyde under solvent-free conditions. Catal. Commun. 9 (2008), 2588–2592.
42. 2AlCN. Tetrahedron: Asymmetry 15 (2004), 1513–1516.
43. Narasimhulu, M., Reddy, T.S., Mahesh, K.C., Reddy, S.M., Reddy, A.V., Venkateswarlu, Y.J., Lanthanum(III) nitrate hexahydrate or Gadolinium(III) chloride hexahydrate catalysed one-pot synthesis of á-amino nitriles. J. Mol. Catal. A: Chem. 264 (2007), 288–292.
44. 2 complex as a solid mild acid catalyst for efficient one pot, three component, Strecker synthesis of α-aminonitriles. Catal. Lett. 114 (2007), 1–7.
45. Oniciu, D., Balaban, T.S., Balaban, A.T., Synthesis of substituted 2-oxazolin-4-ones and imidazolin-5-ones. Rev. Roum. Chim. 37 (1992), 407–409.
46. 3N-catalysed three-component condensation of aldehydes, amines, and cyanides: a high yield synthesis of α-aminonitriles. Tetrahedron Lett. 47 (2006), 5759–5762.
47. Pasha, M.A., Nanjundaswamy, H.M., Jayashankara, V.P., Cerium(III) chloride: a highly efficient reagent for the synthesis of α-aminonitriles. Synth. Commun. 37 (2007), 4371–4380.
48. 3-Supported 12-tungstosilicic acid as an efficient heterogeneous catalyst for the synthesis of α-aminonitrile. Synth. Commun. 38 (2008), 2741–2747.
49. 4 promoted efficient one-pot synthesis of α-amino nitriles. Indian J. Chem. 48B (2009), 295–300.
50. Razafindrabe, C.R., Aubry, S., Bourdon, B., Andriantsiferana, M., Pellet-Rostaing, S., Lemaire, M., Synthesis of (±)-phthalascidin 650 analogue: new synthetic route to (±)-phthalascidin 622. Tetrahedron 66 (2010), 9061–9066.
51. Royer, L., De, S.K., Gibbs, R.A., Iodine as a novel and efficient reagent for the synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cynide. Tetrahedron Lett. 46 (2005), 4595–4597.
52. Schrimsher, J.L., Schendel, F.J., Stubbe, J., Smith, J.M., Purification and characterization of aminoimidazole ribonucleotide synthetase from Escherichia coli. Biochemistry 25 (1986), 4366–4371.
53. Shaabani, A., Maleki, A., Soudi, M.R., Mofakham, H., Xanthane sulfuric acid: a new and efficient bio-supported solid acid catalyst for the synthesis of α-amino nitriles by condensation of carbonyl compounds, amines, and trimethylsilylcyanide. Catal. Commun. 10 (2009), 945–949.
54. Shafran, Y.M., Bakulev, V.A., Mokrushin, V.S., Synthesis and properties of α-aminonitriles. Russ. Chem. Rev. 58 (1989), 148–162.
55. Shen, Z.L., Ji, S.J., Loh, T.P., Indium(III) iodide-mediated Strecker reaction in water: an efficient and environmentally friendly approach for the synthesis of α-aminonirile via a three-component condensation. Tetrahedron 64 (2008), 8159–8163.
56. Soh, C.H., Chui, W.K., Lam, Y., Synthesis of 2,4-disubstituted 5-aminoimidazoles using microwave irradiation. J. Comb. Chem. 8 (2006), 464–468.
57. Strecker, A., Ueber die Ktinstliche Bildung der. Milchsaiire und einen neuen, dem Glycocoll homologen. Krrper. Ann. Chem. Pharm. 75 (1850), 27–45.
58. Thirupathi, P., Kim, S.S., Three component synthesis of homoallylic amines catalysed by bismuth(III) nitrate pentahydrate. Tetrahedron 65 (2009), 5168–5173.
59. Vachal, P., Jacobsen, E.N., Structure-based analysis and optimisation of a highly enantioselective catalyst for the Strecker reaction. J. Am. Chem. Soc. 124 (2002), 10012–10014.
60. Wang, M., Liang, Y., Zhang, T.T., Gao, J.J., Three-component synthesis of amidoalkyl naphthols catalysed by bismuth(III) nitrate pentahydrate. Chin. Chem. Lett. 23 (2012), 65–68.
61. Yadav, J.S., Reddy, B.V.S., Eeshwaraiah, B., Srinivas, M., Montmorillonite KSF clay catalyzed one-pot synthesis of α-aminonitriles. Tetrahedron 60 (2004), 1767–1771.