A facile method for the synthesis of nicotinonitriles from ketones via a one-pot chloromethyleneiminium salt mediated three-component reaction

Tetrahedron Letters

Volumn 48, Issue 32, 2007, Pages 5641-5643

  Asokan, C V ^a   Anabha, E R ^a   Thomas, Ajith Dain ^a   Jose, Ann Maria ^a   Lethesh, K C ^a   Prasanth, M ^a   Krishanraj, K U ^a  

^a MAHATMA GANDHI UNIVERSITY   (India)

Author keywords

Knoevenagel reaction; Nicotinonitrile; Three component synthesis; Vilsmeier Haack reaction

Indexed keywords

2 CHLORONICOTINONITRILE; ACETOPHENONE; BENZYLIDENEACETONE; CHLOROMETHYLENEIMINIUM SALT; IMINE; KETONE; MALONONITRILE; NICOTINE DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ALKYLATION; AROMATIZATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; POLYMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; VILSMEIER HAACK REACTION;

EID: 34447262277     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.032     Document Type: Article

References (27)

1. Jutz C. Advances in Organic Chemistry. In: Taylor E.C. (Ed). Iminium Salts in Organic Chemistry Part I Vol. 9 (1976), John Wiley, New York 225-342
2. Meth-Cohn O., and Stanforth S.P. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1990), Pergamon Press, New York 777-794
3. Marson C.M. Tetrahedron 48 (1992) 3659
4. Jones G., and Stanforth S.P. Org. React. 56 (2000) 355
5. Josemin, Nirmala K.N., and Asokan C.V. Tetrahedron Lett. 38 (1997) 8391
6. Suma S., and Asokan C.V. Synth. Commun. 26 (1996) 847
7. Asokan C.V., and Mathews A. Tetrahedron Lett. 35 (1994) 2585
8. Chandrasekharan M., Asokan C.V., Ila H., and Junjappa H. Tetrahedron Lett. 31 (1990) 1763
9. Mahata P.K., Venkatesh C., Syam Kumar U.K., Ila H., and Junjappa H. J. Org. Chem. 68 (2003) 3966
10. Liu Y., Dong D., Liu Q., Qi Y., and Wang Z. Org. Biomol. Chem. 2 (2004) 28
11. Liu Q., Che G., Yu H., Liu Y., Zhang J., Zhang Q., and Dong D. J. Org. Chem. 68 (2003) 9148
12. Asokan C.V., Shukla J., Kumar U.K.S., Ila H., and Junjappa H. Ind. J. Chem. 40B (2001) 937
13. Arnold Z., and Zemlicka J. Collect. Czech. Chem. Commun. 24 (1959) 2385
14. Anabha E.R., and Asokan C.V. Synthesis (2006) 151
15. Thomas A.D., Josmine, and Asokan C.V. Tetrahedron 60 (2004) 5069
16. Thomas A.D., and Asokan C.V. Tetrahedron Lett. 43 (2002) 2273
17. Thomas A.D., and Asokan C.V. J. Chem. Soc., Perkin Trans. 1 (2001) 2583
18. Anabha E.R., Nirmala K.N., Thomas A., and Asokan C.V. Synthesis (2006) 428
19. Mathew P., and Asokan C.V. Tetrahedron 62 (2006) 1708
20. Mathew P., and Asokan C.V. Tetrahedron Lett. 46 (2005) 475
21. Gupton J.T., Petrich S.A., Smith L.L., Bruce M.A., Vu P., Du K.X., Dueno E.E., Jones C.R., and Sikorski J.A. Tetrahedron 52 (1996) 6879
22. Gupton J.T., Krolikowski D.A., Yu R.H., Riesinger S.W., and Sikorski J.A. J. Org. Chem. 55 (1990) 4735
23. Gupton J.T., Krolikowski D.A., Yu R.H., Vu P., Sikorski J.A., Dahl M.L., and Jones C.R. J. Org. Chem. 57 (1992) 5480
24. Petrich S.A., Hicks F.A., Wilkinson D.R., Tarrant J.G., Bruno S.M., Vargas M., Hosein K.N., Gupton J.T., and Sikorski J.A. Tetrahedron 51 (1995) 1575
25. Perez-Medina L.A., Mariella R.P., and McElvain S.M. J. Am. Chem. Soc. 69 (1947) 2574
26. 35Cl], 27), 180 (18), 179 (100), 154 (12), 152 (59), 127 (5), 125 (23), 105 (4), 99 (11), 77 (22).
27. Cyranski M.K., and Mieczkowski J. Acta Crystallogr. (1998) 1521