C2-functionalization of 1-substituted imidazoles with aldehydes and electron-deficient acetylenes: A novel three-component reaction

European Journal of Organic Chemistry

Volumn , Issue 9, 2010, Pages 1772-1777

  Trofimov, Boris A ^a   Andriyankova, Ludmila V ^a   Belyaeva, Kseniya V ^a   Mal'Kina, Anastasiya G ^a   Nikitina, Lina P ^a   Afonin, Andrei V ^a   Ushakov, IgoR'A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

Aldehydes, multicomponent reactions; Alkynes; Electron deficient compounds; Nitrogen heterocycles

Indexed keywords

EID: 77949292731     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901397     Document Type: Article

References (29)

1. a) M. R. Grimmett in Comprehensive Heterocyclic Chemistry II (Eds.: A. R. Katrizky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, vol.3, pp. 77-220;
2. b) C. A. Zificsak, D. J. Hlasta, Tetrahedron 2004, 60, 8991-9016;
3. c) A. Puratchikody, M. Doble, Bioorg. Med. Chem. 2007, 15, 1083-1090;
4. d) F. Bellina, S. Cauteruccio, R. Rossi, Tetrahedron 2007, 63, 4571-4624;
5. e) S. Sharma, S. Gangal, A. Rauf, Eur. J. Med. Chem. 2009, 44, 1751-1757.
6. a) B. Iddon, Heterocycles 1985, 23, 417-443;
7. b) B. Iddon, R. I. Ngochindo, Heterocycles 1994, 38, 2487-2568;
8. c) P. Merino, Prog. Heterocycl. Chem. 1999, 11, 21-42.
9. D. I Brauer, K. W Kottsieper, C. Liek, O. Stelzer, H. Waffenschmidt, P. Wasserscheid, J. Organomet. Chem. 2001, 630, 177-184.
10. S. K. Sharma, M. Tandon, J. W. Lown, J. Org. Chem. 2000, 65, 1102-1107.
11. a) D. J. Hlasta, Org. Lett. 2001, 3, 157-159;
12. b) Y. Deng, D. J. Hlasta, Org. Lett. 2002, 4, 4017-4020;
13. c) Y. Deng, D. J. Hlasta, Tetrahedron Lett. 2002, 43, 189-192;
14. d) C. Zificsak, D. J. Hlasta, Tetrahedron Lett. 2005, 46, 4789-4792.
15. a) S. Pivsa-Art, T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1998, 71, 467-473;
16. b) M. Ababri, F. Dehmel, P. Knochel, Tetrahedron Lett. 1999, 40, 7449-7453;
17. c) F. Bellina, C. Calandri, S. Cauteruccio, R. Rossi, Tetraliedron 2007, 63, 1970-1980.
18. Y. Fukumoto, K. Sawada, M. Hagihara, N. Chatani, S. Murai, Angew. Chem. Int. Ed. 2002, 41, 2779-2781.
19. a) V. Nair, S. Bindu, V. Sreekumar, N. P. Rath, Org. Lett. 2003, 5, 665-667;
20. b) V Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, L. Balagopal, Acc. Chem. Res. 2003, 36, 899-907;
21. c) V. Nair, S. Bindu, V. Sreekumar, Angew. Chem. Int. Ed. 2004, 43, 5130-5135;
22. d) V Nair, R. S. Menon, V. Sreekumar, Pure Appl. Chem. 2005, 77, 1191-1198;
23. e) V. Nair, V. Sreekumar, S. Bindu, E. Suresh, Org. Lett. 2005, 7, 2297-2300.
24. a) B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal'kina, L. P. Nikitina, A. V. Afonin, I. A. Ushakov, J. Org. Chem. 2008, 73, 9155-9157;
25. b) B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. .Mal'kina, L. P. Nikitina, Izv. Akad. Nauk Ser. Khim. 2008, 2191-2192;
26. c) B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal'kina, L. P. Nikitina, A. V. Afonin, I. A. Ushakov, Mendeleev Commun. 2009, 19, 4244.
27. Yu. M. Skvortsov, A. G. Mal'kina, A. N. Volkov, B. A. Trofimov, E. B. Oleinikova, I. V. Kazin, V. V. Gedymin, Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 872-875.
28. B. A. Trofimov, Heteroatomic Derivatives of Acetylene: New Polyfunctional Monomers, Reagents, and Intermediates, Nauka, Moscow, 1981, 320 p. (in Russian).
29. O. V. Starikova, G. V. Dolgushin, L. I. Larina, T. N. Komarova, V. A. Lopyrev, Arkivoc 2003, 13, 119-124.