Four-component synthesis of imidazolinium-fused heterocycles from Ugi-smiles couplings

Synlett

Volumn , Issue 1, 2010, Pages 153-157

  Barthelon, Anaëlle ^a   Legoff, Xavier Frédéric ^b   Kaim, Laurent El ^a   Grimaud, Laurence ^a  

^a Ecole Nationale Superieure de Techniques Avancees   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

Mercaptan; Multicomponent reaction; Thioamide; Triazine; Ugi smiles

Indexed keywords

ALDEHYDE; AMINE; CYANIDE; IMIDAZOLINE DERIVATIVE; IMIDAZOLINIUM FUSED HETEROCYCLE; NITROGEN; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ELIMINATION REACTION; STOICHIOMETRY; SYNTHESIS;

EID: 77951698279     PISSN: 09365214     EISSN: 14372096     Source Type: None    
DOI: 10.1055/s-0029-1218550     Document Type: Article

References (29)

1. (a) Jagodzinski, T. S. Chem. Rev. 2003, 103, 197.
2. (b) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.
3. (c) Narender, M.; Reddy, M. S.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Tetrahedron Lett. 2005, 46, 5953.
4. (a) Artis, D. R.; Lipton, M. A. J. Am. Chem. Soc. 1998, 120, 12200.
5. (b) Miwa, J. H.; Patel, A. K.; Vivatrat, N.; Popek, S. M.; Meyer, A. M. Org. Lett. 2001, 3, 3373.
6. (c) Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685.
7. (a) Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210.
8. (b) Charette, A. B.; Grenon, M. J. Org. Chem. 2003, 68, 5792.
9. (c) Zbruyev, O. I.; Stiasni, N.; Kappe, C. O. J. Comb. Chem. 2003, 5, 145.
10. (a) Dumestre, P.; El Kaim, L.; Grégoire, A. Chem. Commun. 1999, 775.
11. (b) Allan, V.; El Kaim, L.; Grimaud, L.; Jana, N. K. Synlett 2002, 352.
12. (c) El Kaim, L.; Grimaud, L.; Oble, J. Angew. Chem. Int. Ed. 2005, 117, 7961.
13. (d) El Kaim, L.; Grimaud, L.; Oble, J. Org. Biomol. Chem. 2006, 4, 3410.
14. (e) El Kaim, L.; Gizolme, M.; Grimaud, L. Org. Lett. 2006, 8, 5021.
15. (f) El Kaim, L.; Gageat, M.; Gaultier, L. Synlett 2007, 500.
16. (g) El Kaim, L.; Grimaud, L.; Coffinier, D. Org. Lett. 2009, 11, 995.
17. (h) El Kaim, L.; Grimaud, L.; Schultz, A. Org. Biomol. Chem. 2009, 7, 3024.
18. (i) El Kaim, L.; Grimaud, L. Moll. Divers. 2009, in press; DOI: 10.1007/ s11030-009-9175-9183
19. (a) El Kaim, L.; Gizolme, M.; Grimaud, L.; Oble, J. Org. Lett. 2006, 8, 4019.
20. (b) Barthelon, A.; Dos Santos, A.; El Kaim, L.; Grimaud, L. Tetrahedron Lett. 2008, 49, 3208.
21. (c) Barthelon, A.; El Kaim, L.; Gizolme, M.; Grimaud, L. Eur. J. Org. Chem. 2008, 35, 5974.
22. El Kaim, L.; Gizolme, M.; Grimaud, L.; Oble, J. Synlett 2007, 465.
23. For a related use of the Schollkopf isocyanide with thiocarboxylic acid, see: Heck, S.; Dömling, A. Synlett 2000, 424.
24. Daunis, J.; Jacquier, R.; Viallefont, P. Bull. Soc. Chim. Fr. 1969, 10, 3675.
25. Boger, D. L. Chem. Rev. 1986, 86, 781.
26. Akritopoulou-Zanze, I.; Wang, Y.; Zhao, H.; Djuric, S. W. Tetrahedron Lett. 2009, in press; DOI: 10.1016/ j.tetlet.2009.07.036.
27. -(11 ) The crystallographic data can be obtained free of charge under the reference CCDC 730687 at the Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/ data-request-cif).
28. For related cyclization of thioamides with the formation of fused nitrogen heterocycles, see: (a) Shibahara, F.; Kitagawa, A.; Yamaguchi, E.; Murai, T. Org. Lett. 2006, 8, 5621.
29. (b) Shibahara, F.; Yoshida, A.; Murai, T. Chem. Lett. 2008, 37, 646.