A novel, one-pot, three-component synthesis of 5H-[1,3]thiazolo[3,2-a] pyrimidine derivatives

Synlett

Volumn , Issue 17, 2007, Pages 2703-2706

  Adib, Mehdi ^a   Nosrati, Meisam ^a   Mahdavi, Mohammad ^a   Zhu, Long Guan ^b   Mirzaei, Peiman ^c  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ZHEJIANG UNIVERSITY   (China)

^c SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

5H 1,3 thiazolo 3,2 a pyrimidines; Cyclizations; Heterocycles; Isocyanides; Three component reaction

Indexed keywords

ACETIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; DI TERT BUTYL 7 [CYCLO HEXYL(2 ETHOXY 2 OXO ACETYL)AMINO] 3 METHYL 5H [1,3]THIAZOLO[3,2 A]PYRIMIDINE 5,6 DICARBOXYLATE; DIETHYL 7 [TERT BUTYL(2 ETHOXY 2 ACETYL)AMINO] 3 METHYL 5H [1,3]THIAZOLO[3,2 A]PYRIMIDINE 5,6 DICARBOXYLATE; DIMETHYL 7 [CYCLOHEXYL(2 ETHOXY 2 OXOACETYL)AMINO] 5H [1,3}THIAZOLO[3,2 A]PYRIMIDINE 5,6 DICARBOXYLATE; DIMETHYL 7 [TERT BUTYL(2 ETHOXY 2 OXOACETHYL)AMINO] 5H [1,3]THIAZOLO[3,2 A]PYRIMIDINE 5,6 DICARBOXYLATE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; ONE POT SYNTHESIS;

EID: 35748975966     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991048     Document Type: Article

References (31)

1. (a) Bagley, M. C.; Dale, J. W.; Bower, J. Chem. Commun. 2002, 1682.
2. (b) Mont, N.; Teixidó, J.; Borrell, J. I.; Kappe, C. O. Tetrahedron Lett. 2003, 44, 5385.
3. (c) Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957.
4. (d) Cui, S. L.; Lin, X. F.; Wang, Y. G. J. Org. Chem. 2005, 70, 2866.
5. (e) Huang, Y. J.; Yang, F. Y.; Zhu, C. J. J. Am. Chem. Soc. 2005, 127, 16386.
6. (f) Ramon, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602.
7. (g) Dömling, A. Chem. Rev. 2006, 106, 17.
8. (h) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
9. Tozkoparan, B.; Ertan, M.; Kelicen, P.; Demirdamar, R. Farmaco 1999, 30, 588.
10. Jeanneau-Nicolle, E.; Benoit-Guyod, M.; Namil, A.; Leclerc, G. Eur. J. Med. Chem. 1992, 27, 115.
11. Sayed, H. H.; Shamroukh, A. H.; Rashad, A. E. Acta Pharm. 2006, 56, 231.
12. Coburn, R. A.; Glennon, R. A. J. Pharm. Sci. 1973, 62, 1785.
13. Nobe, K.; Miyatake, M.; Nobe, H.; Sakai, Y.; Takashima, J.; Momose, K. Brit. J. Pharmacol. 2004, 143, 166.
14. Balkan, A.; Uma, S.; Ertan, M.; Wiegrebe, W. Pharmazie 1992, 47, 687.
15. Wichmann, J.; Adam, G.; Kolczewski, S.; Mutel, V.; Woltering, T. Bioorg. Med. Chem. Lett. 1999, 9, 1573.
16. Proudfoot, J. R. Expert Opin. Ther. Pat. 1998, 8, 971.
17. (a) Elokhina, V. N.; Nakhmanovich, A. S.; Stepanova, Z. V.; Lopyrev, V. A.; Bannikova, O. B.; Struchkov, Y. T.; Shishkin, O. V. Russ. Chem. Bull. 1996, 45, 2189.
18. (b) Sherif, S. M.; Youssef, M. M.; Mobarak, K. M.; Abdel-Fattah, A.-S. M. Tetrahedron 1993, 49, 9561.
19. (c) Liu, Y. S.; Huang, W. Y. J. Chem. Soc. Perkin Trans. 1 1997, 981.
20. (d) Katritzky, A. R.; Rogers, J. W.; Witek, R. M.; Nair, S. K. ARKIVOC 2004, (viii), 52.
21. (e) Ye, F. C.; Chen, B. C.; Huang, X. Synthesis 1989, 317.
22. (f) Landreau, C.; Deniaud, D.; Reliquet, A.; Meslin, J. C. Synthesis 2001, 2015.
23. (g) Hurst, D. T.; Beaumont, C.; Jones, D. T. E.; Kingsley, D. A.; Patridge, J. D.; Rutherford, T. J. Aust. J. Chem. 1988, 41, 1209.
24. (h) Liebscher, J.; Hassoun, A. Synthesis 1988, 816.
25. 2 (2 mL) at 25°C over 10 min. The reaction mixture was then stirred for 24 h. The solvent was removed and the residue was purified by column chromatography using n-hexane-EtOAc (1:2) as eluent. The solvent was removed and the product was obtained. Yield: 0.41 g (90%); yellow crystals. IR (KBr):(...)
26. 1 = 0.062. CCDC 640870 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
27. (a) Nair, V.; Vinod, A. U.; Nair, J. S.; Sreekanth, A. R.; Rath, N. P. Tetrahedron Lett. 2000, 41, 6675.
28. (b) Nair, V.; Deepthi, A. Tetrahedron Lett. 2006, 47, 2037.
29. Walborsky, H. M.; Periasamy, M. P. In The Chemistry of Functional Groups, Supplement C; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1983, Chap. 20, 835-837.
30. Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810.
31. Ugi, I. Isonitrile Chemistry; Academic Press: London, 1971.