Synthesis of polysubstituted 5-aminopyrimidines from α-azidovinyl ketones and amidines

Tetrahedron

Volumn 67, Issue 14, 2011, Pages 2676-2680

  Hu, Miao ^a   Wu, Jianwei ^a   Zhang, Yaohong ^a   Qiu, Fangli ^a   Yu, Yongping ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

1, 4 Michael addition; Amidines; Polysubstituted 5 aminopyrimidines; Rearrangement; azidovinyl ketones

Indexed keywords

4 (2 BROMOPHENYL) 6 (4 METHOXYPHENYL)PYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 2 METHYL 6 (4 TOLYL)PYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 2 METHYL 6 PHENYLPYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 2 PHENYL 6 (4 TOLYL)PYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 2,6 DIPHENYLPYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 6 (4 CHLOROPHENYL) 2 METHYLPYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 6 (4 CHLOROPHENYL) 2 PHENYLPYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 6 (4 CHLOROPHENYL)PYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 6 (4 TOLYL)PYRIMIDIN 5 AMINE; 4 (4 BROMOPHENYL) 6 PHENYLPYRIMIDIN 5 AMINE; 4 (4 CHLOROPHENYL) 6 (4 METHOXYPHENYL)PYRIMIDIN 5 AMINE; 4 (4 CHLOROPHENYL) 6 (THIOPHEN 2 YL)PYRIMIDIN 5 AMINE; 4 (4 FLUOROPHENYL) 2 METHYL 6 (THIOPHEN 2 YL)PYRIMIDIN 5 AMINE; 4 (4 METHOXYPHENYL) 2 METHYL 6 (4 NITROPHENYL)PYRIMIDIN 5 AMINE; 4 (4 METHOXYPHENYL) 6 (4 NITROPHENYL) 2 PHENYLPYRIMIDIN 5 AMINE; 4 (4 METHOXYPHENYL) 6 (THIOPHEN 2 YL)PYRIMIDIN 5 AMINE; 4 (4 METHOXYPHENYL) 6 PHENYLPYRIMIDIN 5 AMINE; 5 AMINOPYRIMIDINE DERIVATIVE; ALPHA AZIDOVINYL KETONE; AMIDINE; KETONE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICHAEL ADDITION; PRIORITY JOURNAL; SYNTHESIS;

EID: 79952573178     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.01.062     Document Type: Article

References (32)

1. Brown, D. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C.W., Eds.; Pergamon: Oxford, 1996; Vol. 3, Chapter 2.13.
2. Lagoja, I. M. Chem. Biodiversity 2005, 2, 1.
3. Thompson, M. D.; Cupps, T. L.; Wise, D. S.; Wotring, L. L.; Townsend, L. B. J. Med. Chem. 1997, 40, 766.
4. Provins, L.; Christophe, B.; Danhaive, P.; Dulieu, J.; Durieu, V.; Gillard, M.; Lebon, F.; Lengele, S.; Quere, L.; van Keulen, B. Bioorg. Med. Chem. Lett. 2006, 16, 1834.
5. Zhang, H.; Schinazi, R. F.; Chu, C. K. Bioorg. Med. Chem. 2006, 14, 8314.
6. Otmar, M.; Masojidkova, M.; Votruba, I.; Holy, A. Bioorg. Med. Chem. 2004, 12, 3187.
7. Chae, M. Y.; Swenn, K.; Kanugula, S.; Dolan, M. E.; Pegg, A. E.; Moschel, R. C. J. Med. Chem. 1995, 38, 359.
8. (a) Gompper, R.; Mair, H. J.; Polborn, K. Synthesis 1997, 696;
9. (b) Kanbara, T.; Kushida, N.; Saito, I.; Kuwajima, K. K.; Yamamoto, T. Chem. Lett. 1992, 21, 583.
10. (a) Hanan, G. S.; Vilkmer, D.; Schubert, U. S.; Lehn, J. M.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. 1997, 36, 1842;
11. (b) Bassani, D. M.; Lehn, J. M.; Baum, C.; Fenske, D. Angew. Chem., Int. Ed. 1997, 36, 1845;
12. (c) Semenov, A.; Spatz, J. P.; M€oller, M.; Lehn, J. M.; Schubert, D.; Weidl, C. H.; Schubert, U. S. Angew. Chem., Int. Ed. 1999, 38, 2547.
13. Kuno, A.; Sugiyama, Y.; Katsuta, K.; Kamitani, T.; Takasugi, H. Chem. Pharm. Bull. 1992, 40, 1452.
14. Carsten, J. WO Patent 0,097,379, 2010; Chem. Abstr. 2010, 153, 359052.
15. Müller, T. J.; Braum, R.; Ansorge, M. Org. Lett. 2000, 2, 1967.
16. (a) Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125;
17. (b) Turck, A.; Pré, N.; Leprêtre-Gaquère, G.; Quéguiner, G. Heterocycles 1998, 49, 205.
18. (a) Zapol'kii, V. A.; Namyslo, J. C.; Altug, C.; Gjikaj, M.; Kaufmann, D. E. Synthesis 2008, 304;
19. (b) Kaname, T.; Masaaki, T.; Yukitoshi, M.; Kuniyoshi, O.; Katsuyuki, I.; Hikari, M.; Tomoji, A. J. Heterocycl. Chem. 1987, 24, 1003;
20. (c) Masaaki, T.; Yukitoshi, M.; Hikari, M.; Kaname, T. Chem. Pharm. Bull. 1985, 33, 2129.
21. (a) Khanzhin, N. U.S. Patent 7,066,612, 2007; Chem. Abstr. 2007, 146, 337905;
22. (b) Davey, D.D. EP Patent 1,429,149, 1991; Chem. Abstr. 1991, 115, 183357.
23. (a) L'abbé, G.; Mathys, G. J. Org. Chem. 1974, 39, 1778;
24. (b) L'abbé, G.; Mathys, G.; Toppet, S. J. Org. Chem. 1975, 40, 1975.
25. (a) Chiba, S.; Wang, Y. F.; Lapointe, G.; Narasaka, K. Org. Lett. 2008, 10, 313;
26. (b) Wang, Y. F.; Toh, K. K.; Chiba, S.; Narasaka, K. Org. Lett. 2008, 10, 5019;
27. (c) Wang, Y. F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570.
28. Yang, Y. Y.; Shou, W. G.; Chen, Z. B.; Hong, D.; Wang, Y. G. J. Org. Chem. 2008, 73, 3928.
29. Chen, W. C.; Hu, M.; Wu, J. W.; Zou, H. B.; Yu, Y. P. Org. Lett. 2010, 12, 3863.
30. Knittel, D.; Hemetsberger, H.; Weidmann, H. Monatsh. Chem. 1970, 101, 157.
31. Gilchrist, T. L.; Mendonca, R. ARKIVOC 2000, 769.
32. Patonay, T.; Jekocombining double grave accent, J.; Rimán, E. Synth. Commun. 2002, 32, 2403.