A cascade reaction with iminium ion isomerization as the key step leading to tetrahydropyrimido[4,5-d]pyrimidines

Organic Letters

Volumn 10, Issue 5, 2008, Pages 889-892

  Zheng, Lianyou ^a   Yang, Fengzhi ^a   Dang, Qun ^a   Bai, Xu ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; IMINES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRIMIDINES; STEREOISOMERISM;

EID: 43549110570     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol703049j     Document Type: Article

References (29)

1. For examples, see: (a) Wang, S.; Folkes, A.; Chuckowree, I.; Cockcroft, X.; Sohal, S.; Miller, W.; Milton, J.; Wren, S. P.; Vicker, N.; Depledge, P.; Scott, J.; Smith, L.; Jones, H.; Mistry, P.; Faint, R.; Thompson, D.; Cocks, S. J. Med. Chem. 2004, 47, 1329-1338.
2. (b) Perner, R. J.; Gu, Y. G.; Lee, C. H.; Bayburt, E. K.; McKie, J.; Alexander, K. M.; Kohlhaas, K. L.; Wismer, C. T.; Mikusa, J.; Jarvis, M. F.; Kowaluk, E. A.; Bhagwat, S. S. J. Med. Chem. 2003, 46, 5249-5257.
3. (c) McGuigan, C.; Pathirana, R. N.; Snoeck, R.; Andrei, G.; DeClercq, E.; Balzarini, J. J. Med. Chem. 2004, 47, 1847-1851.
4. (d) Gangjee, A.; Zeng, Y.; McGuire, J. J.; Mehraein, F.; Kisliuk, R. L. J. Med. Chem. 2004, 47, 6893-6901.
5. (a) Yang, J.; Che, X.; Dang, Q.; Wei, Z.; Gao, S.; Bai, X. Org. Lett. 2005, 7, 1541-1543.
6. (b) Fu, R.; Xu, X.; Dang, Q.; Bai, X. J. Org. Chem. 2005, 70, 10810-10816.
7. (c) Che, X.; Zheng, L.; Dang, Q.; Bai, X. Tetrahedron 2006, 62, 2563-2568.
8. (d) Xiang, J.; Zheng, L.; Chen, F.; Dang, Q.; Bai, X. Org. Lett. 2007, 9, 765-767.
9. (a) Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765-2809.
10. (b) Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484-4517.
11. Gomtsyan, A.; Didomenico, S.; Lee, C. H.; Matulenko, M. A.; Kim, K.; Kowaluk, E. A.; Wismer, C. T.; Mikusa, J.; Yu, H.; Kohlhaas, K.; Jarvis, M. F.; Bhagwat, S. S. J. Med. Chem. 2002, 45, 3639-3648.
12. Clark, J.; Parvizi, B.; Southon, I. W. J. Chem. Soc., Perkin Trans. 1 1976, 125-130.
13. Curtin, N. J.; Barlow, H. C.; Bowman, K. J.; Calvert, A. H.; Davison, R.; Golding, B. T.; Huang, B.; Loughlin, P. J.; Newell, D. R.; Smith, P. G.; Griffin, R. J. J. Med. Chem. 2004, 47, 4905-4922.
14. Sanghvi, Y. S.; Larson, S. B.; Matsumoto, S. S.; Nord, L. D.; Smee, D. F.; Willis, R. C.; Avery, T. H.; Robins, R. K.; Revankar, G. R. J. Med. Chem. 1989, 32, 629-637.
15. Gebauer, M. G.; McKinlay, C.; Gready, J. E. Eur. J. Med. Chem. 2003, 38, 719-728.
16. Ram, V. J.; Goel, A.; Sarkhel, S.; Maulik, P. R. Bioorg. Med. Chem. 2002, 10, 1275-1280.
17. (a) Dabiri, M.; Arvin-Nezhad, H.; Khavasi, H. R.; Bazgir, A. Tetrahedron 2007, 63, 1770-1774.
18. (b) Prajapati, D.; Gohain, M.; Thakur, A. J. Bioorg. Med. Chem. Lett. 2006, 16, 3537-3540.
19. (c) Sharma, P.; Kumar, A.; Rane, N.; Gurram. V. Tetrahedron 2005, 61, 4237-4248.
20. (d) Prajapati, D.; Thakur, A. J. Tetrahedron Lett. 2005, 46, 1433-1436.
21. (e) Sharma, P.; Rane, N.; Gurram, V. K. Bioorg. Med. Chem. Lett. 2004, 14, 4185-4190.
22. (f) Devi, I.; Borah, H. N.; Bhuyan, P. J. Tetrahedron Lett. 2004, 45, 2405-2408.
23. (g) Gebauer, M. G.; McKinlay, C.; Gready, J. E. Eur. J. Med. Chem. 2003, 38, 719-728.
24. (h) Srivastava, S. K.; Haq, W.; Chauhan, P. M. S. Bioorg. Med. Chem. Lett. 1999, 9, 965-966.
25. (i) Graveleau, N.; Masquelin, T. Synthesis 2003, 11, 1739-1743.
26. (a) Wang, Z. J.; Neidlein, R. Tetrahedron 1998, 54, 9903-9910.
27. (b) Burch, H. A.; Benjamin, L. E. J. Med. Chem. 1974, 17, 451-453.
28. Harmon, R. A.; Parsons, J. L.; Gupta, S. K. J. Org. Chem. 1969, 34, 2760-2762.
29. Liu, J.; Dang, Q.; Wei, Z.; Zhang, H.; Bai, X. J. Comb. Chem. 2005, 7, 627-636.