A novel and efficient synthesis of 1-hydroxyquinazolin-4-ones via tin(II) chloride induced cyclization of 2-nitrobenzamides and ketones

Synthesis

Volumn , Issue 13, 2008, Pages 2000-2006

  Shi, Daqing ^a,b   Dou, Guolan ^b   Zhou, Yao ^b  

^a SOOCHOW UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

1 hydroxyquinazolin 4 one; 2 nitrobenzamide; Ketone; Tin(II) chloride dehydrate

Indexed keywords

CYCLIZATION; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL); TIN; TITANIUM COMPOUNDS;

2 NITROBENZAMIDES; DIHYDRATE; EFFICIENT SYNTHESIS; SHORT REACTION TIMES; STARTING MATERIALS; TIN(IV) CHLORIDE;

KETONES;

1 HYDROXYQUINAZOLIN 4 ONE; 2 NITROBENZAMIDE; BENZAMIDE DERIVATIVE; KETONE DERIVATIVE; QUINAZOLINE DERIVATIVE; TIN CHLORIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS; X RAY DIFFRACTION;

EID: 47349124263     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067126     Document Type: Article

References (20)

1. (a) Chan, J. H.; Hong, J. S.; Kuyper, L. F.; Jones, M. L.; Baccanari, D. P.; Tansik, R. L.; Boytos, C. M.; Rudolph, S. K.; Brown, A. D. J. Heterocycl. Chem. 1997, 34, 145.
2. (b) Gackenheimer, S. L.; Schaus, J. M.; Gehlert, D. R. J. Pharmacol. Exp. Ther. 1996, 732, 113.
3. (c) Dempcy, R. Q.; Skibo, E. B. Biochemistry 1991, 30, 8480.
4. (d) Campbell, S. F.; Davey, M. J. Drug Design Delivery 1986, 83.
5. (e) Imagawa, J.; Sakai, K. Eur. J. Pharmacol. 1986, 131, 257.
6. Hasegawa, H.; Muraoka, M.; Matsui, K.; Kojima, A. Bioorg. Med. Chem. Lett. 2003, 13, 3471.
7. (a) Ried, W.; Sinharray, A. Chem. Ber. 1963, 96, 3306.
8. (b) Jiang, J. B.; Hesson, D. P.; Dusak, B. A.; Dexter, D. L.; Kang, G. L.; Hamel, E. J. Med. Chem. 1990, 33, 1721.
9. (c) Connolly, D. J.; Guiry, P. J. Synlett 2001, 1707.
10. Connoly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153.
11. (a) Schlapbach, A.; Heng, R.; Padova, F. D. Bioorg. Med. Chem. Lett. 2004, 14, 357.
12. (b) Ferraccioli, R.; Carenzi, D. Synthesis 2003, 1383.
13. (a) Takeuchi, H.; Haguvara, S.; Eguchi, S. Tetrahedron 1989, 45, 6375.
14. (b) Takeuchi, H.; Matsushita, Y.; Eguchi, S. J. Org. Chem. 1991, 56, 1535.
15. (c) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1988, 29, 3849.
16. Shi, D. Q.; Rong, L. C.; Wang, J. X.; Zhuang, Q. Y.; Wang, X. S.; Hu, H. W. Tetrahedron Lett. 2003, 44, 3199.
17. Shi, D. Q.; Wang, J. X.; Shi, C. L.; Rong, L. C.; Zhuang, Q. Y.; Hu, H. W. Synlett 2004, 1098.
18. Yamaguchi, K. Bull. Chem. Soc. Jpn. 1976, 49, 1366.
19. Sam, J.; Richmond, C. W. J. Heterocycl. Chem. 1964, 1, 245.
20. Crystallographic data for the structures of 3a (CCDC-682915), 5b (CCDC-682916), 7e (CCDC-682917), and 9a (CCDC-682918) have been deposited at the Cambridge Crystallographic Data Centre. Copies of available material can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; email: deposit@ccdc.cam.ac.uk].