Concise synthesis of 2-amino-4(3H)-quinazolinones from simple (hetero)aromatic amines

Journal of Organic Chemistry

Volumn 73, Issue 6, 2008, Pages 2473-2475

  Zeghida, Walid ^a   Debray, Julien ^a   Chierici, Sabine ^a   Dumy, Pascal ^a   Demeunynck, Martine ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; DERIVATIVES; FRIEDEL-CRAFTS REACTION; PURIFICATION;

AROMATIC AMINES; CHROMATOGRAPHIC PURIFICATION; HETEROAROMATIC RINGS;

AROMATIC COMPOUNDS;

AROMATIC AMINE; QUINAZOLINONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; MOLECULAR DYNAMICS; PURIFICATION; SUBSTITUTION REACTION;

EID: 41849119877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7026883     Document Type: Article

References (28)

1. Pendergast, W.; Johnson, J. V.; Dickerson, S. H.; Dev, I. K.; Duch, D. S.; Ferone, R.; Hall, W. R.; Humphrey, J.; Kelly, J. M.; Wilson, D. C. J. Med. Chem. 1993, 36, 2279-2291.
2. Chem, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128-3141.
3. Grosso, J. A.; Nichols, E. D.; Kohli, J. D.; Glock, D. J. Med. Chem. 1982, 25, 703-708.
4. Somers, F.; Ouedraogo, R.; Antoine, M.-H.; de Tullio, P.; Becker, B.; Fontaine, J.; Damas, J.; Dupont, L.; Rigo, B.; Delarge, J.; Lebrun, P.; Pirotte, B. J. Med. Chem. 2001, 44, 2575-2585.
5. Alagarsamy, V.; Dhanabal, K.; Parthiban, P.; Anjana, G.; Deepa, G.; Murugesan, B.; Rajkumar, S.; Beevi, A. J. J. Pharm. Pharmacol. 2007, 59, 669-677.
6. (a) Leonard, N. J. Acc. Chem. Res. 1982, 15, 128-135.
7. (b) Keyser, G. E.; Leonard, N. J. J. Org. Chem. 1976, 41, 3529-3532.
8. Liu, H.; Gao, J.; Kool, E. T. J. Org. Chem. 2005, 70, 639-647.
9. (a) For a recent review, see: Vögtle, M. M.; Marzinzik, A. L. QSAR Comb. Sci. 2004, 23, 440-459.
10. See also: (b) Kundu, B.; Partani, P.; Duggineni, S.; Sawant, D. J. Comb. Chem. 2005, 7, 909-915.
11. (c) Wéber, C.; Demeter, A.; Szendrei, G. I.; Greiner, I. Tetrahedron Lett. 2003, 44, 7533-7536.
12. (d) Yang, R.-Y.; Kaplan, A. Tetrahedron Lett. 2000, 41, 7005-7008.
13. (e) Gopalsamy, A.; Yang, H. J. Comb. Chem. 2000, 2, 378-381.
14. (f) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 5831-5834.
15. (g) Wilson, L. J. Org. Lett. 2001, 3, 585-588.
16. (h) Villalgordo, J. M.; Obrecht, D.; Chucholowsky, A. Synlett 1998, 1405-1407.
17. (i) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron 1989, 45, 4263-4286.
18. (j) Zhang, W.; Mayer, J. P.; Hall, S. E.; Weigel, J. A. J. Comb. Chem. 2001, 3, 255-256.
19. Larksarp, C.; Alper, H. J. Org. Chem. 2000, 65, 2773-2777.
20. Fray, M. J.; Mathias, J. P.; Nichols, C. L.; Po-Ba, Y. M.; Snow, H. Tetrahedron Lett. 2006, 47, 6365-6368.
21. (a) Fixler, N.; Demeunynck, M.; Duflos, A.; Lhomme, J. Heterocycles 1998, 48, 755-767.
22. (b) Charmantray, F.; Duflos, A.; Lhomme, J.; Demeunynck, M. J. Chem. Soc., Perkin Trans.1 2001, 2962-2968.
23. (c) Tatibouët, A.; Demeunynck, M.; Andraud, C.; Collet, A.; Lhomme, J. Chem. Commun. 1999, 161-162.
24. Manimala, J. C.; Anslyn, E. V. Tetrahedron Lett. 2002, 43, 565-567.
25. The synthesis and reactivity of compound 2 and other acridine analogues will be described elsewhere. The spectroscopic data of compounds 2 and 3 are given in the Supporting Information.
26. Zeghida, W. Ph.D. thesis, Université Joseph Fourier, Grenoble, France, 2007.
27. Cudero, J.; Pardo, C.; Ramos, M.; Gutierrez-Puebla, E.; Monge, A.; Elguero, J. Tetrahedron 1997, 53, 2233-2240.
28. 2O). No attempt of separation was made as the mixture was well characterized and quantified by NMR.