An improved synthesis of reduced 9-arylacridine-1,8-diones from 3-amino-5,5-dimethylcyclohex-2-enone, arylaldehydes and 1,3-dicarbonyl compounds in aqueous medium

Journal of Chemical Research

Volumn , Issue 11, 2006, Pages 719-721

  Wang, Xiang Shan ^a,b,c   Zhang, Mei Mei ^a   Shi, Da Qing ^a,c   Tu, Shu Jiang ^a,c   Wei, Xian Yong ^b   Zong, Zhi Min ^b  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b CHINA UNIVERSITY OF MINING AND TECHNOLOGY   (China)

^c JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Acridine 1,8 diones; Aldehydes; PTC; Reactions in water; TBAC

Indexed keywords

EID: 33845943684     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823406779173352     Document Type: Article

References (25)

1. R.A. Janis, P.J. Silver and D.J. Triggle, Adv. Drug. Res. 1987, 16, 309;
2. (b) R. Shan, C. Velazquez and E.E. Knaus, J. Med. Chem. 2004, 41, 254;
3. (c) A.F. Dulhunty, S.M. Curtis, S. Watson, L. Cengia and G. Marco, J. Biol. Chem. 2004, 279, 11853.
4. N. Martin, M. Quinteiro, C. Seoane, L. Mora, M. Suarez, E. Ochoa and A. Morales, J. Heterocycl. Chem. 1995, 51, 235.
5. X.S. Wang, M.M. Zhang, Z.S. Zeng, D.Q. Shi, S.J. Tu, X.Y. Wei and Z.M. Zong, Tetrahedron Lett. 2005, 46, 7169;
6. (b) X.S. Wang, D.Q. Shi, Y.F. Zhang, S.H. Wang and S.J. Tu, Chin. J. Org. Chem. 2004, 24, 430.
7. S.J. Tu, C.B. Miao, Y. Gao, Y.J. Feng and J.C. Feng, Chin. J. Chem. 2002, 20, 703.
8. Y.L. Li, M.M. Zhang, X.S. Wang, D.Q. Shi, S.J. Tu, X.Y. Wei and Z.M. Zong, J. Chem. Res. 2005, 600.
9. Y. Mikata, M. Yokoyama, K. Mogami, M. Kato, I. Okura, M. Chikira and S. Yano, Inorg. Chim. Acta, 1998, 279, 51.
10. Antonini, P. Polucci, L.R. Kelland, E. Menta, N. Pescalli and S. Martelli, J. Med. Chem., 1999, 42, 2535.
11. S.A. Gamage, J.A. Spicer, G.J. Atwell, G.J. Finlay, B.C. Baguley and W.A. Denny, J. Med. Chem. 1999, 42, 2383.
12. N.M. Eid, H.M. Safwat, M.A. Ramadan, S.A. Shouman and A.A. El-Esawy, Bull. Fac. Pharm. 1995, 33, 25.
13. S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K.M.J. Wolfart and J. Barbe, Eur. J. Med. Chem. 2003, 38, 19.
14. Srivastava and C. Nizamuddin, Indian J. Heterocycl. Chem. 2004, 13, 261.
15. L. Ferencz and M. Peter, Farmacia 2003, 51, 52.
16. R. Breslow and D.C. Rideout, J. Am. Chem. Soc. 1980, 102, 7816;
17. (b) R. Breslow, Acc. Chem. Res. 1991, 24, 159.
18. A.A. Ponaras, J. Org. Chem. 1983, 48, 3866;
19. (b) R.M. Coates, B.D. Rogers, S.J. Hobbs, D.R. Peck and D.P. Curran, J. Am. Chem. Soc. 1987, 109, 1160;
20. (c) H. Mattes and C. Benezra, Tetrahedron Lett. 1985, 26, 5697;
21. (d) J.Y. Zhou, G.D. Lu and S.H. Wu, Synth. Commun. 1992, 22, 481;
22. (e) P. Delair and J. L. Luche, J. Chem. Soc., Chem. Commun. 1989, 398;
23. (f) X.S. Wang, M.M. Zhang, Z.S. Zeng, D.Q. Shi, S.J. Tu, X.Y. Wei and Z.M. Zong, Chem. Lett. 2005, 34, 1316;
24. (g) X.S. Wang, Z.S. Zeng, M.M Zhang, Y.L. Li, D.Q. Shi, S.J. Tu, X.Y. Wei and Z.M. Zong, J. Chem. Res. 2006, 228.
25. P.G. Baraldi, D. Simoni and S. Manfredini, Synthesis, 1980, 902.