An efficient one-pot synthesis of polyhydrobenzoacridine-1-one derivatives under microwave irradiation without catalyst

Journal of Heterocyclic Chemistry

Volumn 43, Issue 6, 2006, Pages 1621-1627

  Tu, Shujiang ^a   Jia, Runhong ^a   Jiang, Bo ^a   Zhang, Yan ^a   Zhang, Junyong ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHYLAMINE; 2 NAPHTHYLAMINE; 3,3 DIMETHYL 9 (2 CHLOROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (2 THIOPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (2,3 DIMETHOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (2,4 DICHLOROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (3 NITROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (3 NITROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (3,4 DICHLOROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (3,4 DIMETHOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (3,4 DIMETHOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (3,4 METHYLENEDIOXYLPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (3,4 METHYLENEDIOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 BROMOPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 BROMOPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 CHLOROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 CHLOROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 FLUOROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 HYDROXY 3 METHOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 HYDROXY 3 METHOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 METHOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 METHOXYPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 NITROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (4 NITROPHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (N BUTYL) 1,2,3,4,9,10 HEXAHYDROBENZ[C]ACRIDIN 1 ONE; 3,3 DIMETHYL 9 (PHENYL) 1,2,3,4,9,10 HEXAHYDROBENZ[A]ACRIDIN 1 ONE; 5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; ACRIDINE DERIVATIVE; ALDEHYDE; UNINDEXED DRUG;

ARTICLE; CATALYST; MICROWAVE IRRADIATION; ORGANIC CHEMISTRY; REACTION TIME; SYNTHESIS;

EID: 33845466129     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430629     Document Type: Article

References (22)

1. [a] B. Wysocka-Skrzela, A. Ledochowski, Roccz. Chem. 50, 127 (1976);
2. [b] A. Nasim, T. Brychcy, Mutation Research/Reviews in Genetic Toxicology. 65, 261 (1979);
3. [c] U. Thull. B. Testa, Biochem. Pharmacol, 47, 2307 (1994);
4. [d] E. Reil, M. Scoll, K. Masson and W. Oettmeier, Biochem. Soc. Trans. 22, 62 (1994);
5. [e] Y. Mandi, K. Regely, I. Ocsovszky, J. Barbe, J. P. Galy, J. Molnar, Anticaner Res., 14, 2633 (1994).
6. [2a] J. M. Khurana, G. C. Maikap, S. Mehta, Synthesis, 731, (1990);
7. [b] H. Matsumoto, T. Arai, M. Takahashi, T. Ashizawa, T. Nakano, Y. Nagai, Bull. Chem. Soc. Jpn., 56, 3009 (1983);
8. [c] T. Nakano, T. Makahashi, T. Arai, S. Seki, H. Matsumoto, Y. Nagai, Chem. Lett., 613 (1982).
9. R. Popielarz, S. K. Hu, D. C. Neckers, J. Photochem. Photobiol. A. Chem., 110, 79 (1997).
10. N. Srividya, P. Ramamurthy, P. Shanmugasundaram, V. T. Ramakrishnan, J. Org. Chem., 61, 5083 (1996).
11. E. Cortés, R. Martínez, J. G. Avila, R. A. Toscano, J. Heterocycl. Chem., 25, 895 (1988).
12. I. Lielbriedis, S. R. Trusov and E. Gudriniece, Latv. P. S. R. Zinat. Akad. Vestis, Kim. Ser., 39 (1971);
13. Chem. Abstr., 75, 35674y (1971).
14. R. Martínez, E. Cortés, R. A. Toscano, J. Heterocycl. Chem., 27, 363, (1990).
15. X. S. Wang, M. M. Zhang, Z. S. Zeng, D. Q. Shi, S. J. Tu. X. Y. Wei and Z. M. Zong, Tetrahedron Lett., 46, 7169-7173 (2005).
16. X. S. Wang, M. M. Zhang, Z. S. Zeng, D. Q. Shi, S. J. Tu, X. Y. Wei and Z. M. Zong, Arkivoc, 117-123 (2006).
17. [10a] S. J. Tu, Z. S. Lu, D. Q. Shi, C. S. Yao, Y. Gao and C. Guo, Synth. Commun., 32, 2181 (2002);
18. [b] S. J. Tu, Y. J. Feng, H. J. Ma, X. H. Liu, D. Q. Shi and Y. Gao, Chinese J. Struct. Chem., 21, 96 (2002).
19. [11a] S. J. Tu, C. B. Miao, F. Fang, Y. J. Feng, T. J. Li, Q. Y. Zhuang, X. J. Zhang, S. L. Zhu, D. Q. Shi, Bioorg. & Med. Chem. Lett., 14, 1533 (2004);
20. [b] S. J. Tu, T. J. Li, F. Shi, F. Fang, S. L. Zhu, X. Y. Wei, Z. M. Zong, Chem. Lett., 34(5), 732 (2005).
21. M. Kidwai and S. Rastogi, Heteroatom Chem., 16, 138 (2005).
22. 1 = 0.0442, wR2 = 0.0999.