The first synthesis of 2-amino-1,4-dihydroquinolines

Tetrahedron

Volumn 65, Issue 49, 2009, Pages 10149-10154

  Viault, Guillaume ^a   Grée, Danielle ^a   Roisnel, Thierry ^b   Chandrasekhar, Srivari ^c   Grée, René ^a  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,4 Dihydroquinolines; Anti cancer; Bcl 2; Benzopyran; HA 14 1

Indexed keywords

ACETIC ACID DERIVATIVE; BENZALDEHYDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIHYDROQUINOLINE DERIVATIVE; ETHYL 2 (ACETYLIMINO) 1 BENZOYL 6 BROMO 1,2 DIHYDROQUINOLINE 3 CARBOXYLATE; ETHYL 2 (ACETYLIMINO) 1 BENZYL 6 BROMO 1,2 DIHYDROQUINOLINE 3 CARBOXYLATE; ETHYL 2 AMINO 1 BENZOYL 6 BROMO 4 PHENYL 1,4 DIHYDROQUINOLINE 3 CARBOXYLATE; ETHYL 2 AMINO 1 BENZYL 6 BROMO 4 PHENYL 1,4 DIHYDROQUINOLINE 3 CARBOXYLATE; ETHYL 2 AMINO 1 BENZYL 6 BROMO 4 STYRYL 1,4 DIHYDROQUINOLINE 3 CARBOXYLATE; ETHYL 2 AMINO 1 BENZYL 6 BROMO 4 VINYL 1,4 DIHYDROQUINOLINE 3 CARBOXYLATE; ETHYLCYANOACETATE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; POLYMERIZATION; PRIORITY JOURNAL;

EID: 70350491207     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.018     Document Type: Article

References (38)

1. See for instance:
2. Khafagy M.M., El-Wahas A.H.F.A., Eid F.A., and El-Agrody A.M. Il Fármaco 57 (2002) 715-722
3. Kidwai M., Saxena S., Khan M.K.R., and Thukral S.S. Bioorg. Med. Chem. Lett. 15 (2005) 4295-4298
4. Makarem S., Mohammadi A.A., and Fakhari A.R. Tetrahedron Lett. 49 (2008) 7194-7196
5. Elinson M.N., Dorofeev A.S., Miloserdov F.M., Ilovaisky A.I., Feducovich S.K., Belyakov P.A., and Nikishin G.I. Adv. Synth. Catal. 350 (2008) 591-601 and references cited therein
6. Wang J.-L., Liu D., Zhang Z.-J., Shan S., Han X., Srinivasula S.M., Croce C.M., Alnemri E.S., and Huang Z. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 7124-7129
7. Skommer J., Wlodkowic D., Matto M., Eray M., and Pelkonen J. Leuk. Res. 30 (2006) 322-331
8. Doshi J.M., Tian D., and Xing C. J. Med. Chem. 49 (2006) 7731-7739
9. Doshi J.M., Tian D., and Xing C. Mol. Pharm. 4 (2007) 919-928 and references cited therein
10. Kemnitzer W., Drewe J., Jiang S., Zhang H., Wang Y., Zhao J., Jia S., Herich J., Labreque D., Storer R., Meerovitch K., Bouffard D., Rej R., Denis R., Blais C., Lamothe S., Attardo G., Gourdeau H., Tseng B., Kasibhatla S., and Cai S.X. J. Med. Chem. 47 (2004) 6299-6310
11. Kemnitzer W., Khasibhatla S., Jiang S., Zhang H., Zhao J., Jia S., Xu L., Crogan-Grundy C., Denis R., Barriault N., Vaillancourt L., Charron S., Dodd J., Attardo G., Labreque D., Lamothe S., Gourdeau H., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. Lett. 15 (2005) 4745-4751
12. Kemnitzer W., Drewe J., Jiang S., Zhang H., Wang Y., Zhao J., Crogan-Grundy C., Xu L., Lamothe S., Gourdeau H., Denis R., Tseng B., Kasibhatla S., and Cai S.X. J. Med. Chem. 50 (2007) 2858-2864
13. Kemnitzer W., Drewe J., Jiang S., Crogan-Grundy C., Labreque D., Bubenick M., Attardo G., Denis R., Lamothe S., Gourdeau H., Tseng B., Kasibhatla S., and Cai S.X. J. Med. Chem. 51 (2008) 417-423
14. Fujimoto A., and Sakurai A. Synthesis (1977) 871-872
15. Roudier J.-F., and Foucaud A. Synthesis (1984) 159-160
16. Yu N., Aramini J.M., Germann M.W., and Huang Z. Tetrahedron Lett. 41 (2000) 6993-6996
17. Ballini R., Bossica G.B., Conforti M.L., Maggi R., Maccazani A., Righi P., and Sartori G. Tetrahedron 57 (2001) 1395-1398
18. Curini M., Epifano F., Chimichi S., Montanari F., Nocchetti M., and Rosati O. Tetrahedron Lett. 46 (2005) 3497-3499
19. Curini M., Rosati O., Marcotullio M.C., Montanari F., Campagna V., Pace V., and Cravotto G. Eur. J. Org. Chem. 3 (2006) 746-751
20. Manero F., Gautier F., Gallenne T., Cauquil N., Grée D., Cartron P.-F., Geneste O., Grée R., Vallette F.M., and Juin P. Cancer Res. 66 (2006) 2757-2764
21. Oliver L., Mahé B., Grée R., Vallette F.M., and Juin P. Leuk. Res. 31 (2007) 859-863
22. Grée D., Vorin S., Manthati V.L., Caijo F., Viault G., Manero F., Juin P., and Grée R. Tetrahedron Lett. 49 (2008) 3276-3278
23. The addition of nucleophiles to quinolinium salts is a well established method for the synthesis of substituted quinolines but it gives mainly the 1,2 dihydroderivatives. For representative examples see:
24. Mani N.S., Chen P., and Jones T.K. J. Org. Chem. 64 (1999) 6911-6914
25. Diaba, Le Houerou C., Grignon-Dubois M., and Gerval P. J. Org. Chem. 65 (2000) 907-910 and references cited therein
26. Bohn P., Le Fur N., Hagues G., Costentin J., Torquet N., Papamicaël C., Marsais F., and Levacher V. Org. Biomol. Chem. 7 (2009) 2612-2618
27. Marsais, F.; Bohn, P.; Levacher, V.; Le Fur, N. PCT Int. Appl., WO, 103120, 2006.
28. Mikata Y., Mizukami K., Hayashi K., Matsumoto S., Yano S., Yamazaki N., and Ohno A. J. Org. Chem. 66 (2001) 1590-1599
29. Kim J.N., Kim H.S., Gong J.H., and Chung Y.M. Tetrahedron Lett. 42 (2001) 8341-8344
30. Zhou L., and Zhang Y. J. Chem. Soc., Perkin Trans. 1 (1998) 2899-2902
31. Zhou L., Tu S., Shi D., and Dai G. J. Chem. Res., Synop. (1998) 398-399
32. Sharma U., Ahmed S., and Boruah R.C. Tetrahedron Lett. 41 (2000) 3493-3495
33. Ukhin L.Yu., and Belov E.G. Russ. Chem. Bull. 57 (2008) 418-421
34. For a similar sequence see:. He Y., Mahmud H., Moningka R., Lovely C.J., and Dias H.V.R. Tetrahedron 62 (2006) 8755-8769
35. In a few cases with some benzopyrans derivatives, cyclization occurs also on the ester affording quinolones. Volmajer J., Toplak R., Bittner S., Leban I., and Majcen Le Marechal A. Tetrahedron Lett. 44 (2003) 2363-2366
36. The crystal structure corresponding to 1,4-dihydroquinoline 8 has been deposited at the Cambridge Crystallographica Data Centre and allocated the deposition number CCDC 739472. These data can be obtained free of charge from www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +441 223 336 033; email: deposit@cccdc.cam.ac.uk.
37. Grubbs R.H. Adv. Synth. Catal. 349 (2007) 34-40
38. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370 and references cited therein