Facile synthesis of tricyclic oxazino- or oxazepino-fused tetrahydroquinolines via intramolecular reductive amidation

Synthesis

Volumn , Issue 13, 2011, Pages 2079-2084

  Mondal, Shyamal ^a   Maity, Arindam ^a   Naskar, Subhendu ^a   Paira, Rupankar ^a   Hazra, Abhijit ^a   Sahu, Krishnendu B ^a   Saha, Pritam ^a   Das, Saktipada ^a   Banerjee, Sukdeb ^a   Mondal, Nirup B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

(8 quinolyloxy)alkyl ester; fused tetrahydroquinoline; intramolecular amidation; reductive amidation; zinc

Indexed keywords

ALKYL ESTERS; AMIDATION; FACILE SYNTHESIS; FUSED TETRAHYDROQUINOLINE; REDUCTIVE CYCLIZATION; SHORT REACTION TIME;

ACETIC ACID; ESTERIFICATION; ESTERS; SYNTHESIS (CHEMICAL); ZINC;

CYCLIZATION;

2 METHYL 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 2,3,7,8 TETRAHYDRO 4H,6H [1,4]OXAZEPINO[2,3,4 IJ]QUINOLIN 4 ONE; 3 BROMO 2,3,7,8 TETRAHYDRO 4H,6H [1,4]OXAZEPINO[2,3,4 IJ]QUINOLIN 4 ONE; 3 BROMO 9 CHLORO 2,3,7,8 TETRAHYDRO 4H,6H [1,4]OXAZEPINO[2,3,4 IJ]QUINOLIN 4 ONE; 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 8 CHLORO 2 METHYL 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 8 CHLORO 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 8 HYDROXY 1,2,3,4 TETRAHYDROQUINOLINE; 8,10 DIBROMO 2 METHYL 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 8,10 DIBROMO 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 8,10 DICHLORO 2 METHYL 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 8,10 DICHLORO 6,7 DIHYDRO 5H [1,4]OXAZINO[2,3,4 IJ]QUINOLIN 3(2H) ONE; 9 CHLORO 2,3,7,8 TETRAHYDRO 4H,6H [1,4]OXAZEPINO[2,3,4 IJ]QUINOLIN 4 ONE; 9,11 DIBROMO 2,3,7,8 TETRAHYDRO 4H,6H [1,4]OXAZEPINO[2,3,4 IJ]QUINOLIN 4 ONE; 9,11 DICHLORO 2,3,7,8 TETRAHYDRO 4H,6H [1,4]OXAZEPINO[2,3,4 IJ]QUINOLIN 4 ONE; ACETIC ACID; CHEMICAL COMPOUND; ETHYL (8 QUINOLOXY)ACETATE; OMEGA (8 QUINOLYLOXY)ALKYL ESTER; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

AMIDATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION TIME;

EID: 79959380634     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260056     Document Type: Article

References (25)

1. Czarnik A W., Acc. Chem. Res. 1996 29 112
2. Fagnoni M, Heterocycles 2003 60 1921
3. Hazos G, Riedl Z, Kollenz G, Eur. J. Org. Chem. 2001 3405
4. Majumdar K C., Basu P K., Mukhopadhyay P P., Tetrahedron 2004 60 6239
5. Barchechath S D., Tawatao R I., Corr M, Carson D A., Cottam H B., Bioorg. Med. Chem. Lett. 2005 15 1785
6. Brana M F., Cacho M, Gradillas A, Pascual-Teresa B, Ramos A, Curr. Pharm. Des. 2001 7 1745
7. Martinez R, Chacon-Garcia L, Curr. Med. Chem. 2005 12 127
8. White J D., Yager K M., Yakura T, J. Am. Chem. Soc. 1994 116 1831
9. Tsushima K, Osumi T, Matsuo N, Itaya N, Agric. Biol. Chem. 1989 53 2529
10. Nishiyama T, Hashiguchi Y, Sakata T, Sakaguchi T, Polym. Degrad. Stab. 2003 79 225
11. Shikhaliev K S., Shmyreva Z, Gurova E M., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Technol. 1989 32 85; Chem. Abstr. 1990, 112, 216659a
12. Hashimoto K, Okaichi Y, Nomi D, Miyamoto H, Bando M, Kido M, Fujimura T, Furuta T, Minamikawa J.-I, Chem. Pharm. Bull. 1996 44 642
13. Shaaban M A., Ghoneim K M., Kalifa M, Pharmazie 1997 32 90
14. Collin J, Jaber N, Lannou M I., Tetrahedron Lett. 2001 42 7405
15. Dutta R, Mandal D, Panda N, Mondal N B., Banerjee S, Kumar S, Weber M, Luger P, Sahu N P., Tetrahedron Lett. 2004 45 9361
16. Paira P, Hazra A, Sahu K B., Banerjee S, Mondal N B., Sahu N P., Weber M, Luger P, Tetrahedron 2008 64 4026
17. Paira P, Paira R, Hazra A, Naskar S, Sahu K B., Saha P, Mondal S, Maity A, Banerjee S, Mondal N B., Tetrahedron Lett. 2009 50 4619
18. Paira P, Paira R, Hazra A, Sahu K B., Naskar S, Saha P, Mondal S, Maity A, Banerjee S, Mondal N B., Tetrahedron Lett. 2009 50 5505
19. Kaufman D, Johnson E, Mosher M D., Tetrahedron Lett. 2005 46 5613
20. DaCosta C S. J., Pais K C., Fernandes E L., deOliveira P S. M., Mendonça J S., DeSouza M V. N., Peralta M A., Vasconcelos T R. A., ARKIVOC 2006 (i) 128
21. Ranu B C., Jana U, Sarkar A, Synth. Commun. 1998 28 485
22. Tafel J, Ber. Dtsch. Chem. Ges. 1894 27 825
23. Kocian O, Ferles M, Collect. Czech. Chem. Commun. 1978 43 1413
24. Gauffre J C., Grignon-Dubois M, Rezzonico B, Léger M, J. Org. Chem. 2002 67 4696
25. Zhuravleva A Yu, Zimichev V A., Zemtsova N M., Klimochkin N Yu, Russ. J. Org. Chem. (Engl. Transl.) 2009 45 609