Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts

Tetrahedron

Volumn 63, Issue 9, 2007, Pages 1946-1952

  Kumar, Atul ^a   Maurya, Ram Awatar ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Green synthesis; Hantzsch reaction; Multicomponent reaction; Organocatalyst; Polyhydroquinoline derivatives

Indexed keywords

2,7,7 TRIMETHYL 5 OXO 4 (1 NAPHTHYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (3 METHOXYPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID TERT BUTYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (3 METHOXYPHENYL) 3 ACETYL 1,4,5,6,7,8 HEXAHYDROQUINOLINE; 2,7,7 TRIMETHYL 5 OXO 4 (3 NITROPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (3,4 DICHLOROPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (4 CHLOROPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (4 DIMETHYLAMINOPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (4 DIMETHYLAMINOPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID TERT BUTYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (4 METHOXYCINNAMYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (4 METHOXYCINNAMYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (4 METHYLPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 (4 METHYLPHENYL) 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID METHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 PHENYL 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 2,7,7 TRIMETHYL 5 OXO 4 PHENYL 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID TERT BUTYL ESTER; CINCHONIDINE; HYDROXYPROLINE; PHENYLGLYCINE; PROLINE; PROLINE DERIVATIVE; QUINOLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; ROOM TEMPERATURE;

EID: 33846336715     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.074     Document Type: Article

References (40)

1. Bossert F., Meyer H., and Wehinger E. Angew. Chem., Int. Ed. Engl. 20 (1981) 762-769
2. Nakayama H., and Kasoaka Y. Heterocycles 42 (1996) 901-909
3. Buhler F.R., and Kiowski W. J. Hypertens. 5 (1987) S3
4. Reid J.L., Meredith P.A., and Pasanisi F. J. Cardiovasc. Pharmacol. 7 (1985) S18
5. Godfaid T., Miller R., and Wibo M. Pharmacol. Rev. 38 (1986) 321-327
6. Sausins A., and Duburs G. Heterocycles 27 (1988) 279-289
7. Mager P.P., Coburn R.A., Solo A.J., Trigle D.J., and Rothe H. Drug Des. Discov. 8 (1992) 273-289
8. Mannhold R., Jablonka B., Voigdt W., Schoenafinger K., and Schravan K. Eur. J. Med. Chem. 27 (1992) 229-235
9. Klusa V. Drugs Future 20 (1995) 135-138
10. Bretzel R.G., Bollen C.C., Maester E., and Federlin K.F. Am. J. Kidney. Dis. 21 (1993) 54-63
11. Bretzel R.G., Bollen C.C., Maester E., and Federlin K.F. Drugs Future 17 (1992) 465-468
12. Boer R., and Gekeler V. Drugs Future 20 (1995) 499-509
13. Zhang D., Wu L.Z., Zhou L., Han X., Yang Q.Z., Zhang L.P., and Tung C.H. J. Am. Chem. Soc. 126 (2004) 3440-3441
14. Eynde J.J.V., Delfosse F., Mayence A., and Haverbeke Y.V. Tetrahedron 51 (1995) 6511-6516
15. Anniyappan M., Muralidharan D., and Perumal P.T. Tetrahedron 58 (2002) 5069-5073
16. Heravi M.M., Behbahani F.K., Oskooie H.A., and Shoar R.H. Tetrahedron Lett. 46 (2005) 2775-2777
17. Esfahani M.N., Moghadam M., Tangestaninejad S., Mirkhani V., and Momeni A.R. Bioorg. Med. Chem. 14 (2006) 2720-2724
18. Loev B., and Snader K.M. J. Org. Chem. 30 (1965) 1914-1916
19. Tu S.-J., Zhou J.-F., Deng X., Cai P.-J., Wang H., and Feng J.-C. Chin. J. Org. Chem. 21 (2001) 313-316
20. Sabita G., Reddy G.S.K.K., Reddy C.S., and Yadav J.S. Tetrahedron Lett. 44 (2003) 4129-4131
21. Ji S.J., Jiang Z.Q., Lu J., and Loh T.P. Synlett (2004) 831-835
22. Breitenbucher J.G., and Figliozzi G. Tetrahedron Lett. 41 (2000) 4311-4315
23. Dondoni A., Massi A., Minghini E., and Bertolasi V. Tetrahedron 60 (2004) 2311-2326
24. Wang L.M., Sheng J., Zhang L., Han J.W., Fan Z.Y., Tian H., and Qian C.T. Tetrahedron 61 (2005) 1539-1543
25. Ko S., and Yao C.-F. Tetrahedron 62 (2006) 7293-7299
26. Maheswara M., Siddaiah V., Damu G.L.V., and Rao C.V. ARKIVOC (2006) 201-206
27. Chandrasekhar S., Reddy N.S., Sultana S.S., Narsihmulu C., and Reddy K.V. Tetrahedron 62 (2006) 338-345
28. Li H., Wang B., and Deng L. J. Am. Chem. Soc. 128 (2006) 732-733
29. Poulsen T.B., Bernardy L., Bell M., and Jorgensen K.A. Angew. Chem., Int. Ed. 45 (2006) 1-5
30. Rasalkar M.S., Potdar M.K., Mohile S.S., and Salunkhe M.M. J. Mol. Catal. A: Chem. 235 (2005) 267-270
31. Alcaide B., Almendros P., Luna A., and Torres M.S. J. Org. Chem. 71 (2006) 4818-4822
32. Bogevig A., Kumaragurubaran N., Juhl K., Zhuang W., and Jorgensen K.A. Angew. Chem., Int. Ed. 41 (2002) 1790-1793
33. Janey J.M., Hsiano Y., and Armstrong III J.D. J. Org. Chem. 71 (2006) 390-392
34. Kumaragurubaran N., Juhl K., Zhuang W., Bogevig A., and Jorgensen K.A. J. Am. Chem. Soc. 124 (2002) 827-833
35. Kotrusz P., and Toma S. Molecules 11 (2006) 197-205
36. Ramachary D.B., Chowdari N.S., and Barbas III C.F. Angew. Chem. 115 (2003) 4365-4369
37. Kotrusz P., and Toma S. ARKIVOC (2006) 100-109
38. Hossein A.O., Elham R., and Majid M.H. J. Chem. Res. (2006) 246-247
39. Yadav J.S., Kumar S.P., Kondaji G., Rao R.S., and Nagaiah K. Chem. Lett. 33 (2004) 1168-1169
40. Mabry J., and Ganem B. Tetrahedron Lett. 47 (2006) 55-56