InCl3-Catalyzed Tandem Michael/Friedel-Crafts Cyclization: A Novel Protocol for Chiral 2,4-Disubstituted Tetrahydroquinolines

Synthesis

Volumn , Issue 3, 2004, Pages 405-408

  Yadav, J S ^a   Reddy, B V S ^a   Padmavani, B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Arylamines; Benzo fused heterobicycles; , unsaturated aldehydes

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

ARYLAMINES; CYCLIZATION;

CHEMICAL REACTIONS;

INDIUM CHLORIDE; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; MICHAEL ADDITION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 1442311006     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815942     Document Type: Article

References (17)

1. (a) Ramesh, M.; Mohan, P. A.; Shanmugam, P. Tetrahedron 1984, 40, 4041.
2. (b) Jurd, L.; Wong, R. V. Aust. J. Chem. 1981, 34, 1625.
3. (c) Coppola, G. M. J. Heterocycl. Chem. 1983, 20, 1217.
4. (a) Yamada, N.; Kadowaki, S.; Takahashi, K.; Umezu, K. Biochem. Pharmacol. 1992, 44, 1211.
5. (b) Faber, K.; Stueckler, H.; Kappe, T. J. Heterocyl. Chem. 1984, 21, 1177.
6. (c) Johnson, J. V.; Rauckman, B. S.; Baccanari, D. P.; Roth, B. J. Med. Chem. 1989, 32, 1942.
7. (a) Yadav, J. S.; Reddy, B. V. S.; Kumar, G. M. Synlett 2001, 1417.
8. (b) Yadav, J. S.; Sunny, A.; Reddy, B. V. S.; Sabitha, G. Synthesis 2001, 2165.
9. (c) Yadav, J. S.; Sunny, A.; Reddy, B. V. S.; Sabitha, G. Tetrahedron Lett. 2001, 42, 8063.
10. (d) Yadav, J. S.; Reddy, B. V. S.; Kumar, G. M. Synlett 2001, 1781.
11. (a) Li, C. J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
12. (b) Babu, G.; Perumal, P. T. Aldrichima Acta. 2000, 33, 16.
13. (c) Ghosh, R. Indian J. Chem., Sect. B 2001, 40, 550.
14. (a) Bandini, M.; Giorgio Cozzi, P.; Melchiorre, P.; Umani-Ronchi, A. Tetrahedron Lett. 2001, 42, 3041.
15. (b) Ceschi, M. A.; Felix, L. A.; Peppe, C. Tetrahedron Lett. 2000, 41, 9695.
16. Acyclic δ-hydroxy-α,β-unsaturated aldehyde was prepared from D-glucal using a known procedure reported in literature: Wengel J., Lau J., Pedersen E. B.; Synthesis; 1989, 829
17. The product 3a was also obtained from glucal triacetate and aniline, see: Yadav, J. S.; Reddy, B. V. S.; Rao, K. V.; Saritha Raj, K.; Prasad, A. R.; Kiran Kumar, S.; Kunwar, A. C.; Jayaprakash, P.; Jagannadh, B. Angew. Chem., Int. Ed. 2003, 42, 5198.