Bismuth triflate catalyzed condensation of δ-hydroxy-α,β- unsaturated aldehydes with aryl amines

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1543-1546

  Yadav, J S ^a   Reddy, B V S ^a   Parimala, G ^a   Krishnam Raju, A ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Arylamines; Bismuth reagents; Heterobicycles; Unsaturated aldehydes

Indexed keywords

ALDEHYDE DERIVATIVE; AROMATIC AMINE; BISMUTH DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 1642497622     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.043     Document Type: Article

References (16)

1. Boger D.L., Weinreb S.M. Hetero-Diels-Alder Methodology in Organic Synthesis. 1987;Academic, San Diego. Chapters 2 and 9.
2. Buonora P., Olsen J.C., Oh T. Tetrahedron. 57:2001;6099-6138.
3. Ramesh M., Mohan P.A., Shanmugam P. Tetrahedron. 40:1984;4041-4049.
4. Jurd L., Wong R.V. Aust. J. Chem. 34:1981;1625-1632.
5. Coppola G.M. J. Heterocycl. Chem. 20:1983;1217-1221.
6. Yamada N., Kadowaki S., Takahashi K., Umezu K. Biochem. Pharmacol. 44:1992;1211.
7. Faber K., Stueckler H., Kappe T. J. Heterocyl. Chem. 21:1984;1177-1178.
8. Johnson J.V., Rauckman B.S., Baccanari D.P., Roth B. J. Med. Chem. 32:1989;1942-1949.
9. Kobayashi S. Synlett. 1994;689-701.
10. Kobayashi S. J. Synth. Org. Chem. Jpn. 53:1995;370.
11. Kobayashi S. Eur. J. Org. Chem. 1999;15-27.
12. Leonard N.M., Wieland L.C., Mohan R.S. Tetrahedron. 58:2002;8373-8397.
13. Repichet S., Zwick A., Vendier L., Le Roux C., Dubac J. Tetrahedron Lett. 43:2002;993-995.
14. The acyclic α,β-unsaturated aldehydes were prepared from D-glucal using a procedure reported in the literature: Wengel J., Lau J., Pedersen E.B. Synthesis. 1989;829-831.
15. The product 3a was also obtained from glucal triacetate and aniline: see Ref. 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. 42:2003;5198-5201.
16. 5: 383.0368. Found: 383.0373.