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Synthesis 2001(13): 1979-1984
DOI: 10.1055/s-2001-17709
PAPER
© Georg Thieme Verlag Stuttgart · New York

Bismuth(III) Chloride-Catalyzed Intramolecular Hetero Diels-Alder Reaction: Application to the Synthesis of Tetrahydrochromano[4,3-b]quinoline Derivatives [1]

Gowravaram Sabitha*, Erigala Venkata Reddy, Jhillu S. Yadav
Organic Division I, Indian Institute of Chemical Technology, Hyderabad, 500007, India
Fax: +91(40)7173757; e-Mail: sabitha@iict.ap.nic.in;
Further Information

Publication History

Received 18 April 2001
Publication Date:
10 August 2004 (online)

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Abstract

Intramolecular [4+2] cycloaddition reaction of aldimines derived from aromatic amines and O-allyl derivatives of salicylic aldehydes was efficiently catalyzed by BiCl3 to afford the corresponding tetrahydrochromano[4,3-b]quinolines in excellent yields. The products are isolated as 1:1 mixture of diastereoisomers.

Key words

Hetero Diels-Alder-reaction - bismuth(III) chloride - catalysis - tetrahydrochromanoquinolines

1

IICT communication No. 4779.

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IICT communication No. 4779.