Synthesis 2005(14): 2307-2314  
DOI: 10.1055/s-2005-870012
PAPER
© Georg Thieme Verlag Stuttgart · New York

2-Benzazepine Analogues from d-Glucose: Synthesis of Chiral cis- and trans-Fused Furo[3,2-c][2]benzazepine Derivatives

Tirtha Pada Majhi, Aniruddha Nandi, Arpita Neogi, Ranjan Mukhopadhyay, Partha Chattopadhyay*
Division of Medicinal Chemistry, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata 700 032, India
Fax: +91(33)24735197; e-Mail: partha@iicb.res.in;
Further Information

Publication History

Received 16 March 2005
Publication Date:
13 July 2005 (eFirst)

Abstract

Facile annulation of benzazepines onto furano-sugars has been achieved through Pd-catalyzed intramolecular cyclization. Using diisopropylidene d-glucose as a starting material, the first chiron approach to furobenzazepines in both cis and trans forms selectively introduced a 7-membered azepine ring linearly fused to a sugar nucleus. Cleavage of the sugar ring of the tricyclic derivatives provide a convenient route for entry into chiral functionalized 2-benzazepines, viz. 15 from 12a, and 16 from 14.

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15

1H NMR assignments are based on 1H-1H COSY results.

18

Restricted rotation of the amide CN bonds in the carbamate derivatives of benzazepines (12a-c, 14, 15 or 16) are likely to have caused multiplicity of 1H and 13C signals (in 1:1 or 1:2 ratio).