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Synthesis 2007(11): 1629-1634  
DOI: 10.1055/s-2007-966059
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Approach to 4,5-Dihydro[1,2,4]triazolo[3,2-d][1,5]benzoxazepines

Qingqing Meng, Hexiang Bai, Zhiming Li, Quanrui Wang*, Fenggang Tao
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China
Fax: +86(21)65641740; e-Mail: qrwang@fudan.edu.cn;
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Publication History

Received 13 February 2007
Publication Date:
11 May 2007 (online)

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Abstract

The novel tricyclic heterocycles of 4,5-dihydro[1,2,4]triazolo[3,2-d][1,5]benzoxazepine derivatives were prepared by the cycloaddition of the corresponding bicyclic cationic 1,3-dipoles, which were easily generated from the azoacetates by reaction with AlCl3 as a Lewis acid, to the triple bond of nitriles along with the consecutive ring expansion. The formation of products deviating from the normal reaction aptitudes was observed and the mechanistic aspects are discussed herein. Crystal diffraction analysis for two of the products unequivocally established the respective structures proposed.

Key words

1-aza-2-azoniaallene cations - cycloaddition - nitriles - ring enlargement - benzoxazepine

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