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Synthesis 2003(8): 1231-1235
DOI: 10.1055/s-2003-39392
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Annulated 1,2,4-Triazoles. A Convenient Synthesis of Thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines: A Novel Triheterocyclic Ring System

Quanrui Wang*, Zheng Li, Haiyan Yang, Feng Li, Zongbiao Ding, Fenggang Tao
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. China
Fax: +86(21)65641740; e-Mail: qrwangb@online.sh.cn;
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Publication History

Received 7 January 2003
Publication Date:
26 May 2003 (online)

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Abstract

A synthetic approach to the previously unknown thieno[2,3-f][1,2,4]triazolo[1,5-a]azepine derivatives was efficiently accomplished by cycloaddition of the bicyclic 1-aza-2-azoniaallene salts 6, derived from 6,7-dihydrobenzo[b]thiophen-4(5H)-one hydrazones 4, to the triple bond of nitriles, followed by ring enlargement. The X-ray crystal diffraction analysis of the picrate 10a provided affirmative proof for the structural assignment made.

Key words

1-aza-2-azoniaallene cations - cycloaddition - nitriles - ring enlargement - thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines

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