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Synfacts 2006(8): 0770-0770  
DOI: 10.1055/s-2006-941976
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

A New Approach to Substituted Pyrrolotriazoles

Contributor(s): Victor Snieckus, Yigang Zhao
W. Chen, C. Su, X. Huang*
Zhejiang University, Hangzhou and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

An efficient synthesis of substituted pyrrolo[1,2,3]triazoles 3 is reported. 2,4-Diiodo­butenes 1, which are conveniently prepared by diiodination of methylenecyclopropanes (H. W. Zhou et al. Synlett 2003, 2080-2082), undergo the expected iodo to azide transformation, subsequent 1,3-dipolar cycloaddition in the same pot, followed by intramolecular Heck reaction furnishing pyrrolotriazoles 3. However, when 1,2,3-triazoles 2 containing a vinyl hydrogen were employed, only the elimination products 4 were obtained.