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Reaction of Allenyl Esters with Sodium Azide: An Efficient Synthesis of E-Vinyl Azides and Polysubstituted Pyrroles

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Xian Huang,*^†^‡ Ruwei Shen,^† and Tiexin Zhang^†

Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou 310028, P. R. China, and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China huangx@mail.hz.zj.cn

J. Org. Chem., 2007, 72 (4), pp 1534–1537

DOI: 10.1021/jo062376m

Publication Date (Web): January 19, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

Zhejiang University.

‡

Shanghai Institute of Organic Chemistry.

Abstract

The nucleophilic addition of sodium azide to 1,2-allenyl esters can generate vinyl azides in excellent yields with excellent regio- and stereoselectivities. Moreover, pyrroles are synthesized using 1-allyllic 1,2-allenyl esters as substrates in t-BuOH at 65 °C. The sequential reaction for pyrroles is developed on the basis of a novel domino process involving nucleophilic addition, cycloaddition, denitrogenation, and aromatization.

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Published In Issue February 16, 2007
Received November 17, 2006

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Reaction of Allenyl Esters with Sodium Azide: An Efficient Synthesis of E-Vinyl Azides and Polysubstituted Pyrroles