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

Xian Huang,* Ruwei Shen and Tiexin Zhang

*Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou 310028, P. R. China, Email:

X. Huang, R. Shen, T. Zhang, J. Org. Chem., 2007, 72, 1534-1537.

DOI: 10.1021/jo062376m


The nucleophilic addition of sodium azide to 1,2-allenyl esters regio- and stereoselectively generates vinyl azides in excellent yields. A sequential reaction for the synthesis of pyrroles using 1-allyllic 1,2-allenyl esters as substrates is developed on the basis of a domino process involving nucleophilic addition, 1,3-dipolar cycloaddition, denitrogenation, and aromatization.

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Key Words

Vinyl Azides, Pyrroles

ID: J42-Y2007-0660