A General, Regioselective Synthesis of 2-Alkenylanilines

Michael Harmata; Mehmet Kahraman

doi:10.1055/s-1995-3986

Synthesis 1995; 1995(6): 713-716
DOI: 10.1055/s-1995-3986

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A General, Regioselective Synthesis of 2-Alkenylanilines

Michael Harmata^* , Mehmet Kahraman

^*Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA, Fax +1(314)8822754

Abstract

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Reduction of selected 2,1-benzothiazines with sodium amalgam leads to the formation of 2-alkenylanilines in high yield. The benzothiazines are readily available from the reaction of N-phenyl-S-(p-tolyl)sulfonimidoyl chloride with alkynes in the presence of aluminum chloride. The sulfonimidoyl chloride is derived from aniline, and the process described herein thus constitutes a high-yielding, regioselective functionalization of aniline.

vinylanilines - alkenylanilines - sulfoximines - benzothiazines - reduction

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