2-Aminothiabutadiene as Useful Building Block in the Synthesis of 2-Aminothiopyrans and 2-Aminothiophenes

Aélig Robin; Jean-Claude Meslin; David Deniaud

doi:10.1055/s-2004-829112

PAPER

2-Aminothiabutadiene as Useful Building Block in the Synthesis of 2-Aminothiopyrans and 2-Aminothiophenes

Aélig Robin, Jean-Claude Meslin, David Deniaud*
Laboratoire de Synthèse Organique, UMR CNRS 6513, Faculté des Sciences et des Techniques, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
Fax: +33(2)51125402; e-Mail: david.deniaud@chimie.univ-nantes.fr;

Abstract

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Abstract

We report a reliable and regiocontrolled alternative route to unsubstituted 2-aminothiopyrans and 2-aminothiophenes. These sulfur heterocycles were prepared by reaction of protected aminothiabutadiene 1 with acrylic dienophiles or acceptor-substituted halomethyl compounds. All compounds were fully characterized by IR, HRMS, and ¹³C and ¹H NMR spectroscopy.

Key words

cycloaddition - thiophenes - thiopyrans - heterocycles - alkylations

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References

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