4.4 Article

Three-component one-pot synthetic route to 2-amino-5-alkylidene-thiazol-4-ones

Journal

TETRAHEDRON
Volume 65, Issue 1, Pages 344-350

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.045

Keywords

2-Amino-5-alkylidene-thiazol-4-one; Rhodanine; Knoevenagel condensation; Multi-component reaction; Parallel synthesis; Microwave-assisted organic synthesis

Funding

  1. European Union [LSHM-CT 2004-512138]

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A fast and straightforward three-component reaction to 2-amino-5-alkylidene-thiazol-4-ones is described. The one-pot methodology, reported for the first time, involves Knoevenagel condensation of aromatic aldehydes and rhodanine followed by displacement of the thiocarbonyl sulfur with primary or secondary amines in the same reaction mixture. The reactions were performed using a dedicated microwave reactor, which enabled short reaction times and easy work-up. (C) 2008 Elsevier Ltd. All rights reserved.

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