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Synthesis of novel beta-aryl-beta-(methylthio)acroleins via Vilsmeier-Haack protocol as potential 1,3-dielectrophilic three-carbon building blocks

Gowda, Byre G and Charanraj, TP and Kumara, Pradeepa CS and Ramesh, N and Thomas, SP and Sadashiva, MP and Junjappa, H (2014) Synthesis of novel beta-aryl-beta-(methylthio)acroleins via Vilsmeier-Haack protocol as potential 1,3-dielectrophilic three-carbon building blocks. In: TETRAHEDRON LETTERS, 55 (32). pp. 4475-4479.

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Official URL: http://dx.doi.org/ 10.1016/j.tetlet.2014.06.065

Abstract

A new general route for the synthesis of novel beta-aryl-beta-(methylthio)acroleins, a class of stable potential 1,3-dielectrophilic synthons, has been reported. The overall protocol involves treatment of either beta-chloroacroleins or their precursor iminium salts (generated in situ from the corresponding active methylene ketones under Vilsmeier-Haack reaction conditions) with S,S-dimethyldithiocarbonates (DDC)/aqueous KOH in either a one-pot or two-step process. The dimethyldithiocarbonate (DDC)/30% aqueous KOH has been shown to be an excellent source of methylthiolate anion. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Id for Latest eprints
Date Deposited: 18 Sep 2014 09:10
Last Modified: 18 Sep 2014 09:10
URI: http://eprints.iisc.ac.in/id/eprint/49897

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