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Synthesis 2015; 47(02): 256-262
DOI: 10.1055/s-0034-1379253
DOI: 10.1055/s-0034-1379253
paper
Synthesis of Thioalkyne-Substituted Thiazolidine-2-thiones Using Tris(trimethylsilyl)methyllithium and Carbon Disulfide
Further Information
Publication History
Received: 22 July 2014
Accepted after revision: 18 September 2014
Publication Date:
06 November 2014 (online)
Abstract
An efficient, environmentally benign, and simple one-pot approach to the synthesis of 5-(iodomethyl)thiazolidine-2-thiones via multicomponent reaction of allylamines, carbon disulfide, and iodine under solvent-free conditions is presented. The obtained 5-(iodomethyl)thiazolidine-2-thiones were converted into silyl-protected terminal [(ethynylthio)methyl]-substituted thiazolidine-2-thiones by treatment with lithium 2,2,2-tris(trimethylsilyl)ethanedithioate, produced by the reaction of tris(trimethylsilyl)methyllithium with carbon disulfide.
Key words
thioalkyne - thiazolidine-2-thione - organosilicon - organosulfur - tris(trimethylsilyl)methyllithium - carbon disulfideSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/
10.1055/s-00000084.
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