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Tetrathiomolybdate-Mediated Ring Opening of Isatoic Anhydrides: An Entry to S-Alkyl or S-Aryl 2-Aminobenzenecarbothioate Derivatives

Venkateswarlu, Cheerladinne and Chandrasekaran, Srinivasan (2014) Tetrathiomolybdate-Mediated Ring Opening of Isatoic Anhydrides: An Entry to S-Alkyl or S-Aryl 2-Aminobenzenecarbothioate Derivatives. In: SYNTHESIS-STUTTGART, 46 (22). pp. 3067-3074.

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Official URL: http://dx.doi.org/ 10.1055/s-0034-1378553

Abstract

Decarboxylative thioesterification of isatoic anhydrides mediated by benzyl(triethyl)ammonium tetrathiomolybdate gave the corresponding S-alkyl or S-aryl 2-aminobenzenecarbothioate derivatives at 60 degrees C. At ambient temperature, organic disulfides were reductive cleaved in the presence of tetrathiomolybdate to generate thiolate anions in situ; this was followed by attack on isatoic anhydrides to give the corresponding S-alkyl or S-aryl 2-aminobenzenecarbothioate derivatives. Additionally, it was shown that multistep reactions could be performed with tetrathiomolybdate, starting with an alkyl halide as a precursor of an alkyl disulfide, which, in turn, was used for ring opening of isatoic anhydrides.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to the GEORG THIEME VERLAG KG, RUDIGERSTR 14, D-70469 STUTTGART, GERMANY
Keywords: thio esters; ring opening; anhydrides; disulfides; reductions
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 20 Dec 2014 04:36
Last Modified: 20 Dec 2014 04:36
URI: http://eprints.iisc.ac.in/id/eprint/50478

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