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.

PDF syn_stu_46-22_3067_2014.pdf - Published Version Restricted to Registered users only Download (241kB) | Request a copy

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
Publication:	SYNTHESIS-STUTTGART
Publisher:	GEORG THIEME VERLAG KG
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
Date Deposited:	20 Dec 2014 04:36
Last Modified:	20 Dec 2014 04:36
URI:	http://eprints.iisc.ac.in/id/eprint/50478

Actions (login required)

View Item