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

Cheerladinne Venkateswarlu; Srinivasan Chandrasekaran

doi:10.1055/s-0034-1378553

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(22): 3067-3074
DOI: 10.1055/s-0034-1378553

paper

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

Cheerladinne Venkateswarlu

Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, Karnataka, India Fax: +91(80)2360 2423 eMail: scn@orgchem.iisc.ernet.in

,

Srinivasan Chandrasekaran*

Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, Karnataka, India Fax: +91(80)2360 2423 eMail: scn@orgchem.iisc.ernet.in

› Institutsangaben

Abstract

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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 °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.

Key words

thio esters - ring opening - anhydrides - disulfides - reductions

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