One-Pot Synthesis of 5-Alkylthio-3H-1,2-dithiole-3-thiones: Advantages and Scopes

Mario L. Aimar; Rita H. de Rossi

doi:10.1055/s-2000-8202

Synthesis 2000; 2000(12): 1749-1755
DOI: 10.1055/s-2000-8202

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One-Pot Synthesis of 5-Alkylthio-3H-1,2-dithiole-3-thiones: Advantages and Scopes

Mario L. Aimar^* , Rita H. de Rossi

^*Instituto des Investigaciones en Fisico-Química de Córdoba (INFIQC), Departamento de Química Orgánica, Facultad de Ciencias Químicas, U.N.C. Ciudad Universitaria, (5000) Córdoba, Argentina; Fax + 54 (3 51) 4 33 30 30; E-mail: ritah@dqo.fcq.unc.edu.ar

Abstract

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The reaction of dialkyl malonate esters with P₂S₅/S₈ in boiling xylene in the presence of 2-mercaptobenzothiazole/ZnO as catalyst produces 5-alkylthio-3H-1,2-dithiole-3-thiones as major identifiable product. Moderate yields were obtained with malonate esters of primary alcohols. The reaction fails with malonate esters of secondary alcohols. Regarding the substituent in position two, dialkyl malonates with groups such as CH₃, Ph, CH₂Ph, OCH₃ and Cl afford the corresponding 4-substituted derivatives whereas with Br and NO₂ do not give the expected products. Some mechanistic evidences are described.

1,2-dithiole-3-thiones - sulfurization - malonate esters - cyclization - thiols - sulfur - heterocycles

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