Cycloaddition in Synthesis of Sulfonamide Derivatives.I. A New Method for Preparation of N-(C-Aminoalkylthiomethylene) benzenesulfonamide

TSUNEO IWAKAWA; HIROTO TAMURA; TOMOHIRO SATO; YOSHIO HAYASE

doi:10.1248/cpb.36.4755

Cycloaddition in Synthesis of Sulfonamide Derivatives.I.

A New Method for Preparation of N-(C-Aminoalkylthiomethylene) benzenesulfonamide

TSUNEO IWAKAWA, HIROTO TAMURA, TOMOHIRO SATO, YOSHIO HAYASE

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Keywords: benzenesulfonyl isocyanate, [2+2] cycloaddition, dithiocarbamate, N-(Camino-alkylthiomethylene) benzenesulfonamide, X-ray structure analysis

JOURNAL FREE ACCESS

1988 Volume 36 Issue 12 Pages 4755-4759

DOI https://doi.org/10.1248/cpb.36.4755

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Abstract

A novel [2+2] cycloaddition reaction of benzenesulfonyl isocyanate is reported which canserve as a new, general method for the preparation of N-(C-amino-alkylthiomethylene) benzenesulfonamide. Benzenesulfonyl isocyanates underwent a [2+2] cycloaddition reaction with dithiocarbamates, which were obtained by treating amines with carbon disulfide and potassiumcarbonate, to give N-(C-amino-alkylthiomethylene) benzenesulfonamides in good yields.

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