Studies on Fungicides. XXIV. Reaction of 5-Methoxycarbonylmethylidene-2-thioxo (or oxo)-4-thiazolidones with o-Aminobenzenethiol and Other Thiols

1 January 1974

journal article
Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 22 (1) , 42-49
https://doi.org/10.1248/cpb.22.42

Abstract

By a novel addition reaction of o-aminobenzenethiol to 5-methoxycarbonylmethylidene-2-thioxo (or oxo)-4-thiazolidones (I) were obtained 5-(3-oxo-2, 3-dihydro-4H-1, 4-benzothiazin-2-yl)-2-thioxo (or oxo)-4-thiazolidones (III). I was also found to reat with thiols to afford 1 : 1 adducts (II and VI) in the presence of a catalytic amount of triethylamine. Thermal cyclization of the adducts (II) to III was observed. The adducts (VI) were proved to dissociate into I and thiols when heated above their melting points or dissolved in acetone or ethanol. Oxidation of III and VI gave the dehydro-compounds (IV and VIII), respectively.

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