Studies on Fungicides. XXII. Reaction of Dimethyl Acetylenedicarboxylate with Dithiocarbamates, Thiolcarbamates, Thiosemicarbazides and Thiosemicarbazones

Abstract

Dimethyl acetylenedicarboxylate was found to react readily with dithiocarbamates, thiolcarbamates, thiosemicarbazides and thiosemicarbazones to give 4-thiazolidones (I, IV, V, VI and VII). The exodouble bond of 4-thiazolidones (I) was highly reactive to dithiocarbamates to give 2, 2'-dithioxo-5, 5'-bi-4-thiazolidones (II), which were autoxydized to 2, 2'-dithioxo-Δ5, 5'-bi-4-thiazolidones (III) in the presence of catalytic amount of amines.