Studies on Fungicides. XXV. Addition Reaction of Dithiocarbamates to Fumaronitrile, Bis (alkylthio) maleonitrile, 2,3-Dicyano-5,6-dihydro-1,4-dithiin and 4,5-Dicyano-2-oxo-1,4-dithiole

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5-Cyanomethyl-2-thioxo-4-aminothiazolines (II) were prepared by the addition reaction of dithiocarbamates to fumaronitrile. In the reactions of bis (methylthio) maleonitrile (IXa), bis (benzylthio) maleonitrile (IXb), 2,3-dicyano-5,6-dihydro-1,4-dithiin (IXc) and 4,5-dicyano-2-oxo-1,4-dithiole (IXd) with dithiocarbamates were obtained 5,5'-bi-2-thioxo-4-aminothiazolines (X). The 4-amino groups of II and X were found to be labile and were hydrolyzed when heated with mineral acids to give 5-cyanomethyl-2-thioxo-4-thiazolidones (III) and 5,5'-bi-2-thioxo-4-thiazolidones (XII), respectively. X was also found to be converted to Δ^<5,5'>-bi-2-thioxo-4-iminothiazolidine (XI) by autoxidation in the presence of catalytic amount of triethylamine. 4-Oxo-4'-imino-Δ^<5,5'>-bi-2-thioxo-thiazolidine (XVI) was prepared by the addition reaction of N-benzyldithiocarbamate to 5-cyanomethylidene-2-thioxo-4-thiazolidone (XIV). XI and XIV gave Δ^<5,5'>-bi-2-thioxo-4-thiazolidones (XIII) on hydrolysis with mineral acids.
公益社団法人日本薬学会の論文
1974-03-25