Formation of unexpected product in the reaction of ۵-methoxycarbonylmethylydene-۱-۳-thiazolidine-۴-one with phenethylcarbamodithioic acid

We have successfully rapid synthesis of new derivative of ۵-methoxycarbonylmethylydene-۱,۳-thiazolidin-۴-one ۲ from the reaction between N,N’-disubstituted thiourea and dimethylacetylenedicarboxylate. In the following , we investigated the reaction between ۲ and phenethyl carbamodithioic acid ۳. Contrary to expectation, instead of product (۲E,۵E)-۳-isobutyl-۲-(isobutylimino)-۳'-phenethyl-۲'-thioxo-۲,۲',۳,۳'-tetrahydro-۴H,۴'H-[۵,۵'-bithiazolylidene]-۴,۴'-dione ۵, the product (E)-۵-(۱,۳-diisobutyl-۵-oxo-۲-thioxoimidazolidin-۴-ylidene)-۳-phenethyl-۲-thioxothiazolidin-۴-one ۴ was obtained. Through extensivespectroscopic analysis, including ۱H NMR, ۱۳C NMR, and HMBC, we identify the product and elucidate thestructure.

کلیدواژه ها:

N ، N’-disubstituted thiourea derivatives ، dithiocarbamates ، Rhodanine-۲-Thioxo-۴-imidazolidinone