Heterocyclization of thiocarbonohydrazides: Facile synthesis of 5-unsubstituted-1,3,4-thiadiazoles

2-(Hydrazinecarbothioyl)-N-substituted hydrazinecarbothioamides react with 2,3,5,6-tetrachloro-1,4-benzoquinone in high yields in a novel fast and facile method to give 5-unsubstituted-1,3,4-thiadiazole-2-amine derivatives. The synthesized compounds were characterized by spectroscopic methods and confirmed by using X-ray crystallography. A rationale for the formation of the products is presented.

Graphical abstractSynthesis of 5-unsubstituted-1,3,4-thiadiazole-2-amine derivatives via the reaction between 2-(hydrazinecarbothioyl)-N-susbstituted hydrazinecarbothioamides with 2,3,5,6-tetrachloro-1,4-benzoquinone.Figure optionsDownload full-size imageDownload as PowerPoint slide