1,3,4-Thiadiazoles and 1,3-thiazoles from one-pot reaction of bisthioureas with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate

ABSTRACT

Bisthioureas reacted with either 2-(bis(methylthio)methylene)malononitrile or ethyl 2-cyano-3,3-bis(methylthio)acrylate to give 1,3,4-thiadiazoles and 1,3-thiazoles. Only, the reactive allyl derivative of bisthioureas reacted with the bis(methylthio)methylene compounds to give 1,3-thiazoles. The mechanism was discussed. The structures of products were proved by MS, IR, NMR and elemental analyses and X-ray structure analysis.

GRAPHICAL ABSTRACT

KEYWORDS:

• Bisthioureas
• bis(methylthio)malononitrile
• bis(methylthio)acrylate
• 1,3,4-thiadiazoles
• 1,3-thiazoles
• X-ray

Disclosure statement

No potential conflict of interest was reported by the authors.

Acknowledgements

We thank the DFG (BR 1750) for its financial support for the stay of Professor Aly at the Karlsruhe Institute of Technology, Institute of Organic Chemistry, Germany