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A selective synthesis of β-isothiocyanato ketones through a Staudinger/aza-Wittig reaction of β-azido ketones

Research paper by Anastasia A. Fesenko, Ekaterina A. Dem’yachenko, Galina A. Fedorova, Anatoly D. Shutalev

Indexed on: 01 Dec '12Published on: 01 Dec '12Published in: Monatshefte für Chemie - Chemical Monthly



Abstract

A novel selective two-step synthesis of β-isothiocyanato ketones from α,β-unsaturated ketones has been developed. The synthesis includes preparation of β-azido ketones followed by reaction with triphenylphosphine and carbon disulfide. Treatment of the obtained β-isothiocyanato ketones with ammonia or methylamine gives corresponding hexahydro-4-hydroxypyrimidine-2-thiones. The latter are also prepared directly from β-azido ketones without isolation of the intermediate β-isothiocyanato ketones.

Graphical abstract 10.1007/s00706-012-0869-3.gif