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