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

AA Fesenko, EA Dem'yachenko, GA Fedorova…

Index: Fesenko, Anastasia A.; Dem'Yachenko, Ekaterina A.; Fedorova, Galina A.; Shutalev, Anatoly D. Monatshefte fur Chemie, 2013 , vol. 144, # 3 p. 351 - 359

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Citation Number: 4

Abstract

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- ...