REACTIONS OF ORTHO-HALOACETOPHENONES WITH CARBON-DISULFIDE AND PHENYLISOTHIOCYANATE

被引:83
作者
RUDORF, WD
SCHIERHORN, A
AUGUSTIN, M
机构
[1] Sektion Chemie der Martin-Luther-Universität Halle-Wittenberg
关键词
D O I
10.1016/0040-4020(79)80155-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
O-Haloacetophenones 1 react with carbon disulfide in the presence of sodium hydride and an alkylating reagent to ketene S,S-acetals 3 and 4. The formation of 1-thiochromones 5 is possible, when the reaction is carried out at 100°. Treatment of 3a with aniline and guanidine, respectively, leads to the ketene N,N-acetal 6 and the 2-aminopyrimidine 7, respectively Reaction of 1 with phenyl isothiocyanate/sodium hydride and following alkylation gives ketene S,N-acetals 9, thiazolidones 14 and thiazolidine 15. Cyclisation of 9 in a basic medium forms the 4(1H)-quinolones 11. The physical properties of synthesized compounds are characterized by means of mass, 1H NMR, and IR spectra. The possible modes of formation are discussed. © 1979.
引用
收藏
页码:551 / 556
页数:6
相关论文
共 13 条