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

来源：

TETRAHEDRON | 1979年 / 35卷 / 04期

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

页码：551 / 556

页数：6