CONVERSION OF 1,3-THIAZOLIDINE AND ITS SULFOXIDE TO DIHYDRO-1,4-THIAZINE

被引：9

作者：

LEE, WS ^{[1
]}

NAM, KD ^{[1
]}

HAHN, HG ^{[1
]}

MAH, HD ^{[1
]}

机构：

[1] KYONGGI UNIV,DEPT CHEM,SUWON 440270,SOUTH KOREA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1993年 / 30卷 / 04期

关键词：

D O I：

10.1002/jhet.5570300447

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two methods for constructing dihydro-1,4-thiazine 4 were described. 1,3-Thiazolidines 5 were converted to dihydro-1,4-thiazines 4 by chlorinolysis through the unisolable chlorosulfonium salt 10 and sulfenyl chloride 11. Oxidation of the sulfides 5 gave a mixture of pairs of diasteromers 6. In the presence of acid catalyst, both sulfoxides were converted to dihydrothiazine 4 through sulfenic acid 22. In this reaction the stepwise ring opening involving carbocation 23 seems more probable. The structures of 4 were proven by the independent synthesis involving 3-bromo-2-oxobutanoic acid derivatives.

引用

页码：1105 / 1109

页数：5

共 18 条

[1] POSITION OF PROTONATION AND MECHANISM OF HYDROLYSIS OF SIMPLE AMIDES [J].