RING CONTRACTION OF 5-OXO-4-PHENYL-5,6-DIHYDRO-4H-1,3,4-THIADIAZINE WITH SODIUM METHOXIDE

被引：0
|
作者：
MATSUBARA, Y
KITANO, K
YAMADA, S
YOSHIHARA, M
MAESHIMA, T
机构：
来源：
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN | 1991年 / 111卷 / 11期
关键词：
5-OXO-4-PHENYL-5,6-DIHYDRO-4H-1,3,4-THIADIAZINE; 2-ANILINO-4-OXO-1,3-THIAZOLINE; 5-OXO-2,4-DIPHENYL-5,6-DIHYDRO-4H-1,3,4-THIADIAZINE; 5-OXO-2,4-DIPHENYL-4,5-DIHYDRO-4H-1,3,4-THIADIAZOLE; NITROGEN-NITROGEN BOND CLEAVAGE; RING CONTRACTION; REARRANGEMENT;
D O I：
10.1248/yakushi1947.111.11_672
中图分类号：
R9 [药学];
学科分类号：
1007 ;
摘要：
The reaction of 5-oxo-4-phenyl-5,6-dihydro-4H-1,3,4-thiadiazine (1a) with sodium methoxide in methanol at 35-degrees-C was found to give 2-anilino-4-oxo-1,3-thiazoline (2a) in a quantitative yield via cleavage of the nitrogen-nitrogen bond. The mechanisms of formation of 2 were discussed by a few kinetic studies using 4-p-substituted phenyl-5-oxo-5,6-dihydro-4H-1,3,4-thiadiazine (1b, c), and related reaction of 5-oxo-4-phenyl-4,5-dihydro-4H-1,3,4-thiadiazole (3), 5-oxo-2,4-diphenyl-5,6-dihydro-4H-1,3,4-thiadiazine (4) and 5-oxo-2,4-diphenyl-4,5-dihydro-4H-1,3,4-thiadiazole (5).
引用
收藏
页码：672 / 675
页数：4
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