A VERSATILE AND CONVENIENT METHOD FOR THE SYNTHESES OF PYRIMIDO[4,5-B][1,4]THIAZINE AND PYRIMIDO[4,5-B][1,4]THIAZEPINE RING-SYSTEMS

被引：3
|
作者：
SAKO, M
TOTANI, R
KONOHARA, M
HIROTA, K
MAKI, Y
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 11期
关键词：
D O I：
10.1039/p19910002675
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of 5-hydroxyuracil 1 and 5-hydroxyisocytosine 2 with N-bromosuccinimide in ethanol followed by the thermal condensation with beta- and gamma-amino thiols such as 2-aminothiophenol, cysteamine, L-cysteine and D,L-homocysteine resulted in the formation of the corresponding pyrimido[4,5-b][1,4]thiazin-4(3H)-ones, 3-8, and pyrimido[4,5-b][1,4]thiazepin-4(3H)-ones, 9 and 10. The new method for the construction of pyrimido[4,5-b][1,4]thiazine and -thiazepine ring systems was shown to involve the condensation of 5,6-diethoxy-5-hydroxy-5,6-dihydropyrimidin-4(3H)-one intermediates, 11 and 12, with the beta- and gamma-amino thiols which is accelerated in the presence of an acid-catalyst.
引用
收藏
页码：2675 / 2677
页数：3
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