Intramolecular 6-endo-dig-Cyclization of Ethyl 5-Aminomethyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate

被引：1
|
作者：
Remizov, Yu. O. [1 ]
Pevzner, L. M. [1 ]
Petrov, M. L. [1 ]
机构：
[1] Tech Univ, St Petersburg State Inst Technol, Moskovskii Pr 26, St Petersburg 190013, Russia
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2019年 / 89卷 / 10期
关键词：
1,2,3-thiadiazoles; 4-(furan-3-yl)-1,2,3-thiadiazoles; furo[2,3-c]pyridines; 1,3-thiazolium salts; 1,3-thiazolo[3,2-a]pyridines;
D O I：
10.1134/S1070363219100268
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reaction of 5-aminomethyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid ethyl ester with bases has given ethyl 5-sulfanylidene-4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylate as a result of intramolecular 6-endo-dig-cyclization of thioketene generated in situ with an internal CH2NH2 nucleophile. The obtained ester has been alkylated with iodomethane at the sulfur atom to form ethyl 5-methylsulfanyl-4,7-dihydrofuro[2,3-c] pyridine-2-carboxylate. The Hantzsch reaction with omega-bromoacetophenone has resulted in the formation of 7-ethoxycarbonyl-3-phenylfuro[3,2-d][1,3]thiazolo[3,2-a]pyridin-4-ium bromide.
引用
收藏
页码：2151 / 2153
页数：3
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