Synthesis and Some Properties of 2-(Furan-2-yl)[1,3]thiazolo[4,5-b]pyridine

被引：1
|
作者：
Aleksandrov, A. A. [1 ]
Elchaninov, M. M. [1 ]
Tarakanova, Yu E. [1 ]
Tishina, D. A. [1 ]
Shmanovsky, M. L. [1 ]
Baidin, A. A. [1 ]
机构：
[1] Platov South Russian State Polytech Univ, Novocherkassk 346428, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 57卷 / 12期
关键词：
2-aminopyridine; N-(pyridin-2-yl)furan-2-carboxamide; carbothioamide; oxidation; potassium ferricyanide; electrophilic substitution;
D O I：
10.1134/S1070428021120137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The acylation of pyridin-2-amine with furan-2-carbonyl chloride in propan-2-ol gave N-(pyridin-2-yl)furan-2-carboxamide, and treatment of the latter with excess P2S5 in anhydrous toluene afforded the corre-sponding carbothioamide which was oxidized with potassium ferricyanide in alkaline medium to 2-(furan-2-yl)-[1,3]thiazolo[4,5-b]pyridine. The product was subjected to electrophilic substitution reactions such as nitration, bromination, hydroxymethylation, formylation, and acylation, where the substituent entered exclusively the 5-position of the furan ring. The alkylation of the title compound with methyl iodide led to the formation of quaternization product at the pyridine nitrogen atom, whereas no amination according to Chichibabin was observed.
引用
收藏
页码：1983 / 1987
页数：5
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