SYNTHESIS AND TAUTOMERISM OF 2-PHENACYL-1H-BENZIMIDAZOLES AND THEIR HYDROGEN BROMIDE SALTS

被引：5
|
作者：
Dzvinchuk, I. B. [1 ]
Nesterenko, A. M. [1 ]
Polovinko, V. V. [2 ]
Ryabitskii, A. B. [1 ]
Lozinskii, M. O. [1 ]
机构：
[1] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine
[2] Ukrorgsintez, UA-02042 Kiev, Ukraine
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2011年 / 47卷 / 08期
关键词：
benzimidazoles; acylation; deacylation; quantum-chemical study; spectroscopy; tautomerism;
D O I：
10.1007/s10593-011-0860-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Phenacyl-1H-benzimidazoles were prepared by the acylation of 2-methylbenzimidazole using aroyl chlorides with subsequent alcoholysis or aminolysis of the N,C,O-triacylation products obtained. Treatment of the 2-phenacyl-1H-benzimidazoles with hydrobromic acid gave the corresponding salts. The structure of the products was supported by IR, (1)H and (13)C NMR, and HMBC spectroscopy as well as by quantum-chemical calculations. 2-Phenacyl-1H-benzimidazoles in DMSO-d(6) solution were found to display predominantly imino-enamino tautomerism, while their salts were found to display predominantly keto-enol tautomerism.
引用
收藏
页码：953 / 963
页数：11
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