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

页码：953 / 963

页数：11

共 27 条

[1]

[Anonymous], 1975, CHEM HETEROCYC COMPO, DOI DOI 10.1007/BF00764522

[2]

[Anonymous], CHEM SOC PERKIN T

[3]

[Anonymous], 1994, ZH ORG KHIM

[4] PMR STUDY OF ETHYL ARYLHYDRAZONOCYANOACETYLCARBAMATES AND OF ARYLHYDRAZONO-2-CYANOMETHYLBENZIMIDAZOLE [J].

BEKAREK, V ;

SLOUKA, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1970, 35 (10) :2936-&

[5] RECYCLIZATION ON ACYLATION OF 1-METHYL-2-PHENACYL-1H-BENZIMIDAZOLE PHENYLHYDRAZONE [J].

Dzvinchuk, I. B. ;

Gutov, O. V. ;

Chernega, A. N. ;

Lozinskii, M. O. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (06) :684-690

[6]

Dzvinchuk I. B., 2007, SELECTED METHODS SYN, V6

[7]

Dzvinchuk I. B., 2006, NITROGEN CONTAINING, V1, P281

[8]

Dzvinchuk I. B., 2006, NITROGE CONTAININGN, V1, P275

[9]

Elguero J., 1976, TAUTOMERISM HETEROCY, p[190, 492]

[10]

FORESMAN JB, 2001, EXPLORING CHEM ELECT

← 1 2 3 →