REACTION OF 5-(2-FURYL)-1-METHYL-1H- AND 1-METHYL-5-(2-THIENYL)-1H-IMIDAZOLES WITH ELECTROPHILIC REAGENTS

被引：0

作者：

Vlasova, E. V. ^{[1
]}

Aleksandrov, A. A. ^{[1
]}

Elchaninov, M. M. ^{[1
]}

Milov, A. A. ^{[2
]}

Lukyanov, B. S. ^{[3
]}

机构：

[1] S Russian State Tech Univ, Novocherkassk 346428, Russia

[2] Russian Acad Sci, So Sci Ctr, Rostov Na Donu 344006, Russia

[3] So Fed Univ, Inst Phys & Organ Chem, Rostov Na Donu 344090, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2011年 / 47卷 / 06期

关键词：

1-methyl-5-(2-thienyl)-1H-imidazole; 5-(2-furyl)-1-methyl-1H-imidazole; quantum-chemical calculations; directing effect of substituents; electrophilic substitution;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-(2-Furyl)-1-methyl-1H-and 1-methyl-5-(2-thienyl)-1H-imidazoles were synthesized. The electron-withdrawing effect of the 5- and 2-imidazole substituents on the furan ring was studied by H-1 NMR spectroscopy and quantum-chemical calculations. Some electrophilic substitution reactions were investigated (nitration, bromination, sulfonation, hydroxymethylation, formylation, and acylation). In some cases, depending on the reaction conditions, both the furan and thiophene ring and the imidazole fragment undergo electrophilic attack.

引用

页码：684 / 689

页数：6

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