SYNTHESIS AND APPLICATION OF IMIDAZOLE DERIVATIVES - SYNTHESIS OF 5-METHYL-7,8,9,10-TETRAHYDRO-5H-AZEPINO[1,2-A]BENZIMIDAZOL-7-ONE AND RELATED-COMPOUNDS

被引：6

作者：

OHTA, S

NARITA, Y

OKAMOTO, M

HATAKEYAMA, S

KAN, K

YUASA, T

HAYAKAWA, K

机构：

[1] Kyoto Pharmaceutical University, Kyoto 607, Misasagi-nakauchicho 5, Yamashina-ku

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 02期

关键词：

1-acylimidazole; 2-(2-furylidenemethyl)benzimidazole; azepino[1,2-α]benzimidazole; benzimidazole; rearrangement cyclization; stereochemistry; X-ray crystallography;

D O I：

10.1248/cpb.38.301

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

5-Methyl-7,8>9,10-tetrahydro-5H-azepino[l,2-a]benzimidazol-7-one (6) was synthesized by treating l-(3-car-boxypropyl)-2,3-dimethylbenzimidazolium iodide (11) with IJ’-carbonyldiimidazole in the presence of triethylamine. Refluxing 2-(5-chloro-2-oxopentyl)-l-methylbenzimidazole (4) in ethyl acetate did not afford 6 but gave (Z)-l-methyl-2-(2,3,4,5-tetrahydro-2-furylidenemethyl)benzimidazole (5), which was rearranged to the corresponding (E)-isomer (7) by heating in ethyl acetate in the presence of basic alumina. The structures of 5, 6 and 7 were determined by X-ray crystallography. © 1990, The Pharmaceutical Society of Japan. All rights reserved.

引用

页码：301 / 306

页数：6

共 17 条

[1] ADDITION REACTIONS OF HETEROCYCLIC COMPOUNDS .26. DIMETHYL ACETYLENEDICARBOXYLATE WITH IMIDAZOLES AND BENZIMIDAZOLES [J].