SYNTHESIS OF 2-CHLORO-L-(BETA-D-RIBOFURANOSYL) BENZIMIDAZOLE AND CERTAIN RELATED DERIVATIVES

被引：37

作者：

REVANKAR, GR

TOWNSEND, LB

机构：

[1] Department of Chemistry, Department of Biopharmaceutical Sciences, University of Utah

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1968年 / 5卷 / 04期

关键词：

D O I：

10.1002/jhet.5570050407

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 2‐chloro‐1‐(β‐D‐ribofuranosyl)benzimidazole (4b) has been accomplished by a condensation of 2‐chloro‐1‐trimethylsilylbenzimidazole (1) with 2,3,5‐tri‐O‐acetyl‐D‐ribofuranosyl bromide (2) followed by subsequent deacetylation. Nucleophilic displacement of the 2‐chloro group has furnished several interesting 2‐substituted‐1‐(β‐D‐ribofuranosyl)benzimidazoles. 1‐(β‐D‐Ribofuranosyl)benzimidazole (5) and 1‐(β‐D‐ribofuranosyl)benzimidazole‐2‐thione (6) were prepared from 4b and 6 was also prepared by condensation of 2 with silylated benzimidazole‐ 2‐thione (3). Alkylation of 6 furnished certain 2‐alkylthio‐1‐(β‐D‐ribofuranosyl)benzimidazoles and oxidation of 6 with alkaline hydrogen peroxide produced 1‐(β‐D‐ribofuranosyl)benzimidazole‐2‐one (9). The assignment of anomeric configuration for all nucleosides reported is discussed. Copyright © 1968 Journal of Heterocyclic Chemistry

引用

页码：477 / &

共 25 条

[1]

Beaman A.G., 1965, ANTIMICROB AGENTS CH, P469

[2] VITAMIN-B12 .9. 1-ALPHA-D-RIBOFURANOSIDO-5,6-DIMETHYLBENZIMIDAZOLE, A DEGRADATION PRODUCT OF VITAMIN-B12 [J].