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New Synthesis of peri -Fused Tetrahydro[1,3]diazepino[1,2- a ]benzimidazoles from 1-Aroylmethyl-2-[(4-hydroxybutyl)amino]benzimidazoles
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-11-24 , DOI: 10.1134/s1070428020100097
T. A. Kuzʼmenko , L. N. Divaeva , A. S. Morkovnik

Abstract

Treatment of 2-[(4-hydroxybutyl)amino]-1H-benzimidazole with ω-bromoacetophenones gave 1-aroylmethyl-substituted derivatives which underwent cyclization to 2-aryl-1-(4-bromobutyl)imidazo[1,2-a]benzimidazole hydrobromides on heating in concentrated hydrobromic acid when Ar = Ph, 4-ClC6H4, 4-BrC6H4, and 4-O2NC6H4. The corresponding bases were readily converted into peri-fused tetrahydro[1,3]diazepino[1,2-a]benzimidazoles via intramolecular alkylation with closure of seven-membered ring. If an electron-donating methoxy group was present in the aryl fragment of the initial ketone, 1-(4-hydroxyphenyl)-2-[2-(pyrrolidin-1-yl)-1H-benzimidazol-1-yl]ethan-1-one was formed in the reaction with HBr.



中文翻译:

1-芳酰基甲基-2-[[(4-羟基丁基)氨基]苯并咪唑类新合成全熔合四氢[1,3]二氮杂并[1,2-a]苯并咪唑

摘要

用ω-溴苯乙酮处理2-[((4-羟基丁基)氨基] -1 H-苯并咪唑得到1-芳酰基甲基取代的衍生物,将其环化为2-芳基-1-(4-溴丁基)咪唑并[1,2- a ]苯并咪唑氢溴酸盐在浓氢溴酸加热当Ar =苯基,4-CLC 6 ħ 4,4- BRC 6 ħ 4,和4-O 2 NC 6 H ^ 4。对应的碱基容易地转化为-融合四氢[1,3]二氮杂卓并[1,2苯并咪唑通过分子内烷基化与七元环的闭合而形成。如果初始酮的芳基片段中存在供电子甲氧基,则1-(4-羟苯基)-2- [2-(吡咯烷-1-基)-1 H-苯并咪唑-1-基]乙烷-与HBr反应形成1-one。

更新日期:2020-11-25
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