一种新型多组分反应合成咪唑并[4,5-g]-喹唑啉。

A novel multi-component reaction to imidazo[4,5-g]-quinazolines.

机构信息

Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China.

出版信息

Molecules. 2013 May 16;18(5):5697-705. doi: 10.3390/molecules18055697.

DOI:10.3390/molecules18055697

PMID:23681055

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6269788/

Abstract

The trace impurities discovered after extended storage of a 5-amino- benzimidazole library were determined as imidazo[4,5-g]quinazoline derivatives by extensive spectroscopic data analysis. The formation of this highly aromatic heterocyclic ring involved a novel multi-component reaction, using which several novel compounds were prepared. Its mechanism was deduced as a cascade of chemical transformations, including the formation of a Schiff's base, intramolecular hetero-Diels-Alder reaction, defluorination and dehydrogenation.

摘要

经长时间储存的 5-氨基苯并咪唑文库中发现的痕量杂质，通过广泛的光谱数据分析被确定为咪唑并[4,5-g]喹唑啉衍生物。这个高度芳环杂环的形成涉及到一个新颖的多组分反应，利用该反应制备了几种新型化合物。其反应机理被推断为一系列的化学反应，包括席夫碱的形成、分子内杂 Diels-Alder 反应、脱氟和脱氢。