利用三组分串联反应合成3-苯并[d]咪唑啉取代的吡喃并[3,2-c]色烯-2-酮衍生物
收稿日期: 2020-08-16
修回日期: 2020-09-28
网络出版日期: 2020-11-19
基金资助
国家自然科学基金(51403073); 国家自然科学基金(21601061); 江苏省高等学校自然科学研究基金(16KJB150006); 江苏省低维材料化学重点实验室开放基金(JSKC15145)
Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction
Received date: 2020-08-16
Revised date: 2020-09-28
Online published: 2020-11-19
Supported by
National Natural Science Foundation of China(51403073); National Natural Science Foundation of China(21601061); Natural Science Foundation of the Jiangsu Higher Education Institutions of China(16KJB150006); Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials(JSKC15145)
苯并咪唑和香豆素并吡喃衍生物具有重要的生物活性. 目前制备兼具苯并咪唑和香豆素并吡喃骨架的杂环化合物尚缺乏有效的方法. 报道了在醋酸促进下芳醛、2-氰甲基苯并咪唑和4-羟基香豆素的三组分串联环化反应, 合成了一系列3-苯并咪唑啉取代的吡喃并[3,2-c]色烯-2-酮衍生物, 收率为58%~84%. 该反应采用兼容各种官能化的芳醛, 如氯、溴、氰基、甲氧基取代的芳醛以及杂芳醛等, 且醋酸既为溶剂又为布朗斯特酸催化剂, 为含氧、含氮杂环的合成提供了一种有效的策略.
关键词： 吡喃并[3,2-c]色烯-2-酮; 三组分反应; 香豆素; 环化; 吡喃酮
王翔 , 陈平 , 支三军 , 胡华友 , 阚玉和 , 唐果东 , 张载超 . 利用三组分串联反应合成3-苯并[d]咪唑啉取代的吡喃并[3,2-c]色烯-2-酮衍生物[J]. 有机化学, 2021 , 41(3) : 1241 -1245 . DOI: 10.6023/cjoc202008028
Both benzimidazoles and pyranochromenes exhibit a variety of important biological activities. However, the effective preparation of compounds incorporating both pyranochromene and benzoimidazole moieties is very rare. In this paper, a HOAc-promoted three-component annulation reaction of aromatic aldehydes with 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and 4-hydroxy-2H-chromen-2-one is reported, leading to the formation of a series of 3-benzo[d]imidazol-2(3H)-ylidene substituted pyrano[3,2-c]chromen-2-ones in 58%~84% yields. The current reaction could tolerate aromatic aldehydes with diverse functional groups such as chloro, bromo, cyano, methoxy and heteroaryl aldehydes, and HOAc served as the reaction media as well as the Br?nsted acid catalyst, thereby providing an effective synthetic method for the construction ofN,O-containing heterocyles.
Key words： pyrano[3,2-c]chromen-2-one; three-component reaction; coumarins; annulation; pyrones
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