Chinese Journal of Organic Chemistry >
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)
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
Xiang Wang , Ping Chen , Sanjun Zhi , Huayou Hu , Yuhe Kan , Guodong Tang , Zaichao Zhang . Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1241 -1245 . DOI: 10.6023/cjoc202008028
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