Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1241-1245.DOI: 10.6023/cjoc202008028 Previous Articles     Next Articles



王翔1,*(), 陈平1, 支三军1, 胡华友1, 阚玉和1, 唐果东1, 张载超1,*()   

  1. 1 淮阴师范学院化学化工学院 江苏省低维材料化学重点实验室 淮安 223300
  • 收稿日期:2020-08-16 修回日期:2020-09-28 发布日期:2020-11-19
  • 通讯作者: 王翔, 张载超
  • 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

Xiang Wang1,*(), Ping Chen1, Sanjun Zhi1, Huayou Hu1, Yuhe Kan1, Guodong Tang1, Zaichao Zhang1,*()   

  1. 1 Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300
  • Received:2020-08-16 Revised:2020-09-28 Published:2020-11-19
  • Contact: Xiang Wang, Zaichao Zhang
  • About author:
    * Corresponding authors. E-mail: ;
  • 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