Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3180-3191.DOI: 10.6023/cjoc202103034 Previous Articles     Next Articles



马蔚青, 韩莹*(), 孙晶, 颜朝国*()   

  1. 扬州大学化学化工学院 江苏扬州 225002
  • 收稿日期:2021-03-21 修回日期:2021-04-14 发布日期:2021-05-14
  • 通讯作者: 韩莹, 颜朝国
  • 基金资助:
    国家自然科学基金(21572196); 江苏高校优势学科建设工程资助项目

Three-Component Reaction for Efficient Synthesis of Functionalized Spiro[cyclopentane-1,3'-indolines]

Weiqing Ma, Ying Han(), Jin Sun, Chaoguo Yan()   

  1. College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002
  • Received:2021-03-21 Revised:2021-04-14 Published:2021-05-14
  • Contact: Ying Han, Chaoguo Yan
  • Supported by:
    National Natural Science Foundation of China(21572196); Priority Academic Program Development of Jiangsu Higher Education Institutions

The three-component reaction of alkylisocyanide, dialkyl acetylenedicarboxylate (alkyl propiolate) and 3-phenacylideneoxindole in refluxing toluene afforded the functionalized spiro[cyclopentane-1,3'-indolines] in satisfactory yields. However, the similar reaction of 3-phenacylideneoxindoles with unsubstituted NH group resulted in spiro[cyclopentane-1,3'-indolines] with additional aza-buta-1,3-diene scaffold. On the other hand, the three-component reactions with 3-arylideneoxindolin- 2-ones only gave 2-(2-oxoindolin-1-yl)-3-((alkylimino)methylene)succinates. It was also interesting to find that the reaction of free amino group in two kinds of functionalized 3-methyleneoxindoles with alkylisocyanide and dialkyl acetylenedicarboxylate selectively gave C2-substituted 1-aza-buta-1,3-diene (C=C—C=NR) or C4-substituted 1-aza-buta-1,2-diene (C—C=C=NR) scaffold in the molecules.

Key words: isocyanide, dialkyl acetylenedicarboxylate, 3-phenacylideneoxindole, spiro[cyclopentane-1,3'-indoline], multicomponent reaction