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Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

  • Xiaoming Ma
  • , Suzhi Meng
  • , Xiaofeng Zhang
  • , Qiang Zhang
  • , Shenghu Yan
  • , Yue Zhang
  • , Wei Zhang
  • Changzhou University
  • University of Massachusetts Boston
  • Harvard University
  • Suzhou University of Science and Technology

Research output: Contribution to journal › Article › peer-review

Abstract

Two kinds of [3 + 2] cycloaddition intermediates generated from the three-component reactions of 2-bromobenzaldehydes and maleimides with amino esters or amino acids were used for a one-pot N-allylation and intramolecular Heck reactions to form pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines. The multicomponent reaction was combined with one-pot reactions to make a synthetic method with good pot, atom and step economy. MeCN was used as a preferable green solvent for the reactions.

Original languageEnglish
Pages (from-to)1225-1233
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
StatePublished - Jun 4 2020

ASJC Scopus Subject Areas

  • Organic Chemistry

Keywords

  • Heck reaction
  • Hexahydropyrrolo[2,1-a]isoquinoline
  • One-pot reactions
  • [3 + 2] cycloaddition

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