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

  1. Xiaoming MaORCID Logo,
  2. Suzhi Meng,
  3. Xiaofeng Zhang,
  4. Qiang Zhang,
  5. Shenghu Yan,
  6. Yue Zhang and
  7. Wei ZhangORCID Logo

Submitting author affiliation: University of Massachusetts Boston, Boston, United States

Beilstein Arch. 2020, 202028.

Published 16 Mar 2020

  • Preprint


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

Keywords: [3+2] cycloaddition; Heck reaction; hexahydropyrrolo[2,1-a]isoquinoline, one-pot reactions

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Ma, X.; Meng, S.; Zhang, X.; Zhang, Q.; Yan, S.; Zhang, Y.; Zhang, W. Beilstein Arch. 2020, 202028. doi:10.3762/bxiv.2020.28.v1

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