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

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

Beilstein Arch. 2020, 202028. https://doi.org/10.3762/bxiv.2020.28.v1

Published 16 Mar 2020

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Abstract

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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