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

Xiaoming Ma; Suzhi Meng; Xiaofeng Zhang; Qiang Zhang; Shenghu Yan; Yue Zhang; Wei Zhang

doi:10.3762/bxiv.2020.28.v1

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

Xiaoming Ma ,
Suzhi Meng ,
Xiaofeng Zhang ,
Qiang Zhang ,
Shenghu Yan ,
Yue Zhang and
Wei Zhang

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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Read the peer-reviewed version of this preprint: https://doi.org/10.3762/bjoc.16.106

SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

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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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)