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

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]isoquinol...

Descripción completa

Detalles Bibliográficos
Autores principales: Ma, Xiaoming, Meng, Suzhi, Zhang, Xiaofeng, Zhang, Qiang, Yan, Shenghu, Zhang, Yue, Zhang, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277624/
https://www.ncbi.nlm.nih.gov/pubmed/32550934
http://dx.doi.org/10.3762/bjoc.16.106
_version_ 1783543161713328128
author Ma, Xiaoming
Meng, Suzhi
Zhang, Xiaofeng
Zhang, Qiang
Yan, Shenghu
Zhang, Yue
Zhang, Wei
author_facet Ma, Xiaoming
Meng, Suzhi
Zhang, Xiaofeng
Zhang, Qiang
Yan, Shenghu
Zhang, Yue
Zhang, Wei
author_sort Ma, Xiaoming
collection PubMed
description 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.
format Online
Article
Text
id pubmed-7277624
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-72776242020-06-17 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 Ma, Xiaoming Meng, Suzhi Zhang, Xiaofeng Zhang, Qiang Yan, Shenghu Zhang, Yue Zhang, Wei Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2020-06-04 /pmc/articles/PMC7277624/ /pubmed/32550934 http://dx.doi.org/10.3762/bjoc.16.106 Text en Copyright © 2020, Ma et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Ma, Xiaoming
Meng, Suzhi
Zhang, Xiaofeng
Zhang, Qiang
Yan, Shenghu
Zhang, Yue
Zhang, Wei
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277624/
https://www.ncbi.nlm.nih.gov/pubmed/32550934
http://dx.doi.org/10.3762/bjoc.16.106
work_keys_str_mv AT maxiaoming synthesisofpyrrolidinedionefusedhexahydropyrrolo21aisoquinolinesviathreecomponent32cycloadditionfollowedbyonepotnallylationandintramolecularheckreactions
AT mengsuzhi synthesisofpyrrolidinedionefusedhexahydropyrrolo21aisoquinolinesviathreecomponent32cycloadditionfollowedbyonepotnallylationandintramolecularheckreactions
AT zhangxiaofeng synthesisofpyrrolidinedionefusedhexahydropyrrolo21aisoquinolinesviathreecomponent32cycloadditionfollowedbyonepotnallylationandintramolecularheckreactions
AT zhangqiang synthesisofpyrrolidinedionefusedhexahydropyrrolo21aisoquinolinesviathreecomponent32cycloadditionfollowedbyonepotnallylationandintramolecularheckreactions
AT yanshenghu synthesisofpyrrolidinedionefusedhexahydropyrrolo21aisoquinolinesviathreecomponent32cycloadditionfollowedbyonepotnallylationandintramolecularheckreactions
AT zhangyue synthesisofpyrrolidinedionefusedhexahydropyrrolo21aisoquinolinesviathreecomponent32cycloadditionfollowedbyonepotnallylationandintramolecularheckreactions
AT zhangwei synthesisofpyrrolidinedionefusedhexahydropyrrolo21aisoquinolinesviathreecomponent32cycloadditionfollowedbyonepotnallylationandintramolecularheckreactions

Ejemplares similares