Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide

[Image: see text] The base-promoted cycloaddition reaction of N-cyanomethylisoquinolinium chloride with 2-arylidene-1,3-indanediones in dry tetrahydrofuran resulted in the expected spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline] derivatives. However, the triethylamine-promoted three-component reaction...

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Autores principales: Shi, Rong-Guo, Sun, Jing, Yan, Chao-Guo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645381/
https://www.ncbi.nlm.nih.gov/pubmed/31457339
http://dx.doi.org/10.1021/acsomega.7b01391
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author Shi, Rong-Guo
Sun, Jing
Yan, Chao-Guo
author_facet Shi, Rong-Guo
Sun, Jing
Yan, Chao-Guo
author_sort Shi, Rong-Guo
collection PubMed
description [Image: see text] The base-promoted cycloaddition reaction of N-cyanomethylisoquinolinium chloride with 2-arylidene-1,3-indanediones in dry tetrahydrofuran resulted in the expected spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline] derivatives. However, the triethylamine-promoted three-component reaction of N-cyanomethylisoquinolinium chloride, aromatic aldehydes, and two molecules of 1,3-indanediones in acetonitrile afforded unique spiro[benzo[f]imidazo[5,1,2-cd]indolizine-4,2′-indene] derivatives in satisfactory yields through tandem double [3 + 2] cycloaddition reactions.
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spelling pubmed-66453812019-08-27 Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide Shi, Rong-Guo Sun, Jing Yan, Chao-Guo ACS Omega [Image: see text] The base-promoted cycloaddition reaction of N-cyanomethylisoquinolinium chloride with 2-arylidene-1,3-indanediones in dry tetrahydrofuran resulted in the expected spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline] derivatives. However, the triethylamine-promoted three-component reaction of N-cyanomethylisoquinolinium chloride, aromatic aldehydes, and two molecules of 1,3-indanediones in acetonitrile afforded unique spiro[benzo[f]imidazo[5,1,2-cd]indolizine-4,2′-indene] derivatives in satisfactory yields through tandem double [3 + 2] cycloaddition reactions. American Chemical Society 2017-11-13 /pmc/articles/PMC6645381/ /pubmed/31457339 http://dx.doi.org/10.1021/acsomega.7b01391 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Shi, Rong-Guo
Sun, Jing
Yan, Chao-Guo
Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide
title Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide
title_full Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide
title_fullStr Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide
title_full_unstemmed Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide
title_short Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide
title_sort tandem double [3 + 2] cycloaddition reactions at both c-1 and c-3 atoms of n-cyanomethylisoquinolinium ylide
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645381/
https://www.ncbi.nlm.nih.gov/pubmed/31457339
http://dx.doi.org/10.1021/acsomega.7b01391
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AT yanchaoguo tandemdouble32cycloadditionreactionsatbothc1andc3atomsofncyanomethylisoquinoliniumylide

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