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Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides

[Image: see text] An N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aromatic aldehydes with N-substituted itaconimides has been developed. A delicate balance between the Stetter reaction and the competing isomerization of the itaconimide double bond has been achieved in this ope...

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Autores principales: Ahire, Milind M., Mhaske, Santosh B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644805/
https://www.ncbi.nlm.nih.gov/pubmed/31457257
http://dx.doi.org/10.1021/acsomega.7b01213
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author Ahire, Milind M.
Mhaske, Santosh B.
author_facet Ahire, Milind M.
Mhaske, Santosh B.
author_sort Ahire, Milind M.
collection PubMed
description [Image: see text] An N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aromatic aldehydes with N-substituted itaconimides has been developed. A delicate balance between the Stetter reaction and the competing isomerization of the itaconimide double bond has been achieved in this operationally simple reaction to afford valuable new succinimide derivatives containing 1,4 and 1,5 dicarbonyl scaffolds in good to excellent yields. The reaction tolerates variable substituents on both aldehydes and N-substituted itaconimides.
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spelling pubmed-66448052019-08-27 Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides Ahire, Milind M. Mhaske, Santosh B. ACS Omega [Image: see text] An N-heterocyclic carbene-catalyzed intermolecular Stetter reaction of aromatic aldehydes with N-substituted itaconimides has been developed. A delicate balance between the Stetter reaction and the competing isomerization of the itaconimide double bond has been achieved in this operationally simple reaction to afford valuable new succinimide derivatives containing 1,4 and 1,5 dicarbonyl scaffolds in good to excellent yields. The reaction tolerates variable substituents on both aldehydes and N-substituted itaconimides. American Chemical Society 2017-10-11 /pmc/articles/PMC6644805/ /pubmed/31457257 http://dx.doi.org/10.1021/acsomega.7b01213 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 Ahire, Milind M.
Mhaske, Santosh B.
Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides
title Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides
title_full Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides
title_fullStr Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides
title_full_unstemmed Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides
title_short Synthesis of Succinimide Derivatives by NHC-Catalyzed Stetter Reaction of Aromatic Aldehydes with N-Substituted Itaconimides
title_sort synthesis of succinimide derivatives by nhc-catalyzed stetter reaction of aromatic aldehydes with n-substituted itaconimides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644805/
https://www.ncbi.nlm.nih.gov/pubmed/31457257
http://dx.doi.org/10.1021/acsomega.7b01213
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