Traceless Redox-Annulations of Alicyclic Amines

Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-(nitromethyl)benzaldehyde. Benzoic acid acts as a promoter in these reactions, which involve concurrent amine α-C–H bond and N–H bond functionalization. Subsequent removal of the nitro group provides access to...

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Autores principales: Rickertsen, Dillon R. L., Ma, Longle, Paul, Anirudra, Abboud, Khalil A., Seidel, Daniel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8318209/
https://www.ncbi.nlm.nih.gov/pubmed/34327302
http://dx.doi.org/10.1055/s-0040-1706004
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author Rickertsen, Dillon R. L.
Ma, Longle
Paul, Anirudra
Abboud, Khalil A.
Seidel, Daniel
author_facet Rickertsen, Dillon R. L.
Ma, Longle
Paul, Anirudra
Abboud, Khalil A.
Seidel, Daniel
author_sort Rickertsen, Dillon R. L.
collection PubMed
description Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-(nitromethyl)benzaldehyde. Benzoic acid acts as a promoter in these reactions, which involve concurrent amine α-C–H bond and N–H bond functionalization. Subsequent removal of the nitro group provides access to tetrahydroprotoberberines not accessible via typical redox-annulations. Also reported are decarboxylative annulations of ortho-(nitromethyl)benzaldehyde with proline and pipecolic acid.
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spelling pubmed-83182092021-07-28 Traceless Redox-Annulations of Alicyclic Amines Rickertsen, Dillon R. L. Ma, Longle Paul, Anirudra Abboud, Khalil A. Seidel, Daniel SynOpen Article Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-(nitromethyl)benzaldehyde. Benzoic acid acts as a promoter in these reactions, which involve concurrent amine α-C–H bond and N–H bond functionalization. Subsequent removal of the nitro group provides access to tetrahydroprotoberberines not accessible via typical redox-annulations. Also reported are decarboxylative annulations of ortho-(nitromethyl)benzaldehyde with proline and pipecolic acid. 2020-12-16 2020 /pmc/articles/PMC8318209/ /pubmed/34327302 http://dx.doi.org/10.1055/s-0040-1706004 Text en https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
spellingShingle Article
Rickertsen, Dillon R. L.
Ma, Longle
Paul, Anirudra
Abboud, Khalil A.
Seidel, Daniel
Traceless Redox-Annulations of Alicyclic Amines
title Traceless Redox-Annulations of Alicyclic Amines
title_full Traceless Redox-Annulations of Alicyclic Amines
title_fullStr Traceless Redox-Annulations of Alicyclic Amines
title_full_unstemmed Traceless Redox-Annulations of Alicyclic Amines
title_short Traceless Redox-Annulations of Alicyclic Amines
title_sort traceless redox-annulations of alicyclic amines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8318209/
https://www.ncbi.nlm.nih.gov/pubmed/34327302
http://dx.doi.org/10.1055/s-0040-1706004
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AT paulanirudra tracelessredoxannulationsofalicyclicamines
AT abboudkhalila tracelessredoxannulationsofalicyclicamines
AT seideldaniel tracelessredoxannulationsofalicyclicamines

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