Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy

[Image: see text] A simple method for the C-4 alkylation of isoquinolines is described using benzoic acid as a nucleophilic reagent and vinyl ketones as an electrophile. The reaction shows tolerance for substitution at C-3, and C-5–C-8 positions as well as allowing some variation of the vinyl ketone...

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Autores principales: Day, Aaron J., Jenkins, Timothy C., Kischkewitz, Marvin, Christensen, Kirsten E., Poole, Darren L., Donohoe, Timothy J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9903316/
https://www.ncbi.nlm.nih.gov/pubmed/36688518
http://dx.doi.org/10.1021/acs.orglett.2c04149
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author Day, Aaron J.
Jenkins, Timothy C.
Kischkewitz, Marvin
Christensen, Kirsten E.
Poole, Darren L.
Donohoe, Timothy J.
author_facet Day, Aaron J.
Jenkins, Timothy C.
Kischkewitz, Marvin
Christensen, Kirsten E.
Poole, Darren L.
Donohoe, Timothy J.
author_sort Day, Aaron J.
collection PubMed
description [Image: see text] A simple method for the C-4 alkylation of isoquinolines is described using benzoic acid as a nucleophilic reagent and vinyl ketones as an electrophile. The reaction shows tolerance for substitution at C-3, and C-5–C-8 positions as well as allowing some variation of the vinyl ketone electrophiles. The products contain a carbonyl that can act as a synthetic handle for further manipulations giving esters, amines, or simple alkyl products.
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spelling pubmed-99033162023-02-08 Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy Day, Aaron J. Jenkins, Timothy C. Kischkewitz, Marvin Christensen, Kirsten E. Poole, Darren L. Donohoe, Timothy J. Org Lett [Image: see text] A simple method for the C-4 alkylation of isoquinolines is described using benzoic acid as a nucleophilic reagent and vinyl ketones as an electrophile. The reaction shows tolerance for substitution at C-3, and C-5–C-8 positions as well as allowing some variation of the vinyl ketone electrophiles. The products contain a carbonyl that can act as a synthetic handle for further manipulations giving esters, amines, or simple alkyl products. American Chemical Society 2023-01-23 /pmc/articles/PMC9903316/ /pubmed/36688518 http://dx.doi.org/10.1021/acs.orglett.2c04149 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Day, Aaron J.
Jenkins, Timothy C.
Kischkewitz, Marvin
Christensen, Kirsten E.
Poole, Darren L.
Donohoe, Timothy J.
Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy
title Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy
title_full Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy
title_fullStr Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy
title_full_unstemmed Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy
title_short Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy
title_sort metal and activating group free c-4 alkylation of isoquinolines via a temporary dearomatization strategy
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9903316/
https://www.ncbi.nlm.nih.gov/pubmed/36688518
http://dx.doi.org/10.1021/acs.orglett.2c04149
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