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Direct Minisci-Type C–H Amidation of Purine Bases

[Image: see text] A method for the C–H carboxyamidation of purines has been developed that is capable of directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for th...

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Autores principales: Mooney, David T., Moore, Peter R., Lee, Ai-Lan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641672/
https://www.ncbi.nlm.nih.gov/pubmed/36285836
http://dx.doi.org/10.1021/acs.orglett.2c03206
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author Mooney, David T.
Moore, Peter R.
Lee, Ai-Lan
author_facet Mooney, David T.
Moore, Peter R.
Lee, Ai-Lan
author_sort Mooney, David T.
collection PubMed
description [Image: see text] A method for the C–H carboxyamidation of purines has been developed that is capable of directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for the direct C–H amidation of a wide range of purines: xanthine, guanine, and adenine structures, including guanosine- and adenosine-type nucleosides. The Minisci-type reaction is also metal-free, cheap, operationally simple, scalable, and applicable to late-stage functionalizations of biologically important molecules.
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spelling pubmed-96416722022-11-15 Direct Minisci-Type C–H Amidation of Purine Bases Mooney, David T. Moore, Peter R. Lee, Ai-Lan Org Lett [Image: see text] A method for the C–H carboxyamidation of purines has been developed that is capable of directly installing primary, secondary, and tertiary amides. Previous Minisci-type investigations on purines were limited to alkylations and arylations. Herein, we present the first method for the direct C–H amidation of a wide range of purines: xanthine, guanine, and adenine structures, including guanosine- and adenosine-type nucleosides. The Minisci-type reaction is also metal-free, cheap, operationally simple, scalable, and applicable to late-stage functionalizations of biologically important molecules. American Chemical Society 2022-10-26 2022-11-04 /pmc/articles/PMC9641672/ /pubmed/36285836 http://dx.doi.org/10.1021/acs.orglett.2c03206 Text en © 2022 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 Mooney, David T.
Moore, Peter R.
Lee, Ai-Lan
Direct Minisci-Type C–H Amidation of Purine Bases
title Direct Minisci-Type C–H Amidation of Purine Bases
title_full Direct Minisci-Type C–H Amidation of Purine Bases
title_fullStr Direct Minisci-Type C–H Amidation of Purine Bases
title_full_unstemmed Direct Minisci-Type C–H Amidation of Purine Bases
title_short Direct Minisci-Type C–H Amidation of Purine Bases
title_sort direct minisci-type c–h amidation of purine bases
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9641672/
https://www.ncbi.nlm.nih.gov/pubmed/36285836
http://dx.doi.org/10.1021/acs.orglett.2c03206
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