An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl

The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corres...

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Autores principales: Wu, Wengang, Yi, Jun, Xu, Huipeng, Li, Shuangjun, Yuan, Rongxin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6480081/
https://www.ncbi.nlm.nih.gov/pubmed/30934862
http://dx.doi.org/10.3390/molecules24071234
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author Wu, Wengang
Yi, Jun
Xu, Huipeng
Li, Shuangjun
Yuan, Rongxin
author_facet Wu, Wengang
Yi, Jun
Xu, Huipeng
Li, Shuangjun
Yuan, Rongxin
author_sort Wu, Wengang
collection PubMed
description The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C((acyl))–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.
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spelling pubmed-64800812019-04-30 An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl Wu, Wengang Yi, Jun Xu, Huipeng Li, Shuangjun Yuan, Rongxin Molecules Communication The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C((acyl))–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields. MDPI 2019-03-29 /pmc/articles/PMC6480081/ /pubmed/30934862 http://dx.doi.org/10.3390/molecules24071234 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Wu, Wengang
Yi, Jun
Xu, Huipeng
Li, Shuangjun
Yuan, Rongxin
An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
title An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
title_full An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
title_fullStr An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
title_full_unstemmed An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
title_short An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl
title_sort efficient, one-pot transamidation of 8-aminoquinoline amides activated by tertiary-butyloxycarbonyl
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6480081/
https://www.ncbi.nlm.nih.gov/pubmed/30934862
http://dx.doi.org/10.3390/molecules24071234
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