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3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides

An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza...

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Autores principales: Zhao, Jian-Qiang, Wang, Wen-Jie, Zhou, Shun, Xiao, Qi-Lin, Xue, Xi-Sha, Zhang, Yan-Ping, You, Yong, Wang, Zhen-Hua, Yuan, Wei-Cheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10384903/
https://www.ncbi.nlm.nih.gov/pubmed/37513401
http://dx.doi.org/10.3390/molecules28145529
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author Zhao, Jian-Qiang
Wang, Wen-Jie
Zhou, Shun
Xiao, Qi-Lin
Xue, Xi-Sha
Zhang, Yan-Ping
You, Yong
Wang, Zhen-Hua
Yuan, Wei-Cheng
author_facet Zhao, Jian-Qiang
Wang, Wen-Jie
Zhou, Shun
Xiao, Qi-Lin
Xue, Xi-Sha
Zhang, Yan-Ping
You, Yong
Wang, Zhen-Hua
Yuan, Wei-Cheng
author_sort Zhao, Jian-Qiang
collection PubMed
description An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent N-centered nucleophiles to react with ortho-hydrophenyl p-QMs for construction of various N-diarylmethylindoles.
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spelling pubmed-103849032023-07-30 3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides Zhao, Jian-Qiang Wang, Wen-Jie Zhou, Shun Xiao, Qi-Lin Xue, Xi-Sha Zhang, Yan-Ping You, Yong Wang, Zhen-Hua Yuan, Wei-Cheng Molecules Article An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent N-centered nucleophiles to react with ortho-hydrophenyl p-QMs for construction of various N-diarylmethylindoles. MDPI 2023-07-20 /pmc/articles/PMC10384903/ /pubmed/37513401 http://dx.doi.org/10.3390/molecules28145529 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhao, Jian-Qiang
Wang, Wen-Jie
Zhou, Shun
Xiao, Qi-Lin
Xue, Xi-Sha
Zhang, Yan-Ping
You, Yong
Wang, Zhen-Hua
Yuan, Wei-Cheng
3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides
title 3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides
title_full 3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides
title_fullStr 3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides
title_full_unstemmed 3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides
title_short 3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides
title_sort 3-nitroindoles serving as n-centered nucleophiles for aza-1,6-michael addition to para-quinone methides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10384903/
https://www.ncbi.nlm.nih.gov/pubmed/37513401
http://dx.doi.org/10.3390/molecules28145529
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