An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction

An oxidant-free and highly efficient synthesis of phenolic quinazolin-4(3H)-ones was achieved by simply stirring a mixture of 2-aminobenzamides, sulfonyl azides, and terminal alkynes. The intermediate N-sulfonylketenimine underwent two nucleophilic additions and the sulfonyl group eliminated through...

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Autores principales: He, Yueling, Yang, Zhongtao, Luo, Danyang, Luo, Xiai, Chen, Xiaodong, Yang, Weiguang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420183/
https://www.ncbi.nlm.nih.gov/pubmed/37570705
http://dx.doi.org/10.3390/molecules28155734
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author He, Yueling
Yang, Zhongtao
Luo, Danyang
Luo, Xiai
Chen, Xiaodong
Yang, Weiguang
author_facet He, Yueling
Yang, Zhongtao
Luo, Danyang
Luo, Xiai
Chen, Xiaodong
Yang, Weiguang
author_sort He, Yueling
collection PubMed
description An oxidant-free and highly efficient synthesis of phenolic quinazolin-4(3H)-ones was achieved by simply stirring a mixture of 2-aminobenzamides, sulfonyl azides, and terminal alkynes. The intermediate N-sulfonylketenimine underwent two nucleophilic additions and the sulfonyl group eliminated through the power of aromatization. The natural product 2-(4-hydroxybenzyl)quinazolin-4(3H)-one can be synthesized on a large scale under mild conditions with this method.
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spelling pubmed-104201832023-08-12 An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction He, Yueling Yang, Zhongtao Luo, Danyang Luo, Xiai Chen, Xiaodong Yang, Weiguang Molecules Article An oxidant-free and highly efficient synthesis of phenolic quinazolin-4(3H)-ones was achieved by simply stirring a mixture of 2-aminobenzamides, sulfonyl azides, and terminal alkynes. The intermediate N-sulfonylketenimine underwent two nucleophilic additions and the sulfonyl group eliminated through the power of aromatization. The natural product 2-(4-hydroxybenzyl)quinazolin-4(3H)-one can be synthesized on a large scale under mild conditions with this method. MDPI 2023-07-28 /pmc/articles/PMC10420183/ /pubmed/37570705 http://dx.doi.org/10.3390/molecules28155734 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
He, Yueling
Yang, Zhongtao
Luo, Danyang
Luo, Xiai
Chen, Xiaodong
Yang, Weiguang
An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction
title An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction
title_full An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction
title_fullStr An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction
title_full_unstemmed An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction
title_short An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction
title_sort oxidant-free and mild strategy for quinazolin-4(3h)-one synthesis via cuaac/ring cleavage reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10420183/
https://www.ncbi.nlm.nih.gov/pubmed/37570705
http://dx.doi.org/10.3390/molecules28155734
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