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One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions
A practical method was developed for the convenient synthesis of isoxazole-fused tricyclic quinazoline alkaloids. This procedure accesses diverse isoxazole-fused tricyclic quinazoline alkaloids and their derivatives via intramolecular cycloaddition of methyl azaarenes with tert-butyl nitrite (TBN)....
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10057414/ https://www.ncbi.nlm.nih.gov/pubmed/36985760 http://dx.doi.org/10.3390/molecules28062787 |
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author | Wang, Zhuo Zhao, Yuhan Chen, Jiaxin Chen, Mengyao Li, Xuehan Jiang, Ting Liu, Fang Yang, Xi Sun, Yuanyuan Zhu, Yanping |
author_facet | Wang, Zhuo Zhao, Yuhan Chen, Jiaxin Chen, Mengyao Li, Xuehan Jiang, Ting Liu, Fang Yang, Xi Sun, Yuanyuan Zhu, Yanping |
author_sort | Wang, Zhuo |
collection | PubMed |
description | A practical method was developed for the convenient synthesis of isoxazole-fused tricyclic quinazoline alkaloids. This procedure accesses diverse isoxazole-fused tricyclic quinazoline alkaloids and their derivatives via intramolecular cycloaddition of methyl azaarenes with tert-butyl nitrite (TBN). In this method, TBN acts as the radical initiator and the source of N–O. Moreover, this protocol forms new C–N, C–C, and C–O bonds via sequence nitration and annulation in a one-pot process with broad substrate scope and functionalization of natural products. |
format | Online Article Text |
id | pubmed-10057414 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-100574142023-03-30 One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions Wang, Zhuo Zhao, Yuhan Chen, Jiaxin Chen, Mengyao Li, Xuehan Jiang, Ting Liu, Fang Yang, Xi Sun, Yuanyuan Zhu, Yanping Molecules Article A practical method was developed for the convenient synthesis of isoxazole-fused tricyclic quinazoline alkaloids. This procedure accesses diverse isoxazole-fused tricyclic quinazoline alkaloids and their derivatives via intramolecular cycloaddition of methyl azaarenes with tert-butyl nitrite (TBN). In this method, TBN acts as the radical initiator and the source of N–O. Moreover, this protocol forms new C–N, C–C, and C–O bonds via sequence nitration and annulation in a one-pot process with broad substrate scope and functionalization of natural products. MDPI 2023-03-20 /pmc/articles/PMC10057414/ /pubmed/36985760 http://dx.doi.org/10.3390/molecules28062787 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 Wang, Zhuo Zhao, Yuhan Chen, Jiaxin Chen, Mengyao Li, Xuehan Jiang, Ting Liu, Fang Yang, Xi Sun, Yuanyuan Zhu, Yanping One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions |
title | One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions |
title_full | One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions |
title_fullStr | One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions |
title_full_unstemmed | One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions |
title_short | One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions |
title_sort | one-pot synthesis of isoxazole-fused tricyclic quinazoline alkaloid derivatives via intramolecular cycloaddition of propargyl-substituted methyl azaarenes under metal-free conditions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10057414/ https://www.ncbi.nlm.nih.gov/pubmed/36985760 http://dx.doi.org/10.3390/molecules28062787 |
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