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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)....

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Detalles Bibliográficos
Autores principales: Wang, Zhuo, Zhao, Yuhan, Chen, Jiaxin, Chen, Mengyao, Li, Xuehan, Jiang, Ting, Liu, Fang, Yang, Xi, Sun, Yuanyuan, Zhu, Yanping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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.
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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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