Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization

An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed—a two-step Michael addition–cyclization condensation step leading to int...

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Detalles Bibliográficos
Autores principales: Yang, Mingming, Jian, Yajun, Zhang, Weiqiang, Sun, Huaming, Zhang, Guofang, Wang, Yanyan, Gao, Ziwei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9044151/
https://www.ncbi.nlm.nih.gov/pubmed/35493239
http://dx.doi.org/10.1039/d1ra06976d
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author Yang, Mingming
Jian, Yajun
Zhang, Weiqiang
Sun, Huaming
Zhang, Guofang
Wang, Yanyan
Gao, Ziwei
author_facet Yang, Mingming
Jian, Yajun
Zhang, Weiqiang
Sun, Huaming
Zhang, Guofang
Wang, Yanyan
Gao, Ziwei
author_sort Yang, Mingming
collection PubMed
description An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed—a two-step Michael addition–cyclization condensation step leading to intermediate 1,5-benzothiazepine catalyzed by zirconocene amino acid complex Cp(2)Zr(η(1)-C(9)H(10)NO(2))(2), followed by I(2)-mediated desulfurative step.
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spelling pubmed-90441512022-04-28 Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization Yang, Mingming Jian, Yajun Zhang, Weiqiang Sun, Huaming Zhang, Guofang Wang, Yanyan Gao, Ziwei RSC Adv Chemistry An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed—a two-step Michael addition–cyclization condensation step leading to intermediate 1,5-benzothiazepine catalyzed by zirconocene amino acid complex Cp(2)Zr(η(1)-C(9)H(10)NO(2))(2), followed by I(2)-mediated desulfurative step. The Royal Society of Chemistry 2021-12-06 /pmc/articles/PMC9044151/ /pubmed/35493239 http://dx.doi.org/10.1039/d1ra06976d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Yang, Mingming
Jian, Yajun
Zhang, Weiqiang
Sun, Huaming
Zhang, Guofang
Wang, Yanyan
Gao, Ziwei
Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization
title Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization
title_full Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization
title_fullStr Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization
title_full_unstemmed Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization
title_short Synthesis of quinolines via sequential addition and I(2)-mediated desulfurative cyclization
title_sort synthesis of quinolines via sequential addition and i(2)-mediated desulfurative cyclization
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9044151/
https://www.ncbi.nlm.nih.gov/pubmed/35493239
http://dx.doi.org/10.1039/d1ra06976d
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AT zhangguofang synthesisofquinolinesviasequentialadditionandi2mediateddesulfurativecyclization
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