Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process

The selective and controllable construction of spio-tricyclic skeletons through visible light promoted radical cyclization still remains challenging. Herein, a general and convenient protocol for the blue light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamid...

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Detalles Bibliográficos
Autores principales: Pan, Feng, Li, Haohu, Wang, Xiaohua, Luo, Liwen, Lin, Yanfei, Yu, Qingkai, Xie, Wenlin, Zhang, Lianpeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10184271/
https://www.ncbi.nlm.nih.gov/pubmed/37197573
http://dx.doi.org/10.1039/d3ra02247a
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author Pan, Feng
Li, Haohu
Wang, Xiaohua
Luo, Liwen
Lin, Yanfei
Yu, Qingkai
Xie, Wenlin
Zhang, Lianpeng
author_facet Pan, Feng
Li, Haohu
Wang, Xiaohua
Luo, Liwen
Lin, Yanfei
Yu, Qingkai
Xie, Wenlin
Zhang, Lianpeng
author_sort Pan, Feng
collection PubMed
description The selective and controllable construction of spio-tricyclic skeletons through visible light promoted radical cyclization still remains challenging. Herein, a general and convenient protocol for the blue light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamides with thiophenols under metal-free conditions was developed. In this protocol, commercially available hydrochloric acid was employed as the cheap promoter and air as the sustainable oxidant. In addition, many functional groups tolerate the reaction conditions and produce a series of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones.
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spelling pubmed-101842712023-05-16 Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process Pan, Feng Li, Haohu Wang, Xiaohua Luo, Liwen Lin, Yanfei Yu, Qingkai Xie, Wenlin Zhang, Lianpeng RSC Adv Chemistry The selective and controllable construction of spio-tricyclic skeletons through visible light promoted radical cyclization still remains challenging. Herein, a general and convenient protocol for the blue light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamides with thiophenols under metal-free conditions was developed. In this protocol, commercially available hydrochloric acid was employed as the cheap promoter and air as the sustainable oxidant. In addition, many functional groups tolerate the reaction conditions and produce a series of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones. The Royal Society of Chemistry 2023-05-15 /pmc/articles/PMC10184271/ /pubmed/37197573 http://dx.doi.org/10.1039/d3ra02247a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Pan, Feng
Li, Haohu
Wang, Xiaohua
Luo, Liwen
Lin, Yanfei
Yu, Qingkai
Xie, Wenlin
Zhang, Lianpeng
Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
title Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
title_full Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
title_fullStr Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
title_full_unstemmed Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
title_short Synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
title_sort synthesis of sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones: blue light promoted radical cyclization process
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10184271/
https://www.ncbi.nlm.nih.gov/pubmed/37197573
http://dx.doi.org/10.1039/d3ra02247a
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