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

ABSTRACT: 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.

SUBMITTER: Pan F 

PROVIDER: S-EPMC10184271 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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

Pan Feng F   Li Haohu H   Wang Xiaohua X   Luo Liwen L   Lin Yanfei Y   Yu Qingkai Q   Xie Wenlin W   Zhang Lianpeng L  

RSC advances 20230515 20

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 <i>N</i>-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.  ...[more]

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