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Synlett 2022; 33(17): 1733-1738
DOI: 10.1055/a-1914-1722
letter

Photoinduced Tandem Cyclization of Alkynes with Phenylsulfinic Acids: Access to Sulfone-Substituted Dioxodibenzothiazepines or Dibenzazepines

Shiliu Chen
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry & Environmental Science Hebei University, Baoding, Hebei 071002, P. R. of China
,
Qinqin Yan
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry & Environmental Science Hebei University, Baoding, Hebei 071002, P. R. of China
,
Jie Fan
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry & Environmental Science Hebei University, Baoding, Hebei 071002, P. R. of China
,
Lijun Li∗
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry & Environmental Science Hebei University, Baoding, Hebei 071002, P. R. of China
,
Zhong-Quan Liu∗
b   State Key Laboratory Cultivation Base for TCM Quality and Efficacy, College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, Jiangsu, 210023, P. R. of China
,
Zejiang Li  ∗
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry & Environmental Science Hebei University, Baoding, Hebei 071002, P. R. of China
› Author AffiliationsThis project is supported by the National Natural Science Foundation of China (21702044, 21971116), the Natural Science Foundation of Hebei Province (B2020201014, B2022201059), the Science and Technology Project of Hebei Education Department (QN2019063), and the Research Innovation Team of College of Chemistry and Environmental Science of Hebei University (hxkytd-py2102).
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Abstract

Photoinduced tandem cyclization of alkynes with phenylsulfinic acids has been accomplished, which gives a mild strategy for the preparation of sulfone-substituted seven-membered N-heterocycles. A variety of scaled-up experiments, further transformations, and mechanistic studies were also operated in the follow-up work.

Key words

photoinduced - tandem cyclization - alkynes - sulfone - seven-membered N-heterocycles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1914-1722.
  • Supporting Information


Publication History

Received: 03 July 2022

Accepted after revision: 01 August 2022

Accepted Manuscript online:
01 August 2022

Article published online:
24 August 2022

© 2022. Thieme. All rights reserved

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