Application of Pyridinium 1,4-Zwitterionic Thiolates: Synthesis of Benzopyridothiazepines and Benzothiophenes

Pyridinium 1,4-zwitterionic thiolates, as a novel kind of sulfur-containing synthon, have been applied to the synthesis of 12aH-benzo­[f]­pyrido­[1,2-d]­[1,4]­thiazepines and benzo­[b]­thiophenes. Benzopyrido­thiazepines were produced through a 1,5-dipolar cycloaddition reaction from pyridinium 1,4-...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-05, Vol.85 (10), p.6794-6802
Main Authors: Cheng, Bin, Li, Yuntong, Wang, Taimin, Zhang, Xinping, Li, Hui, He, Yixuan, Li, Yun, Zhai, Hongbin
Format: Article
Language:English
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Summary:Pyridinium 1,4-zwitterionic thiolates, as a novel kind of sulfur-containing synthon, have been applied to the synthesis of 12aH-benzo­[f]­pyrido­[1,2-d]­[1,4]­thiazepines and benzo­[b]­thiophenes. Benzopyrido­thiazepines were produced through a 1,5-dipolar cycloaddition reaction from pyridinium 1,4-zwitterionic thiolates with arynes, whereas benzothiophenes as side products were generated via a [3 + 2] cascade cyclization reaction. The [5 + 2] reaction mode of pyridinium 1,4-zwitterionic thiolates is disclosed for the first time.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00374