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Synlett 2022; 33(17): 1733-1738
DOI: 10.1055/a-1914-1722
DOI: 10.1055/a-1914-1722
letter
Photoinduced Tandem Cyclization of Alkynes with Phenylsulfinic Acids: Access to Sulfone-Substituted Dioxodibenzothiazepines or Dibenzazepines
This 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).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1914-1722.
- Supporting Information
Publikationsverlauf
Eingereicht: 03. Juli 2022
Angenommen nach Revision: 01. August 2022
Accepted Manuscript online:
01. August 2022
Artikel online veröffentlicht:
24. August 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
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- 18 (E)-6-Isopropyl-2-methyl-11-[(phenylsulfonyl)methylene]-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-Dioxide – Typical ProcedureA mixture of N-(2-ethynylphenyl)-N-isopropylbenzenesulfonamide (1 equiv., 0.1 mmol), ArSO2H (3 equiv., 0.30 mmol), Ru(bpy)3Cl2·6H2O (0.01 equiv., 0.001 mmol), and CH3CN (3.5 mL) was added into a 10 mL quartz tube. The reaction system was operated with 18 W blue LEDs, rt. When it was finished, the mixture was condensed under vacuum and purified by column chromatography (petroleum ether/ethyl acetate = 5/1) to access a white solid, 23.13 mg, 51% yield.1H NMR (400 MHz, CDCl3): δ = 7.82 (t, J = 7.6 Hz, 3 H), 7.65 (t, J = 6.4 Hz, 1 H), 7.55 (t, J = 5.6 Hz, 2 H), 7.51 (d, J = 4.0 Hz, 3 H), 7.47–7.42 (m, 1 H), 7.31 (d, J = 8.0 Hz, 1 H), 7.19 (s, 1 H), 6.85 (s, 1 H), 4.26–4.19 (m, 1 H), 2.39 (s, 3 H), 1.41 (d, J = 6.4 Hz, 3 H), 1.32 (d, J = 8.0 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 151.8, 142.8, 140.8, 139.2, 137.5, 134.5, 133.9, 133.5, 133.4, 131.5, 131.4, 130.9, 130.3, 129.4, 129.3, 128.6, 127.8, 127.7, 55.2, 23.3, 22.6, 21.2. HRMS (ESI): m/z calcd for C24H24NO4S2 [M + H]+: 454.1147; found: 454.1145
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