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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Visible-Light-Induced Radical Cascade Sulfonylation/Cyclization to Access Sulfonylated Benzazepines and Benzoxepines
Xiaowei Zhao1, Wanqing Zhao1, Anxu Pan1
1Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.
Abstract:
A visible light-mediated sulfonylation of 1-(2-(allyloxy)aryl)-3,3-bis(methylthio)prop-2-en-1-ones and N-allyl-N-(2-(3,3-bis(methylthio) acryloyl)aryl)-4-methylbenzenesulfonamides for the synthesis of a wide range of sulfonylated benzazepines and benzoxepines is developed. This protocol features simple operation, photocatalyst- and additive-free, good regioselectivity, and the use of K2S2O5 as a sulfur dioxide substitute, providing a novel environmentally friendly strategy to access the seven-membered heterocycles. The mechanistic studies revealed that aryldiazonium tetrafluoroborates served as electron acceptors, enabling the formation of EDA complexes with α-oxoketene dithioacetal substrates.
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