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Start Over Author "Kaixia Jian" Topic general chemistry
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1. Preparation of anthranils via chemoselective oxidative radical cyclization of 3-(2-azidoaryl) substituted propargyl alcohols

Author

Jian Xu, Chao Gao, Qingqing Xuan, Qiuling Song, Shuxian Zhu, and Kaixia Jian

Subjects
Radical, Iodobenzene, Metals and Alloys, chemistry.chemical_element, General Chemistry, Oxidative phosphorylation, Oxygen, Radical cyclization, Medicinal chemistry, Catalysis, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, chemistry, Transition metal, Propargyl, Materials Chemistry, Ceramics and Composites
Abstract

In the presence of K2S2O8 and HOAc, 3-(2-azidoaryl) substituted propargyl alcohols can go through chemoselective oxidative radical cyclizations to give a pool of anthranils based on Meyer-Schuster rearrangement. It's proposed that the cyclizations were triggered exclusively by the direct attack of oxygen radicals on the azides. The weak N-O bonds in anthranils could be easily cleaved in the presence of transition metal catalysts and went through aminations with 2-oxo-2-phenylacetic acid and iodobenzene.

Published
2021
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