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Continuous-Flow Direct Azidation of Alcohols and Peroxides for the Synthesis of Quinoxalinone, Benzooxazinone, and Triazole Derivatives

Akanksha M. Pandey, Shankhajit Mondal and Boopathy Gnanaprakasam*

*Department of Chemistry, Indian Institute of Science Education and Research, Pune 411008, India, Email:

A. M. Pandey, S. Mondal, B. Gnanaprakasam, J. Org. Chem., 2022, 87, 9926-9939.

DOI: 10.1021/acs.joc.2c00941

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A continuous-flow direct azidation of various alcohols with TMSN3 is mediated by Amberlyst-15 as a recyclable catalyst. While reactions of 3-hydroxy-2-oxindoles provide azide-functionalized quaternary stereocenters, peroxyoxindole generate 2-azido-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives. Continuous-flow Cu-catalyzed click reactions and reductions with PPh3 are also reported.

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Key Words

benzyl azides, flow chemistry

ID: J42-Y2022