Synthesis of -dibromo 1,3-oxazines by NBS-mediated electrophilic cyclization of propargylic amides.

Org Biomol Chem

Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, China.

Published: June 2023

We present a highly efficient and practical method for synthesizing -dibromo 1,3-oxazines through 6- cyclization of propargylic amides, using -bromosuccinimide (NBS) as an electrophilic source. The metal-free reaction can be conducted under mild conditions with good functional group compatibility, delivering excellent yields of the desired products. Mechanistic studies suggest that the reaction proceeds a double electrophilic attack by NBS on the propargylic amide substrate.

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http://dx.doi.org/10.1039/d3ob00623aDOI Listing

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