Synthesis of Various 2‑Aminobenzoxazoles: The Study of Cyclization and Smiles Rearrangement

This study reports two synthetic approaches leading to 2-aminobenzoxazoles and their N-substituted analogues. Our first synthetic strategy involves a reaction between various o-aminophenols and N-cyano-N-phenyl-p-toluenesulfonamide as a nonhazardous electrophilic cyanating agent in the presence of L...

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Bibliographic Details
Published in:ACS omega 2019-11, Vol.4 (21), p.19314-19323
Main Authors: Šlachtová, Veronika, Chasák, Jan, Brulíková, Lucie
Format: Article
Language:English
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Summary:This study reports two synthetic approaches leading to 2-aminobenzoxazoles and their N-substituted analogues. Our first synthetic strategy involves a reaction between various o-aminophenols and N-cyano-N-phenyl-p-toluenesulfonamide as a nonhazardous electrophilic cyanating agent in the presence of Lewis acid. The second synthetic approach uses the Smiles rearrangement upon activation of benzoxazole-2-thiol with chloroacetyl chloride. Both developed synthetic protocols are widely applicable, afford the desired aminobenzoxazoles in good to excellent yields, and use nontoxic and inexpensive starting material.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.9b02702