Three-component coupling approach for the synthesis of diverse heterocycles utilizing reactive nitrilium trapping

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Abstract

The formation of an unexpected heterocyclic scaffold, a benzoxazole, in a three-component reaction between a ketone, isocyanide, and 2-aminophenol was encountered. This reaction involved a benzo[b][1,4]oxazine intermediate resulting from intramolecular attack of the aminophenol hydroxyl group on the nitrilium ion. Unlike previous literature examples, the trapped nitrilium benzo[b][1,4]oxazine could readily be subjected to ring opening with bis-nucleophiles. The reaction scope includes simple linear as well as complex cyclic ketones and substituted 2-aminophenols. A representative benzoxazole product could be further diversified to yield drug-like compounds. © 2014 American Chemical Society.

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Váradi, A., Palmer, T. C., Notis, P. R., Redel-Traub, G. N., Afonin, D., Subrath, J. J., … Majumdar, S. (2014). Three-component coupling approach for the synthesis of diverse heterocycles utilizing reactive nitrilium trapping. Organic Letters, 16(6), 1668–1671. https://doi.org/10.1021/ol500328t

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