General Synthesis of 2-Substituted Benzoxazoles Based on Tf2O-Promoted Electrophilic Activation of Tertiary Amides

We report a method for the synthesis of 2-substituted benzoxazoles from tertiary amides and 2-aminophenols in the presence of triflic anhydride (Tf2O) and 2-Fluoropyridine (2-F-Pyr). The cascade reaction involves the activation of the amide carbonyl group by Tf2O, nucleophilic addition, intramolecul...

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Published inMolecules (Basel, Switzerland) Vol. 30; no. 7; p. 1510
Main Authors Li, Hongchen, Wang, Xingyong, Zhao, Fujun, Wang, Lu, Fu, Songbao
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 28.03.2025
Subjects
benzoxazoles
electrophilic activation
Methods
Nitrogen
tertiary amides
triflic anhydride
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Summary:We report a method for the synthesis of 2-substituted benzoxazoles from tertiary amides and 2-aminophenols in the presence of triflic anhydride (Tf2O) and 2-Fluoropyridine (2-F-Pyr). The cascade reaction involves the activation of the amide carbonyl group by Tf2O, nucleophilic addition, intramolecular cyclization, and elimination. Furthermore, we explore the scope of this method by varying both the amide and 2-aminophenol substrates, highlighting its versatility in the synthesis of a wide range of functionalized benzoxazole derivatives.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules30071510