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

Year: 2025

Type: article

Abstract: 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.

Source: Molecules

DOI: 10.3390/molecules30071510

Authors: Hongchen Li, Xingyong Wang, Fujun Zhao, Lu Wang, Songbao Fu

Institutions: China National Offshore Oil Corporation (China), Tsinghua University

Language: English

Topic: Synthesis and Reactions of Organic Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,258

OpenAlex ID: W4408993247

FWCI: 0.291

Cites: 51

Cited by: 1

Related to: 10