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 in | Molecules (Basel, Switzerland) Vol. 30; no. 7; p. 1510 |
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| Language | English |
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| 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. |
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| AbstractList | 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. 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.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. |
| Author | Li, Hongchen Wang, Xingyong Wang, Lu Fu, Songbao Zhao, Fujun |
| Author_xml | – sequence: 1 givenname: Hongchen orcidid: 0009-0007-8022-2023 surname: Li fullname: Li, Hongchen – sequence: 2 givenname: Xingyong surname: Wang fullname: Wang, Xingyong – sequence: 3 givenname: Fujun surname: Zhao fullname: Zhao, Fujun – sequence: 4 givenname: Lu orcidid: 0000-0002-7988-2741 surname: Wang fullname: Wang, Lu – sequence: 5 givenname: Songbao surname: Fu fullname: Fu, Songbao |
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| Snippet | 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... |
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| SubjectTerms | benzoxazoles electrophilic activation Methods Nitrogen tertiary amides triflic anhydride |
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| Title | General Synthesis of 2-Substituted Benzoxazoles Based on Tf2O-Promoted Electrophilic Activation of Tertiary Amides |
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