General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-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 (Tf<sub>2</sub>O) and 2-Fluoropyridine (2-F-Pyr). The cascade reaction involves the activation of the amide carbonyl group by Tf<sub>2<...
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MDPI AG
2025-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/7/1510 |
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| author | Hongchen Li Xingyong Wang Fujun Zhao Lu Wang Songbao Fu |
| author_facet | Hongchen Li Xingyong Wang Fujun Zhao Lu Wang Songbao Fu |
| author_sort | Hongchen Li |
| collection | DOAJ |
| description | We report a method for the synthesis of 2-substituted benzoxazoles from tertiary amides and 2-aminophenols in the presence of triflic anhydride (Tf<sub>2</sub>O) and 2-Fluoropyridine (2-F-Pyr). The cascade reaction involves the activation of the amide carbonyl group by Tf<sub>2</sub>O, 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. |
| format | Article |
| id | doaj-art-ca343f8b31b044b2b5834a61b90a0baf |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-ca343f8b31b044b2b5834a61b90a0baf2025-08-20T03:03:28ZengMDPI AGMolecules1420-30492025-03-01307151010.3390/molecules30071510General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of Tertiary AmidesHongchen Li0Xingyong Wang1Fujun Zhao2Lu Wang3Songbao Fu4CNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, ChinaCNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, ChinaCNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, ChinaCNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, ChinaCNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, ChinaWe report a method for the synthesis of 2-substituted benzoxazoles from tertiary amides and 2-aminophenols in the presence of triflic anhydride (Tf<sub>2</sub>O) and 2-Fluoropyridine (2-F-Pyr). The cascade reaction involves the activation of the amide carbonyl group by Tf<sub>2</sub>O, 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.https://www.mdpi.com/1420-3049/30/7/1510benzoxazoleselectrophilic activationtriflic anhydridetertiary amides |
| spellingShingle | Hongchen Li Xingyong Wang Fujun Zhao Lu Wang Songbao Fu General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of Tertiary Amides Molecules benzoxazoles electrophilic activation triflic anhydride tertiary amides |
| title | General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of Tertiary Amides |
| title_full | General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of Tertiary Amides |
| title_fullStr | General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of Tertiary Amides |
| title_full_unstemmed | General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of Tertiary Amides |
| title_short | General Synthesis of 2-Substituted Benzoxazoles Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of Tertiary Amides |
| title_sort | general synthesis of 2 substituted benzoxazoles based on tf sub 2 sub o promoted electrophilic activation of tertiary amides |
| topic | benzoxazoles electrophilic activation triflic anhydride tertiary amides |
| url | https://www.mdpi.com/1420-3049/30/7/1510 |
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