Synthesis of 2‐Aryl‐2H‐1,2,3‐triazoles via P(OMe)3‐Promoted Intramolecular Transannulation of 4‐Diazenylisoxazol‐5(4H)‐ones DOI
Pavel А. Sakharov, Alexander N. Koronatov, Alexander F. Khlebnikov

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 15, 2024

Abstract Trimethyl phosphite promotes the synthesis of 2,4,5‐trisubstituted 2 H ‐1,2,3‐triazoles. The protocol developed affords a two‐step method towards triazoles from available reagents. 3,4‐Disubstituted isoxazolones are initially coupled with diazonium tetrafluoroborates. subsequent reaction is triggered by single electron transfer to diazenylisoxazolone under heating or blue LED irradiation at room temperature. radical anion cascade proceeds via ring opening/decarboxylation/cyclization sequence. synthesized show promising fluorescence in region 340 nm 450 quantum yield up 81.6%. emission energy depends slightly on substituent nature triazole carbon atoms. If an electron‐donor group introduced into N2 ring, it results bathochromic shift luminescence energy.

Language: Английский

Synthesis of 2‐Aryl‐2H‐1,2,3‐triazoles via P(OMe)3‐Promoted Intramolecular Transannulation of 4‐Diazenylisoxazol‐5(4H)‐ones DOI
Pavel А. Sakharov, Alexander N. Koronatov, Alexander F. Khlebnikov

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 15, 2024

Abstract Trimethyl phosphite promotes the synthesis of 2,4,5‐trisubstituted 2 H ‐1,2,3‐triazoles. The protocol developed affords a two‐step method towards triazoles from available reagents. 3,4‐Disubstituted isoxazolones are initially coupled with diazonium tetrafluoroborates. subsequent reaction is triggered by single electron transfer to diazenylisoxazolone under heating or blue LED irradiation at room temperature. radical anion cascade proceeds via ring opening/decarboxylation/cyclization sequence. synthesized show promising fluorescence in region 340 nm 450 quantum yield up 81.6%. emission energy depends slightly on substituent nature triazole carbon atoms. If an electron‐donor group introduced into N2 ring, it results bathochromic shift luminescence energy.

Language: Английский

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