Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3 + 2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions.
TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.
Amantini
David
D
CEMIN, Centro di Eccellenza Materiali Innovativi Nanostrutturati, Dipartimento di Chimica, Università di Perugia, Via Elce di Sotto 8, I-06123 Perugia, Italy.
Fringuelli
Francesco
F
Piermatti
Oriana
O
Pizzo
Ferdinando
F
Zunino
Ennio
E
Vaccaro
Luigi
L
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D012997:Solvents; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
D000890:Anti-Infective Agents; D009574:Nitro Compounds; D012997:Solvents; D014230:Triazoles