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

David Amantini, Francesco Fringuelli,* Oriana Piermatti, Ferdinando Pizzo, Ennio Zunino and Luigi Vaccaro*

*CEMIN, Centro di Eccellenza Materiali Innovativi Nanostrutturati, Dipartimento di Chimica, Università di Perugia, Via Elce di Sotto 8, I-06123 Perugia, Email: frifraunipg.it, luigiunipg.it

D. Amantini, F. Fringuelli, O. Piermatti, F. Pizzo, E. Zunino, L. Vaccaro, J. Org. Chem., 2005, 70, 6526-6529.

DOI: 10.1021/jo0507845

Abstract

TBAF-catalyzed [3 + 2] cycloadditions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes with TMSN₃ under solvent-free conditions (SFC) allow the preparation of 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles under mild reaction conditions with good to excellent yields.

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Key Words

1,2,3-Triazoles, 1,3-dipolar cycloaddition

ID: J42-Y2005-1090

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

David Amantini, Francesco Fringuelli,* Oriana Piermatti, Ferdinando Pizzo, Ennio Zunino and Luigi Vaccaro*

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