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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

Supporting Info

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

CEMIN, Centro di Eccellenza Materiali Innovativi Nanostrutturati, Dipartimento di Chimica, Universit di Perugia, Via Elce di Sotto 8, I-06123 Perugia, Italy frifra@unipg.it; luigi@unipg.it

J. Org. Chem., 2005, 70 (16), pp 6526–6529

DOI: 10.1021/jo0507845

Publication Date (Web): July 9, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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.

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