Synthesis of 4-aryl-1 H-1, 2, 3-triazoles through TBAF-catalyzed [3+ 2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions

…, F Fringuelli, O Piermatti, F Pizzo…

Index: Fringuelli, Francesco; Pizzo, Ferdinando; Tortoioli, Simone; Vaccaro, Luigi Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8780 - 8785

Full Text: HTML

Citation Number: 106

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-1 H-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.