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Synfacts 2011(3): 0327-0327
DOI: 10.1055/s-0030-1259446
DOI: 10.1055/s-0030-1259446
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Base-Catalyzed Synthesis of 1,2,4-Triazolines
D. Monge, K. L. Jensen, I. Marín, K. A. Jørgensen*
Aarhus University, Denmark
Further Information
Publication History
Publication Date:
16 February 2011 (online)
Significance
The authors report a base-catalyzed hydrazination-cyclization sequence for the one-pot synthesis of highly substituted 1,2,4-triazolines. The scope of the reaction proved to be very general regarding the azodicarboxylates and α-isocyano esters/amides. Even the base could be switched from nitrogen-containing structures to Ph3P, probably to a mechanism, which involves a Huisgen zwitterion intermediate. Furthermore, initial attempts towards an asymmetric version of the reaction are reported, using cinchonine-derived catalysts under phase-transfer conditions.