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TEMPO-Mediated Aza-Diels–Alder Reaction: Synthesis of Tetrahydropyridazines Using Ketohydrazones and Olefins

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journal contribution
posted on 27.04.2016, 19:18 by Xiu-Long Yang, Xie-Xue Peng, Fei Chen, Bing Han
A novel, facile, and efficient method for the synthesis of tetrahydropyridazines by a one-pot tandem reaction of easily accessible ketohydrazones and olefins in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) has been successfully developed. The reaction involves the initial generation of azoalkenes from direct oxidative dehydrogenation of ketohydrazones using TEMPO as the commercially available oxidant, followed by a subsequent aza-Diels–Alder reaction with olefins.