Synthesis of 4-trifluoromethyl pyridazines via annulation of pyridinium ylides with trifluoroacetyl diazoester

Abstract

A base promoted annulation of pyridinium ylides with trifluoroacetyl diazoester has been reported. Highly functionalized 4-trifluoromethyl pyridazines were synthesized in good yields without the use of any heavy metal catalysts. The developed methodology was compatible with a variety of important functional groups. Mechanistic studies revealed that trifluoroacetylated hydrazone was an active intermediate of this three-component annulation. Synthetic versatility of the method via aminolysis and condensation toward amide- and pyridazino[4,5-c]pyridazine-derivatives has been showcased.