Synthesis of Pyrazolo[5,1-alpha]isoindoles and Pyrazolo[5,1-alpha]isoindole-3-carboxamides through One-Pot Cascade Reactions of 1-(2-Bromophenyl)buta-2,3-dien-1-ones with Isocyanide and Hydrazine or Acetohydrazide

摘要

A novel and efficient method for the construction of the pyrazolo[5,1-alpha]isoindole scaffold via a one-pot three-component cascade reaction of 1-(2-bromophenyl)buta-2,3-dien-1-one with hydrazine and isocyanide promoted by a Pd catalyst is described. This cascade process proceeds through initial condensation of the allenic ketone with hydrazine followed by Pd-catalyzed isocyanide insertion into the C-Br bond and intramolecular C-N bond formation. Interestingly, when acetohydrazide was used in place of hydrazine, a more sophisticated procedure involving condensation, isocyanide insertion into C-H and C-Br bonds, deacetylation, and formation of C-C, C-O, and C-N bonds occurred to afford pyrazolo[5,1-a]isoindole-3-carboxamides with good efficiency.