%0 Journal Article %A Tian, Miaomiao %A He, Yan %A Zhang, Xinying %A Fan, Xuesen %D 2015 %T Synthesis of Pyrazolo[5,1‑a]isoindoles and Pyrazolo[5,1‑a]isoindole-3-carboxamides through One-Pot Cascade Reactions of 1‑(2-Bromophenyl)buta-2,3-dien-1-ones with Isocyanide and Hydrazine or Acetohydrazide %U https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Pyrazolo_5_1_i_a_i_isoindoles_and_Pyrazolo_5_1_i_a_i_isoindole_3_carboxamides_through_One_Pot_Cascade_Reactions_of_1_2_Bromophenyl_buta_2_3_dien_1_ones_with_Isocyanide_and_Hydrazine_or_Acetohydrazide/2142763 %R 10.1021/acs.joc.5b00997.s001 %2 https://acs.figshare.com/ndownloader/files/3776617 %K hydrazine %K condensation %K AcetohydrazideA novel %K Pyrazolo %K allenic ketone %K Pd catalyst %K formation %K pyrazolo %K isocyanide insertion %K cascade process proceeds %K bond %X A novel and efficient method for the construction of the pyrazolo­[5,1-a]­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. %I ACS Publications