%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