%0 Generic
%A Iwai, Kento
%A Asahara, Haruyasu
%A Nishiwaki, Nagatoshi
%D 2017
%T Synthesis of Functionalized
3‑Cyanoisoxazoles
Using a Dianionic Reagent
%U https://acs.figshare.com/articles/dataset/Synthesis_of_Functionalized_3_Cyanoisoxazoles_Using_a_Dianionic_Reagent/4986656
%R 10.1021/acs.joc.7b00811.s002
%2 https://ndownloader.figshare.com/files/8394725
%K series
%K nitronate ion
%K cycloaddition
%K dianionic cyano
%K Michael addition
%K azide
%K reactive
%K 3- cyano group
%K dipolar
%K 5- acylated 3- cyanoisoxazoles
%K 5- acyl
%K Synthesi
%K nitroacetate
%K dianionic reagent
%K pyridine ring
%K equivalent
%K Dianionic Reagent
%K ethanolysi
%K nitroacetonitrile
%K 4- aryl group
%K tetrazole
%K Functionalized
%K aci
%K isoxazolo
%K intramolecular nucleophilic substitution
%K quinoline
%K ketone
%K formation
%K Cyanoisoxazole
%K ethyl ester
%K α-
%K chloro
%X A series of 5-acylated 3-cyanoisoxazoles
were efficiently synthesized
by the Michael addition of dianionic cyano-aci-nitroacetate
to α-chloro-α,β-unsaturated ketones followed by
intramolecular nucleophilic substitution of the nitronate ion intermediate.
In this process, the dianionic reagent serves as the safe synthetic
equivalent of the explosive nitroacetonitrile. The 3-cyano group is
sufficiently reactive toward ethanolysis and 1,3-dipolar cycloaddition
with an azide to afford ethyl ester and tetrazole, respectively. A
pyridine ring between the 5-acyl and the 4-aryl group was also constructed.
This led to the formation of the isoxazolo[5,4-c]quinoline
derivative.
%I ACS Publications