10.1021/acs.joc.7b00811.s001
Kento Iwai
Kento
Iwai
Haruyasu Asahara
Haruyasu
Asahara
Nagatoshi Nishiwaki
Nagatoshi
Nishiwaki
Synthesis of Functionalized
3‑Cyanoisoxazoles
Using a Dianionic Reagent
American Chemical Society
2017
series
nitronate ion
cycloaddition
dianionic cyano
Michael addition
azide
reactive
3- cyano group
dipolar
5- acylated 3- cyanoisoxazoles
5- acyl
Synthesi
nitroacetate
dianionic reagent
pyridine ring
equivalent
Dianionic Reagent
ethanolysi
nitroacetonitrile
4- aryl group
tetrazole
Functionalized
aci
isoxazolo
intramolecular nucleophilic substitution
quinoline
ketone
formation
Cyanoisoxazole
ethyl ester
α-
chloro
2017-05-04 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Functionalized_3_Cyanoisoxazoles_Using_a_Dianionic_Reagent/4986659
A series of 5-acylated 3-cyanoisoxazoles
were efficiently synthesized
by the Michael addition of dianionic cyano-<i>aci</i>-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-<i>c</i>]quinoline
derivative.