jo7b00811_si_002.cif (21.65 kB)
Synthesis of Functionalized 3‑Cyanoisoxazoles Using a Dianionic Reagent
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posted on 2017-05-04, 00:00 authored by Kento Iwai, Haruyasu Asahara, Nagatoshi NishiwakiA 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.
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seriesnitronate ioncycloadditiondianionic cyanoMichael additionazidereactive3- cyano groupdipolar5- acylated 3- cyanoisoxazoles5- acylSynthesinitroacetatedianionic reagentpyridine ringequivalentDianionic Reagentethanolysinitroacetonitrile4- aryl grouptetrazoleFunctionalizedaciisoxazolointramolecular nucleophilic substitutionquinolineketoneformationCyanoisoxazoleethyl esterα-chloro
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