METHOD OF PREPARING 1-HYDROXY-PYRID-2-ONES

FIELD: organic chemistry. SUBSTANCE: described is method of preparing compounds of formula I: which are well known for their bacterial and antifungal activities wherein R1 is branched or unbranched alkyl having 1 to 17 carbon atoms, branched or unbranched alkyl having 2 to 17 carbon toms, cycloalkyl...

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Hauptverfasser: ANUSHIRVAN PEJMAN, ADOL'F KHAJNTS LINKIS, DITER BERND ROJSHLING
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creator ANUSHIRVAN PEJMAN
ADOL'F KHAJNTS LINKIS
DITER BERND ROJSHLING
description FIELD: organic chemistry. SUBSTANCE: described is method of preparing compounds of formula I: which are well known for their bacterial and antifungal activities wherein R1 is branched or unbranched alkyl having 1 to 17 carbon atoms, branched or unbranched alkyl having 2 to 17 carbon toms, cycloalkyl having 3-8 carbon atoms in the ring, said cycloalkyl residue being not substituted or substituted by means of 1-3 alkyl residues each, depending on circumstances, with 1-3 carbon atoms, phenyl, phenyloxy (C1-C4) alkyl or phenyl-(C1-C4) alkyl, phenyl, phenyloxy-(C1-C4) alkyl and phenyl-(C1-C4) alkyl residues being not substituted or substituted in the aromatic ring with by means of 1-3 (C1-C6) alkyl, benzyl, (C1-C6) alkoxy, phenoxy or halide residues, said cycloalkyl, phenyl, phenyloxy (C1-C4) alkyl residues being connected directly or through methylene or ethylene group with pirydone ring; and R2 is hydrogen atom, alkyl having 1-6 carbon atoms, alkenyl having 2-6 carbon atoms or benzyl residue by reacting pyrone of formula II: , residues R1 and R2 are as defined in formula I for corresponding residues R1 and R2, with hydroxyammonium salt in solvent and in the presence of alkali metal carbonate and/or alkali metal hydrocarbonate in amount of 0.8-5 equivalents calculated for hydroxyammonium salt, and reaction is carried out in the presence or organic acid or salt thereof. Method makes it possible to make process more profitable. EFFECT: more efficient preparation method. 10 cl, 30 ex, 3 tbl
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SUBSTANCE: described is method of preparing compounds of formula I: which are well known for their bacterial and antifungal activities wherein R1 is branched or unbranched alkyl having 1 to 17 carbon atoms, branched or unbranched alkyl having 2 to 17 carbon toms, cycloalkyl having 3-8 carbon atoms in the ring, said cycloalkyl residue being not substituted or substituted by means of 1-3 alkyl residues each, depending on circumstances, with 1-3 carbon atoms, phenyl, phenyloxy (C1-C4) alkyl or phenyl-(C1-C4) alkyl, phenyl, phenyloxy-(C1-C4) alkyl and phenyl-(C1-C4) alkyl residues being not substituted or substituted in the aromatic ring with by means of 1-3 (C1-C6) alkyl, benzyl, (C1-C6) alkoxy, phenoxy or halide residues, said cycloalkyl, phenyl, phenyloxy (C1-C4) alkyl residues being connected directly or through methylene or ethylene group with pirydone ring; and R2 is hydrogen atom, alkyl having 1-6 carbon atoms, alkenyl having 2-6 carbon atoms or benzyl residue by reacting pyrone of formula II: , residues R1 and R2 are as defined in formula I for corresponding residues R1 and R2, with hydroxyammonium salt in solvent and in the presence of alkali metal carbonate and/or alkali metal hydrocarbonate in amount of 0.8-5 equivalents calculated for hydroxyammonium salt, and reaction is carried out in the presence or organic acid or salt thereof. 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SUBSTANCE: described is method of preparing compounds of formula I: which are well known for their bacterial and antifungal activities wherein R1 is branched or unbranched alkyl having 1 to 17 carbon atoms, branched or unbranched alkyl having 2 to 17 carbon toms, cycloalkyl having 3-8 carbon atoms in the ring, said cycloalkyl residue being not substituted or substituted by means of 1-3 alkyl residues each, depending on circumstances, with 1-3 carbon atoms, phenyl, phenyloxy (C1-C4) alkyl or phenyl-(C1-C4) alkyl, phenyl, phenyloxy-(C1-C4) alkyl and phenyl-(C1-C4) alkyl residues being not substituted or substituted in the aromatic ring with by means of 1-3 (C1-C6) alkyl, benzyl, (C1-C6) alkoxy, phenoxy or halide residues, said cycloalkyl, phenyl, phenyloxy (C1-C4) alkyl residues being connected directly or through methylene or ethylene group with pirydone ring; and R2 is hydrogen atom, alkyl having 1-6 carbon atoms, alkenyl having 2-6 carbon atoms or benzyl residue by reacting pyrone of formula II: , residues R1 and R2 are as defined in formula I for corresponding residues R1 and R2, with hydroxyammonium salt in solvent and in the presence of alkali metal carbonate and/or alkali metal hydrocarbonate in amount of 0.8-5 equivalents calculated for hydroxyammonium salt, and reaction is carried out in the presence or organic acid or salt thereof. 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subjects APPARATUS THEREFOR
CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
PERFORMING OPERATIONS
PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
THEIR RELEVANT APPARATUS
TRANSPORTING
title METHOD OF PREPARING 1-HYDROXY-PYRID-2-ONES
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