Preparation of derivatives of 1,2-dihydro- and 1,2,3,6-tetrahydro-pyrazinones from acylated 1,2-hydroxylamino ketones

Journal Article · Wed Oct 01 00:00:00 EDT 1986 · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF00542782· OSTI ID:6335443

Reznikova, T I; Tikhonov, A Ya; Volodarskii, L B

N-(2-Oxoalkyl)-2-chloroacetohydroxamic acids were obtained by acylation of 1,2-hydroxylamino ketones with chloroacetyl chloride. Their reaction with urotropin and sodium azide gives urotropinium salts and acetoxyhydroxamic acid azides. 1-Hydroxy-2-oxo-1,2,3,6-tetrahydropyrazines were obtained by treating N-(2-oxoalkyl)-2-chloroacetohydroxyamic acids with ammonia, and also by reacting the urotropinium salts and azides of acetohydroxamic acids with hydrochloric acid and triphenylphosphine, respectively. The reaction of N-(1-methyl-2-oxo-2-phenyl-ethyl)-2-chloroacetohydroxamic acid with urotropin in an acid medium leads to the formation of 6-methyl-2-oxo-5-phenyl-1,2-dihydropyrazine.

• Research Organization: Novosibirsk Institute of Organic Chemistry, USSR
• OSTI ID: 6335443
• Journal Information: Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Vol. 22:4; Other Information: Translated from Khim. Geterotsikl. Soedin.; 22: No.4, 509-513(Apr 1986)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
HYDROXY COMPOUNDS
ACYLATION
DEHYDROCYCLIZATION
KETONES
PYRAZINES
NMR SPECTRA
SYNTHESIS
ACETONITRILE
ACTIVATION ENERGY
AMMONIA
AZIDES
CHEMICAL REACTION YIELD
CHLOROFORM
COUPLING CONSTANTS
DEUTERATION
DEUTERIUM COMPOUNDS
HYDROXAMIC ACIDS
HYPERFINE STRUCTURE
INFRARED SPECTRA
J-J COUPLING
METHANOL
ORGANIC CHLORINE COMPOUNDS
ORGANIC SOLVENTS
ULTRAVIOLET SPECTRA
UROTROPIN
VIBRATIONAL STATES
ALCOHOLS
AMINES
AZINES
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
COUPLING
ENERGY
ENERGY LEVELS
EXCITED STATES
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDRIDES
HYDROGEN COMPOUNDS
INTERMEDIATE COUPLING
NITRILES
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SOLVENTS
SPECTRA
YIELDS
400201* - Chemical & Physicochemical Properties
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Molecular & Chemical Physics- Atomic & Molecular Properties & Theory