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Heteryladamantanes. Communication 5. Synthesis of 6-(1-adamantyl)-3-cyanopyridin-2(1H)-selenone and related selenophenopyridines (in Russian)

Journal Article · · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)
DOI:https://doi.org/10.1007/BF00952929· OSTI ID:6476202
; ; ;
Reaction of the sodium salt of 3-(1-adamantyl)-1-hydroxyprop-1-en-3-one with cyanoselenoacetamide led to the first synthesis of 6-(1-adamantyl)-3-cyanopyridine-2-(1H)-selenone. 2-Seleno substituted 6-(1-adamantyl)-3-cyanopyridines have been obtained by alkylation of pyridineselenone with RCH/sub 2/HAl. Cyclization in the presence of base gives 2-substituted 6-(1-adamantyl)-3-aminoselenopheno(2,3-b)pyridines. Under electron impact conditions 2-mercapto and 2-seleno substituted 6-(1-adamantyl)-3-cyanopyridines undergo cyclization to the corresponding substituted thieno- and selenophenopyridines. The sulfur-containing compounds do not show an ion peak corresponding to separation of the adamantyl and pyridyl rings, whereas such a process does occur in the case of the selenium analogs.
Research Organization:
N.D. Zelenskii Institute of Organic Chemistry, Moscow, USSR
OSTI ID:
6476202
Journal Information:
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 35:2; ISSN BACCA
Country of Publication:
United States
Language:
Russian

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ADAMANTANE
ALKALI METAL COMPOUNDS
ALKANES
ANGULAR MOMENTUM
AZINES
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHROMATOGRAPHY
COLLISIONS
COMPLEXES
CYCLOALKANES
DEHYDROCYCLIZATION
ELECTRON COLLISIONS
ELECTRON-MOLECULE COLLISIONS
EVEN-EVEN NUCLEI
FERROCYANIDES
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE MASS NUCLEI
IRON COMPLEXES
ISOMERIC TRANSITION ISOTOPES
ISOTOPES
LIGHT NUCLEI
MASS SPECTRA
MOLECULE COLLISIONS
NMR SPECTRA
NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
PARTICLE PROPERTIES
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
PYRIDINES
RADIOISOTOPES
SELENIUM 80
SELENIUM COMPLEXES
SELENIUM ISOTOPES
SEPARATION PROCESSES
SODIUM COMPOUNDS
SPECTRA
SPIN
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SULFUR 32
SULFUR ISOTOPES
SYNTHESIS
THIN-LAYER CHROMATOGRAPHY
TRANSITION ELEMENT COMPLEXES
ULTRAVIOLET SPECTRA
YIELDS