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Condensed pyridines. 6. Synthesis and structure of adamantyl-, cyclopropyl- and alkyl-substituted 3-halomethyl-2,3-dihydro-8-cyanothiazolo(3,2-a)pyridinium salts and their oxazolo and selenazolo derivatives

Journal Article · · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)
DOI:https://doi.org/10.1007/BF00476391· OSTI ID:6961717
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The reaction of substituted 2-cyanopyridin-2(1H)-ones and their thione and selenone derivatives with allyl bromide gives the corresponding 2-allyloxy-, 2-allylmercapto-, and 2-allylseleno-3-pyridines, which upon treatment with halogens, form intramolecular quaternization products, namely, 3-halomethyl-2,3-dihydro-8-cyanooxazole(3,2-a)pyridinium salts and their thiazolo and selen-azolo analogs. X-ray diffraction structural analysis was used to determine the structure of 3-bromomethyl-2,3-dihydro-5,7-dimethyl-8-cyanothiazolo(3,2-a)pyridinium perchlorate. The IR spectra were taken in KBr pellets on a UR-20 spectrometer. The UV spectra were taken on a Specord UV-vis spectrometer in ethanol and DMF. The PMR spectra were taken on a Bruker WM-250 spectrometer at 250 MHz in CDCl/sub 3/ and DMSO-d/sub 6/ with TMS as the internal standard.
Research Organization:
N. D. Zelinskii Institute of Organic Chemistry, Moscow (USSR)
OSTI ID:
6961717
Journal Information:
Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 23:5; ISSN CHCCA
Country of Publication:
United States
Language:
English

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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
AMINES
AMMONIUM COMPOUNDS
ANGULAR MOMENTUM
AZINES
AZOLES
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
CHLOROFORM
COHERENT SCATTERING
COUPLING
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DIFFRACTION
DMSO
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOTOPE EFFECTS
J-J COUPLING
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXAZOLES
OXYGEN COMPOUNDS
PARTICLE PROPERTIES
PERCHLORATES
PYRIDINES
PYRIDINIUM COMPOUNDS
QUATERNARY COMPOUNDS
SCATTERING
SELENIUM COMPOUNDS
SPECTRA
SPIN
STRUCTURAL CHEMICAL ANALYSIS
SULFOXIDES
SYNTHESIS
THIAZOLES
ULTRAVIOLET SPECTRA
X-RAY DIFFRACTION