Amination of the pyridinium cations in betaines. Synthesis of substituted pyrimido(5,6-c)-1'-azaquinolizine and its dihydro analogs
The pyridinium cations within betaines can be aminated under mild conditions with aqueous ammonia, ultimately undergoing cyclization to a new tricyclic system: 4-substituted-3,5-dioxopyrimido(5,6-c)-1'-azaquinolizine. Intermediates in the reaction are 4-substituted-3,5-dioxo-2,2-dihydropyrimido(5,6-c)-6H-1'-quinolizines. Formation of the methylene group is coupled with transfer of an atom of hydrogen or deuterium from the ..cap alpha..-carbon of the dihydropyridine in compound II to the carbon atom of the azomethine group. The NMR spectrum is represented by the methylene proton signal (3.96 ppm) and by the multiplets of the pyridine and phenyl protons centered at 7.63 and 6.38 ppm respectively. Upon chloranil oxidation, and upfield shift of the pyridine protons is observed: the ..cap alpha..-proton forms a doublet (10.05 ppm, J= 6 Hz), the ..beta..-protons form a doublet and a triplet with centers at 8.57 (J = 8 Hz) and 8.22 (J = 7 Hz) ppm respectively, and the ..gamma..-proton forms a triplet at 8.8 (J = 7 Hz) ppm.
- Research Organization:
- Institute of Physical Organic Chemistry and Coal Chemistry, Donetsk (USSR)
- OSTI ID:
- 7005042
- 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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Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
AMINATION
AMINES
AMINO ACIDS
AMMONIA
AMMONIUM COMPOUNDS
AROMATICS
AZAARENES
AZINES
BETAINE
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
COUPLING CONSTANTS
DEHYDROCYCLIZATION
DEUTERIUM
DRUGS
HETEROCYCLIC COMPOUNDS
HYDRIDES
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPES
ISOTOPIC EXCHANGE
J-J COUPLING
LIGHT NUCLEI
LIPOTROPIC FACTORS
MULTIPLETS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NMR SPECTRA
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRIDINES
PYRIDINIUM COMPOUNDS
PYRIMIDINES
QUATERNARY COMPOUNDS
QUINOLINES
REACTION INTERMEDIATES
SPECTRA
STABLE ISOTOPES
SYNTHESIS