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), Vol. 23:5; Other Information: Translated from Khim. Geterotsikl. Soedin.; 23: No. 5, 677-680(May 1987)
- Country of Publication:
- United States
- Language:
- English
Similar Records
2-Methyl-5,6-dihydro-2H-pyran in the Simmons-Smith reaction
Reactions of (chloroethynyl)phosphonates with neutral nucleophiles
Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
PYRIDINIUM COMPOUNDS
AMINATION
DEHYDROCYCLIZATION
PYRIMIDINES
NMR SPECTRA
SYNTHESIS
QUINOLINES
AMMONIA
BETAINE
CHEMICAL SHIFT
COUPLING CONSTANTS
DEUTERIUM
HYDROGEN TRANSFER
ISOMERIZATION
ISOTOPIC EXCHANGE
J-J COUPLING
MULTIPLETS
REACTION INTERMEDIATES
AMINES
AMINO ACIDS
AMMONIUM COMPOUNDS
AROMATICS
AZAARENES
AZINES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
COUPLING
DRUGS
HETEROCYCLIC COMPOUNDS
HYDRIDES
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INTERMEDIATE COUPLING
ISOTOPES
LIGHT NUCLEI
LIPOTROPIC FACTORS
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PYRIDINES
QUATERNARY COMPOUNDS
SPECTRA
STABLE ISOTOPES
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory