Reactivity and stereochemical structure of 4-hydroxy- and 4-alkoxyhexahydropyrimidine-2-thiones
Substituted 4-hydroxyhexahydropyrimidine-2-thiones were obtained by the reaction of ..beta..-isothiocyanatoaldehydes with ammonia or methylamine. When heated with alcohols in the presence of p-toluenesulfonic acids, the synthesized compounds gave the corresponding 4-alkoxyhexahydropyrimidine-2-thiones, which were converted into other 4-alkoxy derivatives by the action of the respective alcohols and were hydrolyzed to the initial 4-hydroxyhexahydropyrimidine-2-thiones by the action of an aqueous solution of oxalic acid or potassium hydroxide. The reaction of the 4-hydroxyhexahydropyrimidine-2-thiones with methyl iodide led to the formation of 2-methylthio-4-hydroxy-3,4,5,6-tetrahydropyrimidine hydriodides. It was shown by PMR spectroscopy that the stereoisomers in which the hydroxyl (or alkoxyl) group has the axial orientation are thermodynamically more stable.
- Research Organization:
- M.V. Lomonosov Moscow Institute of Fine Chemical Technology, USSR
- OSTI ID:
- 6290178
- Journal Information:
- Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 21:2; ISSN CHCCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
AZINES
CARBOXYLIC ACIDS
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
COUPLING
COUPLING CONSTANTS
DEUTERIUM COMPOUNDS
DICARBOXYLIC ACIDS
ELECTRONIC STRUCTURE
ENERGY LEVELS
ESTERS
EXCITED STATES
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATION
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROXIDES
INFRARED SPECTRA
INTERMEDIATE COUPLING
IODINATED ALIPHATIC HYDROCARBONS
IODINATION
ISOMERIZATION
ISOMERS
J-J COUPLING
METHYL IODIDE
MOLECULAR STRUCTURE
NMR SPECTRA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SOLVENTS
ORGANIC SULFUR COMPOUNDS
OXALIC ACID
OXYGEN COMPOUNDS
POLYCYCLIC SULFUR HETEROCYCLES
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
PYRIMIDINES
SOLVENTS
SPECTRA
SPECTRAL SHIFT
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SULFONIC ACID ESTERS
SYNTHESIS
ULTRAVIOLET SPECTRA
VIBRATIONAL STATES
YIELDS