Benzophenanthridines. V. Investigation of the Rodionov-Suvorov scheme. Synthesis of 3,3-diethoxycarbonyl-2-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1-tetralone
Journal Article
·
· J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:5887282
Triethyl 1,3-bis(3,4-dimethoxyphenyl)propane-1,2,2-tricarboxylate was synthesized by the alkylation of the lithium enolate of ethyl homoveratrate with /alpha/-bromo(3,4-dimethoxybenzyl)malonic ester. It was converted by intramolecular acylation, catalyzed by BF/sub 3/ /times/ OEt/sub 2/, into the ACD synthon for the total synthesis of benzo(c)-phenanthridine alkaloids by the Rodionov-Suvorov scheme, i.e., 3,3-diethoxy-carbonyl-2-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1-tetralone. The structure of the synthesized substances agrees well with the data from elemental analysis and IR, /sup 1/H NMR, and mass spectra.
- Research Organization:
- D.I. Mendeleev Moscow Chemical Technology Institute (USSR)
- OSTI ID:
- 5887282
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 23:9; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACETIC ACID
ACYLATION
ALCOHOLS
ALKALOIDS
ALKOXIDES
ALKYLATION
BORON COMPOUNDS
BORON FLUORIDES
CARBON TETRACHLORIDE
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
COMPLEXES
DICARBOXYLIC ACIDS
ESTERS
ETHANOL
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROXY COMPOUNDS
INFRARED SPECTRA
KINETICS
LITHIUM COMPLEXES
MALONIC ACID
MASS SPECTRA
MONOCARBOXYLIC ACIDS
NMR SPECTRA
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
REACTION KINETICS
SPECTRA
SYNTHESIS
YIELDS
400201* -- Chemical & Physicochemical Properties
ACETIC ACID
ACYLATION
ALCOHOLS
ALKALOIDS
ALKOXIDES
ALKYLATION
BORON COMPOUNDS
BORON FLUORIDES
CARBON TETRACHLORIDE
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
COMPLEXES
DICARBOXYLIC ACIDS
ESTERS
ETHANOL
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROXY COMPOUNDS
INFRARED SPECTRA
KINETICS
LITHIUM COMPLEXES
MALONIC ACID
MASS SPECTRA
MONOCARBOXYLIC ACIDS
NMR SPECTRA
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
REACTION KINETICS
SPECTRA
SYNTHESIS
YIELDS