Benzophenanthridines. IV. Synthesis of the benzo(c)phenanthridine ring from ethyl 6-(3,4-dimethoxyphenylacetyl)-3,4-dimethoxyphenylacetate. 11,12-Diacetoxy-6-methylfagaronine methyl ester perchlorate

Journal Article · Tue May 20 00:00:00 EDT 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6191365

Khokhlov, V A; Sladkov, V I; Kuleshova, L N; Suvorov, N N

The perchlorate of 11,12-diacetoxy-6-methylfaragonine methyl ester was synthesized from ethyl 6-(3,4-dimethoxyphenylacetyl)-3,4-dimethoxyphenylacetate through the formation of the corresponding 2-hydroxy-1,4- and then the 4-isopropyloxy-1,2-naphthaquinones, regioselective amination (leading to the formation of 4-methylamino-3-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2-naphthoquinone), and successive reductive acetylation and Bischler-Napiralski cyclization.

• Research Organization: D.I. Mendeleev Moscow Chemical Technology Institute, USSR
• OSTI ID: 6191365
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:12; ISSN JOCYA
• Country of Publication: United States
• Language: English

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
ABSORPTION SPECTRA
ACETYLATION
ACYLATION
ALKALOIDS
AMINATION
AROMATICS
BARYONS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACIDS
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINE COMPOUNDS
DEHYDROCYCLIZATION
ELEMENTARY PARTICLES
ESTERS
EVEN-ODD NUCLEI
FERMIONS
HADRONS
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROGEN 1
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
HYPERFINE STRUCTURE
INFRARED SPECTRA
IODINATED ALIPHATIC HYDROCARBONS
ISOTOPES
ISOTOPIC EXCHANGE
KETO ACIDS
LIGHT NUCLEI
NMR SPECTRA
NUCLEI
NUCLEONS
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXYGEN COMPOUNDS
PERCHLORATES
PROTONS
QUINONES
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
YIELDS