Benzophenanthridines. III. Investigation of the rodionov-suvorov scheme. Synthesis of methyl 6-methyl-11,12-dihydrobenzo(c)phenanthridine-11-carboxylate

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

OSTI ID:6035660

Sladkov, V I; Maslennikova, L V; Suvorov, N N

The model compound of the benzo(c)phananthridine alkaloids, i.e., methyl 6-methyl-11,12-dihydrobenzo(c)phenanthridine-11-carboxylate, was synthesized from 1,3-diphenyl-1,2,2-propanetricarboxylic acid by the AD ..-->.. C ..-->.. B scheme. On the basis of the UV, IR, PMR, and /sup 13/C NMR spectra and also of the mass spectra it was demonstrated that the reduction of 3,3-diethoxycarbonyl-2-phenyltetral-1-one oxime by stannous chloride in acetic anhydride followed by Bischler-Napiralski cyclization leads to diethyl 6-methyl-11,12-dihydrobenzo(c)phenanthridine-11,11-dicarboxylate and not to the 4b,10b,11,12-tetrahydro derivatives as suggested earlier.

• OSTI ID: 6035660
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 21:12; Other Information: Translated from Zh. Org. Khim.; 21: No.12, 2594-2600(Dec 1985)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
ALKALOIDS
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
OXIMES
DEHYDROCYCLIZATION
REDUCTION
TIN CHLORIDES
CATALYTIC EFFECTS
BIOLOGICAL EFFECTS
CARBON 13
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACID SALTS
CHEMICAL SHIFT
COUPLING CONSTANTS
ELECTRONIC STRUCTURE
HYDROGEN 1
HYPERFINE STRUCTURE
INFRARED SPECTRA
J-J COUPLING
MASS SPECTRA
MOLECULAR STRUCTURE
NMR SPECTRA
SPECTRAL SHIFT
ULTRAVIOLET SPECTRA
AMINES
CARBON ISOTOPES
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COUPLING
ESTERS
EVEN-ODD NUCLEI
HALIDES
HALOGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
INTERMEDIATE COUPLING
ISOTOPES
LIGHT NUCLEI
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SPECTRA
STABLE ISOTOPES
TIN COMPOUNDS
TIN HALIDES
400201* - Chemical & Physicochemical Properties
640302 - Atomic
Molecular & Chemical Physics- Atomic & Molecular Properties & Theory