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

Journal Article · · J. Org. Chem. USSR (Engl. Transl.); (United States)
OSTI ID:6035660
; ;

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), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:12; 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
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
ALKALOIDS
AMINES
BIOLOGICAL EFFECTS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACID ESTERS
CARBOXYLIC ACID SALTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORIDES
CHLORINE COMPOUNDS
COUPLING
COUPLING CONSTANTS
DEHYDROCYCLIZATION
ELECTRONIC STRUCTURE
ESTERS
EVEN-ODD NUCLEI
HALIDES
HALOGEN COMPOUNDS
HYDROGEN 1
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
HYPERFINE STRUCTURE
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MASS SPECTRA
MOLECULAR STRUCTURE
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIMES
REDUCTION
SPECTRA
SPECTRAL SHIFT
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
TIN CHLORIDES
TIN COMPOUNDS
TIN HALIDES
ULTRAVIOLET SPECTRA