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Imidazoline ring cleavage in 1,3,6,10-tetraazatetracyclo-(7. 3. 1. 0/sup 2,7/. 0/sup 6,13/)trideca-4,11-dienes, leading to the formation of diquinoxalino(1,2-. cap alpha. :2',3'-d)pyrrole derivatives

Journal Article · · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)
DOI:https://doi.org/10.1007/BF00546741· OSTI ID:6961615
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Dibenzo(d,k)-1,3,6,10-tetraazatetracyclo(7.3.1.0/sup 2,7/.0/sup 6,13/) trideca-4,11-dienes undergo addition reactions at the C/sub (2)/ carbon atom with alcohols and thiols, accompanied by cleavage of the C-N bond of the imidazoline ring, to generate diquinoxalino(1,2-..cap alpha..:2',3'-d)pyrrole derivatives. /sup 1/H NMR spectra were recorded on Perkin-Elmer R 12B (60 MHz) and Bruker WH-90 spectrometer for CDCl/sub 3/ solutions at 40/sup 0/C and with TMS as internal standard. /sup 13/C NMR spectra were obtained on a Bruker WH-90 (22.62 MHz) spectrometer. /sup 13/C chemical shifts were measured relative to solvent signals (deltaCDCl/sub 3/ 77.0 ppm). /sup 13/C NMR spectra of compounds IIa and g were taken using full spin-spin carbon-proton decoupling. In order to measure SSCC the spectrum was recorded both with proton coupling and also with selective decoupling of individual protons and their attached /sup 13/C carbon nuclei.

Research Organization:
S. M. Kirov Ural Polytechnical Institute, Sverdlovsk (USSR)
OSTI ID:
6961615
Journal Information:
Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Journal Issue: 4 Vol. 23:4; ISSN CHCCA
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
ALCOHOLS
AZOLES
CARBON 13
CARBON ISOTOPES
CHEMICAL BONDS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORINATED ALIPHATIC HYDROCARBONS
CHLOROFORM
COHERENT SCATTERING
CONFORMATIONAL CHANGES
COUPLING
COUPLING CONSTANTS
DEHYDROCYCLIZATION
DEUTERIUM COMPOUNDS
DIENES
DIFFRACTION
EVEN-ODD NUCLEI
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN 1
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
IMIDAZOLES
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOMERIZATION
ISOTOPE EFFECTS
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MULTIPLETS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POLYENES
PYRROLES
SCATTERING
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
THIOLS
ULTRAVIOLET SPECTRA
X-RAY DIFFRACTION