Heterocyclization of N-substituted 2-amino-3-acetylenyl-1,4-naphthoquinones

Journal Article · Fri Nov 01 04:00:00 EST 1985 · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF01142788· OSTI ID:7032183

Romanov, V S; Moroz, A A; Shvartsberg, M S

The authors have found that 1,2-disubstituted benzindolequinones (I) can be prepared via the base-catalyzed cyclization of 2-amino-3-acetylenyl-1,4-naphthoquinones (II). The reactions are carried out with heating in pyridine or mesitylene in the presence of catalytic amounts of KOH (1.5-6 wt.%, relative to (II)). The cyclization of IIg was carried out using PhC = CCu instead of KOH as catalyst. The product yields of (I) ranged from 25-82% and are presented. It is shown that 2-N-acetylamino-3-acetylenyl-1,4-naphthoquinones are cyclized in neutral solvents at 80-110 C to the corresponding 2-substituted 4-N-acetylamino-5-oxonaphtho (4,3-b)furans.

• Research Organization: Institute of Chemical Kinetics and Combustion, Siberian Branch, Novosibirsk
• OSTI ID: 7032183
• Journal Information: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 34:5,PT.2; ISSN BACCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
ALKYLATED AROMATICS
AROMATICS
AZINES
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DEHYDROCYCLIZATION
DIAGRAMS
DISPERSIONS
EMISSION SPECTRA
FURANS
HETEROCYCLIC COMPOUNDS
HIGH TEMPERATURE
HYDROCARBONS
KINETICS
MESITYLENE
MIXTURES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
POTASSIUM COMPOUNDS
POTASSIUM OXIDES
PYRIDINES
QUANTITY RATIO
QUINONES
REACTION KINETICS
SOLUTIONS
SPECTRA
SPECTROSCOPY
SYNTHESIS
YIELDS