Synthesis and Some Reactions of 6H-Indolo[2,3-b]quinoxalines

6 H -Indolo[2,3- b ]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with o -phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrat...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-12, Vol.56 (12), p.2104-2108
Main Authors: Shulga, S. I., Shulga, O. S.
Format: Article
Language:English
Subjects:
Alkylation
Chemical synthesis
Chemistry
Chemistry and Materials Science
Dimethyl sulfate
Hydrobromic acid
NMR
Nuclear magnetic resonance
Organic Chemistry
Perchlorates
Phenylenediamine
Potassium ferricyanide
Quinoxalines
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Summary:6 H -Indolo[2,3- b ]quinoxalines were synthesized by condensation of isatin and 5-nitroisatin with o -phenylenediamine. The alkylation of the title compounds with dimethyl sulfate gave the corresponding quaternary salts which were converted to perchlorates and oxidized with potassium hexacyanoferrate(III) to previously unknown 5-methyl-6 H -indolo[2,3- b ]quinoxalin-3-one and its 9-nitro derivative. Treatment of 6 H -indolo[2,3- b ]quinoxalin-3-ones with dimethyl sulfate afforded 3-methoxyindoloquinoxalinium salts which were demethylated by the action of hydrobromic acid at 130–140°C. The structure of the isolated compounds was confirmed by IR and NMR spectra and elemental analyses.
ISSN:1070-4280
1608-3393
DOI:10.1134/S107042802012009X