Dihydroquinoline derivatives of antioxidant activity and a process for the preparation thereof
AssigneeMaterial Ksz.
InventorsVilmos Bar, Jeno Mercz, Janos Szvoboda, Zsuszanna B. Pollak, Jakab Matyas
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Abstract
This invention relates to novel condensation products of aldehydes and tri- or tetramethyl-1,2-dihydroquinolines of antioxidant activity, as well as to a process for the preparation of such products. The novel compounds are nontoxic, exert their activity both in living organisms and in inanimate objects, and can be used in the chemical and food industry, as well as for therapeutical purposes.
Claims11
A process for the preparation of a nontoxic dihydroquinoline-aldehyde condensation product, having the formula /I/ ##STR2## wherein R represents hydrogen or a lower alkyl group of 1 to 4 carbon atoms,
- R.sub.1 represents hydrogen or a methyl group which may be attached in any of the free positions to the ring system, with the exception of position 6,
- n is 1, 2 or 3,
- or the addition salts of these compounds with nontoxic acids, comprising the steps of reacting the heterocycle 2,2,4-trimethyl-1,2-dihydroquinoline or a derivative thereof having a further methyl group but being unsubstituted in the 6-position, or an acid addition salt of these compounds with 0.5 to 1.0 molar equivalents of an aldehyde of the formula
- R -- CHO
- wherein R has the same meaning as defined above in the presence of a solvent and of a catalyst, said catalyst being an acid or a metal halide of acidic character, at temperatures between room temperature and the boiling point of the reaction mixture, and removing any unreacted starting compound and catalyst where toxic from the reaction mixture, at least one pair of adjacent heterocycles being joined through said aldehyde at 6, 6 positions of same.
Dependencies are inferred from the claim text.