ES437192A1 - Procedure for the preparation of new derivatives of quinolein. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

Procedure for the preparation of new quinoline derivatives of the general formula I, **(See formula)** wherein A represents a group of the formula (see formula), wherein R1 signifies a hydrogen atom, a straight or branched chain alcohol radical of 1 to 6 carbon atoms, which may be substituted with a hydroxy, methoxy group, carboxy, cyano, dimethylaminocarbonyl, morpholinocarbonyl or carbalkoxy of 2 to 6 carbon atoms, a straight chain or branched aliphatic acyl radical of 1 to 12 carbon atoms optionally substituted with a methoxy group, a benzoyl radical optionally substituted with an atom of halogen, a carbalkoxy radical of 2 to 7 carbon atoms, a carbocycloalkoxy radical of 4 to 7 carbon atoms, a benzyl radical optionally substituted with a methyl group, a phenylsulfonyl radical optionally substituted with a methyl group or with a halogen atom, an alkenyl radical of 2 to 6 carbon atoms, a phenyl, trifluoroacetyl, amidino, amido, thioamido, phenoxycarbonyl, benoyloxycarbonyl or methylsulfonyl group; R2 signifies a hydroxyl group, an acyloxy radical of 1 to 3 carbon atoms, an alcoholyloxycarbonyloxy radical of 2 to 4 carbon atoms, an amino, dimethylamino, morpholino group or a halogen atom; R3 signifies a hydrogen or halogen atom, a hydroxy or carboxy group, a straight or branched chain alcohol radical of 1 to 6 carbon atoms, a cycloalkoxy radical of 3 to 6 carbon atoms, an alkoxy group of 1 to 3 carbon atoms, which may be substituted with a phenyl or carbalkoxy radical of 2 to 4 carbon atoms, a carbalkoxy radical of 2 to 4 carbon atoms, a hydroxymethyl, phenyl, phenoxy, amino, pyrrolidine or morpholino group; R4, R5, and R6, which may be the same or different, signify hydrogen or halogen atoms, methyl, hydroxy, methoxy, cyano, amino, nitro, trifluoromethyl, carboxy, acetyl, carbalkoxy groups of 2 to 4 carbon atoms or two of the radicals R4, R5 or R6 together signify the methylenedioxy group; as well as give the 6-N-oxides of these and their salts by the addition of acid physiologically compatible with organic or inorganic acids, characterized in that a compound of the general formula II is reacted **(See formula)** wherein R3, R4, R5, R6 and A are as defined at the beginning, in the presence of an acid derivative capable of reacting and, if desired, by subsequent separation of the acyl radical or carbonic acid ester, and in case desired, if according to the procedure a compound of the general formula I is obtained, in which at least one of the radicals R1 to R6 contains a hydrogen atom capable of reacting, this is transformed by alkylation, acylation and/or vinylation in the corresponding compound of the general formula I, and/or a compound of the general formula I is obtained, in which R1 represents an alcoholic or aralcohyl group, this is transformed by reaction with a chloroformic acid ester into a compound of the general formula I, in which R1 means an alkoxycarbonyl, cycloalkoxycarbonyl or phenyloxycarbonyl radical, and/or a compound of the general formula X is obtained, in which R1 represents one of the acyl radicals mentioned in the com enzo and/or represents a carboxyl group, this is transformed by reduction in the corresponding compound of the general formula I, in which R1 represents an alcohol radical and/or R3 represents a hydroxymethyl group, and/or a compound of the general formula I in which R1 means one of the organic or inorganic acyl or carbalkoxy radicals mentioned at the beginning, this is transformed by an oxidizing agent into the corresponding 6-R-oxide, and/or a 6-N-oxide of general formula I, in which R2 does not represent any hydrogen atom and R3 represents a methyl group, this is transformed into a compound of general formula I, in which R3 represents the hydroxymethyl group, and/or a mixture is obtained of isomers of the general formula I, this is split into its Isomers, and/or a compound of the general formula I is obtained, this is transformed into its salts by the addition of acid physiologically compatible with organic or inorganic acids. (Machine-translation by Google Translate, not legally binding)