Process for the production of metal complexes of isoindoline azines

Claim 1

A process for the manufacture of a 1:1 metal complex of an azine of formula I ##STR78## wherein the ring A is unsubstituted or is substituted by 2 to 4 chlorine atoms, by 1 to 2 alkyl or alkoxy groups having each 1 to 4 carbon atoms, by a phenoxy, by phenyl, by nitro, by benzoylamino or by a C 2-6 -alkanoylamino group, R 1 is a hydrogen atom or a methyl group, R 2 is a radical selected from the group consisting of ##STR79## Y is the radical of a heteroaryl amine selected form the group consisting of 2-aminothiophene, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-5-methylsulfonylthiazole, 2-amino-5-cyanothiazole, 2-amino-4-methyl-5-nitrothiazole, 2-amino-4-methylthiazole, 2-amino-4-phenylthiazole, 2-amino-4-(4'-chloro)-phenylthiazole, 2-amino-4-(4'-nitro)-phenylthiazole, 2-aminopyrazole, 3-amino-1-phenylpyrazole, 3-aminoindazole, 5-methylsulfonyl-2-aminothiazole, 5-benzoyl-2-aminothiazole, 4-aminoimidazole, 4,5-dicyano-2-aminoimidazole, 4,5-diphenyl-2-aminothiazole, 2-amino-3,4-thiadiazole, 2-amino-3,5-thiadiazole, 3-amino-1,2,4-triazole, 2-amino-3,4-oxadiazole, 3-aminopyridine, 2-aminopyridine-N-oxide, 2-amino-benzthiazole, 2-amino-6-chlorobenzthiazole, 2-amino-6-methyl-benzthiazole, 2-amino-6-methoxybenzthiazole, 2-amino-6-chloro-4-nitrobenzthiazole, 2-amino-6-bromo-4-cyanobenzthiazole, 2-amino-6-cyano-4-methylbenzthiazole, 2-amino-6-methyl-4-nitrobenzthiazole, 2-amino-6-methoxy-4-nitrobenzthiazole, 2-amino-6-butoxy-4-chlorobenzthiazole, 2-amino-4-chloro-5-methoxybenzthiazole, 2-amino-4-bromo-6-methoxybenzthiazole, 2-amino-4,6-dichlorobenzthiazole, 2-amino-4,6-dibromobenzthiazole, 2-amino-4-methyl-6-(trifluoromethyl)-benzthiazole, 2-amino-4-methyl-6-propionylbenzthiazole, 2-amino-4-chloro-6-methylsulfonyl-benzthiazole, 3-aminobenzisothiazole, 3-amino-5-chloro-benzisothiazole, 2-amino-3-cyanotetrahydrobenzthiaphene, 2-amino-benzimidazole, 2-amino-6-chlorobenzimidazole, 2-amino-6-bromo-benzimidazole, 2-amino-6-methylbenzimidazole, 2-amino-6-methoxy-benzimidazole, 2-amino-6-ethoxybenzimidazole, 2-amino-6-methylsulfonyl-benzimidazole, 2-amino-6-acetylaminobenzimidazole, 2-aminopyridine, diaminophthalazine, 2-amino-4-hydroxyquinoline, 2,6-diaminopyridine and 2-amino-4,5-dimethylthiazole, or Y is a group of the formula ##STR80## R' is --CONH 2 , --CSNH 2 or a radical selected from the group consisting of ##STR81## Y 1 is --O--, --S-- or --NH--, Y 2 is a hydrogen atom, a carboxyl or carbamoyl group, an alkoxycarbonyl or alkylcarbamoyl group containing 2 to 6 carbon atoms, a phenylcarbamoyl group which is unsubstituted or substituted in the phenyl moiety by halogen atoms, alkyl or alkoxy groups containing 1 to 4 carbon atoms, Y 3 is a hydrogen or a halogen atom, a methoxy, nitro or cyano group, X 1 is a hydrogen, chlorine or bromine atom, a nitro, trifluoromethyl, carbamoyl or sulfamoyl group, an alkyl, alkoxy or alkylsulfamoyl group of 1 to 4 carbon atoms, an alkanoylamino, alkylcarbamoyl or alkoxycarbonyl group of 2 to 6 carbon atoms, a phenoxy, phenylcarbamoyl or phenylsulfamoyl group which is unsubstituted or substituted by chlorine or bromine atoms or methyl groups, X 2 is a hydrogen, chlorine or bromine atom, an alkyl or alkoxy group of 1 to 4 carbon atoms, R 6 is a cyano, carbamoyl or alkoxycarbonyl group of 2 to 6 carbon atoms, R 7 is a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, a phenyl or hydroxy group, Q is a methyl group or an alkoxycarbonyl group containing 2 to 5 carbon atoms or a carbamoyl group, Z is --O-- or --S-- and V is --O--, --S-- or --NH--, which process comprises reacting a compound of the formula II ##STR82## wherein R 3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R 4 is an alkyl group having 1 to 6 carbon atoms, or ##STR83## is the radical of the formula ##STR84## wherein X 1 and X 2 are as defined above, or R 3 and R 4 together with the N-atom to which they are attached form a pyrrolidino, piperidino or morpholino radical, with a hydrazone of the formula II ##STR85## in the presence of a transition metal donor and in a polar organic solvent, at temperatures above 100° C., Y, R 1 and R 2 having the meanings given under formula I, and the ring A being as defined under formula I.