Patent EP-0217214-A1 (EP)
Inventor: FUERSTENWERTH HAUKE DR
IPC: C09B57/00
Filed: 1986-09-15
Abstract: 1. 2,4-Dioxopyrrolo[2,3-c]pyrroles which in one of their tautomeric forms conform to the formula  see diagramm : EP0217214,P20,F13  in which R1 , R2 signify phenyl, biphenylyl, naphthyl or a heterocyclic aromatic radical, which contains 1, 2, 3 or 4 five-, six- or seven-membered rings of which at least one contains 1, 2 or 3 hetero atoms from the series N, O, S, and wherein, the radicals mentioned for R1 , R2 can be substituted by halogen, -CN, -R5 , OR6 , SR6 , -N(R7 )(R8 ), -COOR9 , -N(R10 )COR9 , -N(R6 )COOR9 , N(R6 )CON(R7 )(R8 ), -NHSO2 R9 , -SO2 R9 , -SOR9 , -SO2 OR9 , -CON(R7 )(R8 ), -SO2 N(R7 )(R8 ), -N=N-R11 , -OCOR9 and -OCONHR9 , R3 , R4 stand for hydrogen, C2 -C18 -alkenyl and C2 -C18 - alkynyl, which can each be substituted by halogen, -CN, -OCOR9 , -OR7 , -COOR9 , -SR7 , -CON(R7 )(R8 ) and -OCONHR9 , epoxyethyl, phenyl and naphthyl, which can each be substituted by F, Cl, -Br, -NO2 , -CN, -CF3 , C1 -C18 -alkyl, C1 -C18 -alkoxy, phenyl, phenoxy, C1 -C6 -alkoxycarbonyl and phenoxycarbonyl, -R5 , -COR6 , -CON(R7 )(R8 ),  see diagramm : EP0217214,P21,F1  or a radical of the formula  see diagramm : EP0217214,P21,F2  and R5 signifies C1 -C18 -alkyl or C3 -C7 -cycloalkyl which can each be substituted by halogen, -CN, -OCOR9 , -OR7 , -COOR9 , -SR7 , -CON(R7 )(R8 ) and -OCONHR9 , R6 , R7 , R8 signify hydrogen, C1 -C18 -alkyl, cyclopentyl and cyclohexyl which can each be substituted by Cl, Br, F, -CN, -OH, mono C1 -C4 -alkylamino, di-C1 -C4 -alkylamino, optionally Cl-, Br-, F-, C1 -C6 -alkyl-or C1 -C6 -alkoxy-substituted phenyl or naphthyl, or by heterocyclic aromatic radicals of a 5- or 6-membered heterocyclic ring system which incorporates 1 or 2 hetero atoms from the series O, N, S and onto which a benzene ring can be fused, phenyl, naphthyl, phenyl-C1 -C4 -alkyl and naphthyl-C1 -C4 -alkyl which can each be substituted by Cl, Br, F, C1 -C18 -alkyl or C1 -C18 -alkoxy, the radical of a 5- or 6-membered heterocyclic ring which incorporates 1, 2 or 3 hetero atoms from the series O, N, S and onto which a benzene ring can be fused, or R7 and R8 in the group -CON(R7 )(R8 ) together with inclusion of the N atom form a 5- or 6-membered heterocyclic ring, R9 signifies C1 -C18 -alkyl, cyclopentyl, cyclohexyl, phenyl-C1 -C4 -alkyl, naphthyl-C1 -C4 -alkyl, phenyl, naphthyl, or the radical of a 5- or 6-membered heterocyclic ring which incorporates 1, 2 or 3 hetero atoms from the series O, N, S and onto which a benzene ring can be fused, it being possible for the radicals mentioned for R9 to be substituted like the corresponding radicals R7 , R8 , R10 signifies hydrogen, -COR9 or R7 , R11 signifies the radical of a coupling component from the benzene, naphthalene, acetoacetic anhydride, pyrazole or pyridone series or a phenyl radical which is optionally substituted by Cl, Br, F, C1 -C18 -alkyl and C1 -C18 -alkoxy, R12 signifies hydrogen, C1 -C8 -alkyl, optionally F-, Cl-, Br-, NO2 -, CN-, CF3 -, C1 -C18 -alkyl-, C1 -C18 -alkoxy-, phenyl-, phenoxy-, C1 -C6 - alkoxycarbonyl- and phenoxycarbonyl-substituted phenyl or naphthyl, R13 stands for hydrogen or can take on the meanings of R3 , R4 except the radical of the formula Ia, R14 stands for a divalent saturated or unsaturated aliphatic bridge member having 1-8 C atoms, a phenylene or xylylene radical or a radical of the formulae  see diagramm : EP0217214,P21,F3  and  see diagramm : EP0217214,P21,F4  where R15 signifies a C1 -C10 -alkylene, a phenylene, toluylene or naphthylene radical and A stands for a radical of the formula  see diagramm : EP0217214,P21,F5  in which R16 denotes cyano, C1 -C6 -alkoxy-C1 -C6 -alkoxy-carbonyl, carbamoyl which is optionally substituted by C1 -C6 -alkyl, benzyl, naphthyl or phenyl, it being possible for phenyl, benzyl, naphthyl to be substituted by chlorine, bromine, C1 -C6 -alkyl, C1 -C6 -alkoxy, nitro, trifluoromethyl, C1 -C6 -alkylcarbonyl, cyano, C1 -C6 -alkylamino, benzoylamino, phthalimidyl, carbamoyl, C1 -C6 -alkylcarbonyl ; benzoyl, C1 -C6 - alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl, it being possible for benzoyl, benzyl and phenoxy to be substituted by halogen, nitro, C1 -C6 -alkyl, C1 -C6 - alkylcarbonylamino, phthalimidyl or phenyl which is optionally substituted by halogen, nitro, cyano and trifluoromethyl or a radical of the formula  see diagramm : EP0217214,P22,F1  in which R17 , R18 signify hydrogen, C1 -C6 -alkyl, optionally halogen-, C1 -C6 -alkyl-, C1 -C6 -alkoxy- or nitro-substituted phenyl, alpha-naphthyl and beta-napthyl.