New 4-aryl-hydrazino- and 4-aryl-azo-quinoline derivs.

摘要

4-Arylhydrazino-quinolines of formula (I) and 4-arylazo-quinolines of formula (II) and the N-oxides and acid-addn. salts of (I) are new. R1-R4 = H, OH, NO2, halo, 1-4C alkyl, 1-4C alkoxy, 1-4C haloalkyl, 1-4C alkylthio, 1-4C haloalkoxy, 1-4C haloalkylthio or 2-5C alkoxyalkyl; R5, R6 = H, halo, 1-4C alkyl, 1-4C alkoxy, 1-4C haloalkoxy or 1-4C alkylthio; R7 = H, 1-4C alkyl, CHO, 2-5C alkanoyl or 2-5C alkoxycarbonyl; R8 = H, CHO, opt. halogenated 1-8C alkyl, 2-8C alkenyl, 2-8C alkynyl, 2-9C alkanoyl or 3-7C cycloalkyl; aryl or heteroaryl opt. substd. by 1-3 of NO2, halo, CN, 1-4C (halo)alkyl, 1-4C (halo)alkoxy, 1-4C alkylthio, mono and di(1-4C alkyl)amino, 1-4C alkylsulphonyl, 1-4C alkylsulphoxy (sic), 1-4C alkylsulphonyloxy, 2-5C alkanoyl, 2-5C alkanoyloxy, 2-5C alkoxycarbonyl, aryl or aryloxy,;or R7+R8 = a bond; R9 = aryl or heteroaryl opt. substd. by 1-3 of NO2, halo, CN, 1-4C (halo)alkyl, 1-4C (halo)alkoxy, 1-4C alkylthio, mono- and di(1-4C alkyl)amino, 1-4C alkylsulphonyl, 1-4C alkylsulphoxy (sic), 1-4C alkylsulphonyloxy, 2-5C alkanoyl, 2-5C alkanoyloxy, 2-5C alkoxycarbonyl, aryl and aryloxy, where aryl and aryloxy are opt. substd. by 1-3 of NO2, of halo, CN, 1-4C (halo)alkyl, 1-4C(halo)alkoxy, 1-4C alkylthio, mono- and di)1-4C alkyl)amino, 1-4C alkylsulphonyl, 1-4C alkylsulphoxy (sic), 1-4C alkylsulphonyloxy, 2-5C alkanoyl, 2-5C alkanoyloxy, 2-5C alkoxycarbonyl, aryl or aryloxy. Cpds. (I) with the following substits. are excluded (substits. not mentioned are H): R9 = phenyl, 4-chlorophenyl (an its N-oxide and HCl salt), 2,4-dichlorophenyl (and N-oxide and HCl salt), 2,4-dibromophenyl; R9 = 4-bromophenyl (HBr salt); R5 = Me, R7 = H or Me and R9 = phenyl; R2 ,R5 = Me, and R9 = phenyl; R1 = OMe, R5 = Me, R9 = phenyl (HCl salt); R2 = Me, R9 = 4-nitrophenyl(and N-oxide and HCl salt); R3 = Cl, R9 = 4-nitrophenyl or 4-chlorophenyl; R5 = Cl, R9 = 4-chlorophenyl or 2,4-dichlorophenyl, R3= 4-quinolyl (and di-N-oxide); R5 = Me, R9 = 4-quinolyl (di-N-oxide); Q, R9 = phenyl, 4-chlorophenyl, 4-bromophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl or 4-dimethylaminophenyl (and N-oxides); R2, R4 = OMe or OEt, R5 = Me, R7 = undefined, and R9 = phenyl; R5 = Ce (sic), Q, and R9 = phenyl, 4-chlorophenyl or 2,4-dichlorophenyl; R3 = Cl, Q, and R9 = phenyl; R5 = Me, R7 and R8 undefined, and R9 = phenyl; R5,R6 = Me, Q, R9 = phenyl, R1, R5 = Me, Q, R9 = phenyl; R2,R5 = Me, Q, R9 = phenyl; R5 = Me, Q, R9 = phenyl; R1,R3, R5 = Me, Q, R9 = phenyl; R2, R4, R5 = Me, Q, R9 = phenyl; Q = R7 and R8 are not defined.