New 1,7-diaza:perylene and its derivs. - prodn. from di:amino anthra-quinone in few stages and use e.g. as orange fluorescent marker

摘要

The following new cpds. are claimed 1,7-diazaperylene, benzo(de)isoquinolin(1,8-gh)quinoline of formula (I); 2,8-dihydroxy-1,7-diazaperylene (II); 2,8-dimethoxy-1,7-diazaperylene (III); 2,8-di(2-pyrimidyl)-1,7-diazaperylene (IV); and 1,7-diazaperylenes of formula (V). In formulae R1-6 = H; or up to 4 of R1-6 may = isocyclic aromatic gps., pref. mono- to tetracyclic, esp. mono- or bicyclic gps.; heterocyclic aromatic gps., pref. mono- to tricyclic gps., which may be purely heterocyclic ro contain a heterocyclic ring and one or more annelated benzene rings; halogen; linear or branched alkyl; OR10 with R10 = H, (cyclo)alkyl or (het)aryl; CN; -N(R8)(R9) (R8 and R9 = H, (cyclo)alkyl or (het)aryl; or R8 and R9 with one of R2-4 = a 5-6-membered (hetero)ring); -COR7 (R7 = alkyl, aryl, benzyl or heterocyclyl); -N(R11)-COR7 (R11 = H, alkyl, benzyl or phenyl; -N(R10)-COOR7; -N(R10)CON(R8)(R9); -NHSO2R7; -SO2R7 or -SOR7; -CON(R8)(R9); -SO2N(R8)(R9); -N=N-R12 (R12 = the radical of a coupling component or phenyl); -OCOR7; or -OCONHR7; and all the susbtits. may ahve a wide variety of substits. (The detailed definitions cover 4 pages). USE/ADVANTAGE - (I-V) can be produced easily in few stages (e.g. (I) can be prepd. from technical 1,5-diaminoanthraquinone in 5 stages, the last involving Meerwein arylation). (I) and its derivs. can be used e.g. as fluorescent marker, which absorb short-wave light and fluoresce long-wave, orange light.