4-AMINO-3-PYRIDINIOQUINOLIN-2(1H)-ONE CHLORIDES AND 3,4-DIAMINOQUINOLIN-2(1H)-ONES

N-(Chloroacetyl)anthranilonitriles 1 react with the pyridines 2 to form the 4-amino-3-pyridinioquinolin-2(1H)-one chlorides 4, which are converted into the pyrido[1',2':1,2]imidazo[5,4-c]-quinolin-6(5H)-ones 6 in the presence of sodium hydroxide or by cyclooxidation with bromine. Treatment of 4 with hydrazine hydrate yields the 3,4-diaminoquinolin-2(1H)-ones 9. Analogously to other o-diamines the substituted imidazo[4,5-c]quinolinones 12, the pyrazino[2,3-c]quinolinones 13, 14, the 1,2,5-thiadiazolo[3,4-c]quinolin-4-one 15a and the 1,2,5-selenadiazolo[3,4-c]quinolin-4-one 15b are obtainable from 9a. With chloroacetyl chloride 9a provides the oxazino[2,3-b]quinolin-2-one 11.