4‐Amino‐3‐pyridiniochinolin‐2(1H)‐on‐chloride und 3,4‐Diaminochinolin‐2(1H)‐one

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...

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Veröffentlicht in:Chemische Berichte 1991-05, Vol.124 (5), p.1237-1241
Hauptverfasser: Gewald, Karl, Sch äfer, Harry, Bellmann, Peter, Müller, Heike
Format: Artikel
Sprache:eng
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Zusammenfassung: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‐selena‐diazolo[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.
ISSN:0009-2940
1099-0682
DOI:10.1002/cber.19911240542