TY - JOUR
T1 - Synthesis of 2-Dialkylamino-6- and -7-hydroxy-5,8-dioxoquinolines
AU - Fleming, Wayne C.
AU - Pettit, George
PY - 1971/11/1
Y1 - 1971/11/1
N2 - A synthetic route to 2-substituted 6- and -7-hydroxy-5,8-dioxoquinolines has been evaluated. Reaction of 5,7-dinitro-8-hydroxycarbostyril (4) with phosphorus oxychloride followed by reaction with piperidine ormorpholine gave the 2-substituted 5,7-dinitro-8-quinolinols 5d and 5e. Catalytic hydrogenation, oxidation, and acid hydrolysis gave the corresponding 7-hydroxy-5,8-dioxoquinolines 9a and 9b. A similar sequence was used to proceed from 5-hydroxy-6,8-dinitrocarbostyril (12)i)ia2-chloro-6,8-dinitro-5-quinolinoI (13a) and 2-piperidino-6,8-dinitro-5-quinolinol (13b) to 2-piperidino-6-hydroxy-5,8-dioxoquinoline (14a).
AB - A synthetic route to 2-substituted 6- and -7-hydroxy-5,8-dioxoquinolines has been evaluated. Reaction of 5,7-dinitro-8-hydroxycarbostyril (4) with phosphorus oxychloride followed by reaction with piperidine ormorpholine gave the 2-substituted 5,7-dinitro-8-quinolinols 5d and 5e. Catalytic hydrogenation, oxidation, and acid hydrolysis gave the corresponding 7-hydroxy-5,8-dioxoquinolines 9a and 9b. A similar sequence was used to proceed from 5-hydroxy-6,8-dinitrocarbostyril (12)i)ia2-chloro-6,8-dinitro-5-quinolinoI (13a) and 2-piperidino-6,8-dinitro-5-quinolinol (13b) to 2-piperidino-6-hydroxy-5,8-dioxoquinoline (14a).
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U2 - 10.1021/jo00822a004
DO - 10.1021/jo00822a004
M3 - Article
C2 - 5132691
AN - SCOPUS:0015232736
SN - 0022-3263
VL - 36
SP - 3490
EP - 3493
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -