U ntersuchungen an q u a rtä re n P yridinium -Salzen, I I I 1
R eaktionen von quaterniertem Nikotinsäuream id m it starker BaseIn v estig atio n s of Q u atern ary P yridinium Salts, I I I R eactions of Q u a te rn ary S alts of N icotinam ide w ith S trong Bases
Quartäre Nicotinamid‐Salze 1 lagern sich auf Zusatz der äquimolaren Menge anionischer Base bekanntlich zu Cyclotetrakondensaten 3 zusammen. Es wird die Darstellung einiger Vertreter mit funktionellen Gruppen, die intramolekulare Reaktionen ermöglichen sollen, beschrieben.
Abstract Quinolinium Salts, Redox Reactions Quaternary salts of 3-quinolinecarboxamide and 3-quinolinecarbonitrile react after addition of ZnCl2 with ethanol (or 2-propanol) to the corresponding 1,4-dihydroquinoline and ethanol (or propanone). This hydride transfer can be achieved with aluminium-triisopropoxide, too. Lipophilic insertionproducts (4,5,7,8) react with ethanol (or 2-propanal) after ZnCl2 addition to quinolinium-alcoxides, and then to the 1,4-dihydro-quinoline and ethanal (or propanone).
Four molecules of quaternary salts of nicotinamide (1 and 4) form a chloroform-soluble condensation product of structure 2 and 5 by action of base under elimination of HX.
Aus 3‐Chinolincarboxamid‐Salzen 1 entstehen auf Zusatz der äquimolaren Menge Kalium‐tert‐butylat bei −45°C Cyclotetrakondensate 2, mit 1,2‐Dihydrochinolinstruktur.
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