[Reactions of N-quaternary 1-phenyl-3,4-dihydroisoquinolinium compounds with nucleophiles - products and their isomerism - part 1].
Variously substituted 1-phenyl-3,4-dihydroisoquinolinium compounds were prepared, in order to study their reactions with hydroxide ions concerning ring-chain isomerism of their products. Thereby was observed a dependence on the electrophilic properties of C-1 for forming the pseudo-bases and a ring opening tendency to the amino ketones by electron-withdrawing substituents at the nitrogen atom. Moreover steric effects caused by voluminous substituents in 1- and 2-positions also importantly affected the isomeric distribution. So the N-ethyl derivatives showed an enhanced dissociation of the hemiaminal to the quaternary iminium base. From a solution of the dihydroisoquinolinium salt 35 in [D6]DMSO after addition of NaOD until pH 10 resulted an equilibrium of the quaternary iminium base 36q, the pseudo-base 36a and the amino ketone 36b. These species were detected and assigned by NMR measurements.
Möhrle
H
H
Institut für Pharmazeutische Chemie, Heinrich-Heine-Universität, Düsseldorf, Germany. h.moehrle@uni-duesseldorf.de
Breves
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D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004563:Electrochemistry; D006859:Hydrogen / Q000737:chemistry; D007202:Indicators and Reagents; D007536:Isomerism; D007546:Isoquinolines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen / Q000737:chemistry
D007202:Indicators and Reagents; D007546:Isoquinolines; D006859:Hydrogen; D009584:Nitrogen; D004121:Dimethyl Sulfoxide
Reaktionen von N-quartären 1-phenyl-3,4-dihydroisochinolinium-verbindungen mit nucleophilen-produkte und ihre isomerie--1. Mitt.