Chemical and Pharmaceutical Bulletin p. 3067 - 3071 (1992)
Update date:2022-07-30
Topics:
Kawano
Kurimoto
Hatanaka
Ueda
4-(N,N-Dialkylamino)-2-phenyl-2-(2-pyridyl)butanenitriles (10, 11 and 12) and 5-(N,N-dimethylamino)-2-phenyl-2-(2-pyridyl)pentanenitrile (13) react with ethyl chloroformate, via a cyclization-N-dealkylation process, to give indolizinium and quinolizinium salts (1 and 2). Compounds 1 and 2 are also obtained by reaction of the alcohol derivatives 14 and 15 with thionyl chloride. Reaction of 2-phenyl-2-(2-pyridyl)ethanenitrile (9) in the presence of potassium hydroxide in dimethyl sulfoxide, leading to [2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl]methylsulfoxide (21), is also described.
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