1979 Volume 99 Issue 10 Pages 1021-1026
A convenient synthesis of 3-substituted quinolizidines was developed. Cyclization of 3-[2-(2-chloroethyl) piperidin-1-yl] propionitrile (10) with a base afforded 3-cyanoquinolizidines (13a and 13b) in good yield, which have been transformed to 5-alkyl-3-diarylmethylenequinolizidinium bromides (5), novel antispasmodics. 3-Cyanoquinolizidines (13a and 13b) were converted to 3-ethoxycarbonyl-(14a and 14b), 3-benzoyl-(17a and 17b) and 3-(2-thenoyl)-quinolizidines (18a and 18b), respectively. 3-Ethoxycarbonyl-(14a and 14b) and 3-benzoyl-quinolizidines (17a and 17b) were also obtained by cyclization of the chloroester (11) and the chlorobenzoyl (12), respectively. The stereochemistry of the 3-substituted quinolizidines synthesized here was determined.
