The intramolecular Schmidt reaction of azides with tertiary alcohols: Synthesis of 5-(α-naphthyl)- and 5-(β-naphthyl)indolizidines as potential dopamine analogs and non-opiate antinociceptive agents

Article abstract of DOI:10.1016/0040-4020(96)00723-5

Intramolecular Schmidt reaction of the azido alcohols 9, 11, and 12 afforded the 5-naphthylindolizidines 10, 13, and 14, respectively. The naphthylmethylamine subunit present in each has an amine and a π-system oriented in a fashion similar to the β-phenethylamine subunit of dopamine and many of its agonists and antagonists. These analogs also closely resemble the bicyclic tertiary amines 8, which have recently been found to exhibit non-opiate analgesic activity. Testing of 10, 13, and 14 for dopaminergic activity is described.