THE INTRAMOLECULAR SCHMIDT REACTION OF AZIDES WITH TERTIARY ALCOHOLS - SYNTHESIS OF 5(ALPHA-NAPHTHYL)INDOLIZIDINES AND 5-(BETA-NAPHTHYL)INDOLIZIDINES AS POTENTIAL DOPAMINE ANALOGS AND NONOPIATE ANTINOCICEPTIVEAGENTS

Authors
PEARSON WH GALLAGHER BM
Citation
Wh. Pearson et Bm. Gallagher, THE INTRAMOLECULAR SCHMIDT REACTION OF AZIDES WITH TERTIARY ALCOHOLS - SYNTHESIS OF 5(ALPHA-NAPHTHYL)INDOLIZIDINES AND 5-(BETA-NAPHTHYL)INDOLIZIDINES AS POTENTIAL DOPAMINE ANALOGS AND NONOPIATE ANTINOCICEPTIVEAGENTS, Tetrahedron, 52(37), 1996, pp. 12039-12048
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
37
Year of publication
1996
Pages
12039 - 12048
Database
ISI
SICI code
0040-4020(1996)52:37<12039:TISROA>2.0.ZU;2-0
Abstract
Intramolecular Schmidt reaction of the azido alcohols 9, 11, and 12 af forded the 5-naphthylindolizidines 10, 13, and 14, respectively. The n aphthylmethylamine subunit present in each has an amine and a pi-syste m oriented in a fashion similar to the beta-phenethylamine subunit of dopamine and many of its agonists and antagonists. These analogs also closely resemble the bicyclic tertiary amines 8, which have recently b een found to exhibit non-opiate analgesic activity. Testing of 10, 13, and 14 for dopaminergic activity is described. Copyright (C) 1996 Els evier Science Ltd