ONE-POT CLAISEN REARRANGEMENT O-METHYLATION/ALKENE ISOMERIZATION IN THE SYNTHESIS OF ORTHO-METHOXYLATED PHENYLISOPROPYLAMINES/

Authors
WALDMAN SR MONTE AP BRACEY A NICHOLS DE
Citation
Sr. Waldman et al., ONE-POT CLAISEN REARRANGEMENT O-METHYLATION/ALKENE ISOMERIZATION IN THE SYNTHESIS OF ORTHO-METHOXYLATED PHENYLISOPROPYLAMINES/, Tetrahedron letters, 37(44), 1996, pp. 7889-7892
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
44
Year of publication
1996
Pages
7889 - 7892
Database
ISI
SICI code
0040-4039(1996)37:44<7889:OCROII>2.0.ZU;2-J
Abstract
An improved synthesis of a potent serotonin agonist la and its novel d erivative Ib is described, making use of a Claisen rearrangement whose unstable phenolic product is methylated and isomerized in sire. This method may be of general use in the synthesis of o-methoxylated phenet hylamine derivatives. The synthesis also includes an unusual, one pot demethylation/primary alcohol bromination with boron tribromide. Copyr ight (C) 1996 Elsevier Science Ltd