Tetrahydroacridin-9-ones, 9-chlorotetrahydroacridines, 9-amino-tetrahydroacridines and 9-(pyrazol-1-yl)-tetrahydroacridines derived from chiral cyclanones.
A series of tetrahydroacridines related to tacrine have been synthesized starting from 3-methylcyclohexananone, menthone, pulegone, carvone and dihydrocarvone (both racemic and chiral). In many cases, the yields and purity of the compounds have been improved by the use of a microwave oven. These compounds have been characterized by (1)H and (13)C NMR data. To establish their relative configuration, the structure of (1R,4R)-(+)-9-chloro-1-methyl-4-isopropyl-1,2,3,4-tetrahydroacridine (cis-10b), derived from (2S,5R)-(-)-menthone, has been determined by X-ray. The chemical shifts of cis-10b and trans-10b have been calculated at the GIAO/B3LYP/6-31G* level and compared successfully with the experimental data.
Laboratoire de valorisation de la chimie fine, faculté de sciences et techniques de St. Jérôme, Université d'Aix-Marseille III, avenue Escadrille Normandie-Niémen, 13397 Marseille cédex 20, France.
Aline
A
Frideling
Robert
R
Faure
Jean-Pierre
JP
Galy
Ahmed
A
Kenz
Ibon
I
Alkorta
José
J
Elguero
D018360:Crystallography, X-Ray; D003510:Cyclohexanes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013619:Tacrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D003510:Cyclohexanes; D007659:Ketones; D013619:Tacrine