Prinz, Helge and Burgemeister, Thomas and Wiegrebe, Wolfgang and Müller, Klaus (1996) Syntheses of anthracenones .2. Preparation of 1,8-dimethoxy-(dimethylanthralin) and 4,5-dihydroxy-9(10H)-anthracenone (isoanthralin): A revision. JOURNAL OF ORGANIC CHEMISTRY, 61 (8). pp. 2857-2860. ISSN 0022-3263, 1520-6904
Full text not available from this repository.Abstract
The reduction of 1,8-dimethoxyanthracenedione with zinc dust and aqueous ammonia gives a mixture of 1,8-dimethoxyanthracene and 4,5-dimethoxy-9(10H)-anthracenone, rather than the isomeric 1,8-dimethoxy-9(10H)-anthracenone (dimethylanthralin). This isomer was obtained exclusively using SnCl2 in HCl and acetic acid as reducing agent at room temperature. The structure was confirmed to exist as the tautomeric 1,8-dimethoxy-9-hydroxyanthracene. Furthermore, the reduction of 1,8-diacetoxyanthracenedione with SnCl2 in HCl and acetic acid leads to 1,8-dihydroxy-(10H)-anthracenone (anthralin) rather than 4,5-dihydroxy-9(10H)-anthracenone (isoanthralin), which was prepared by ether cleavage of 4,5-dimethoxy-9(10H)-anthracenone. In light of these findings some biological studies on antipsoriatic anthracenones have to be reconsidered.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ANTHRALIN DERIVATIVES; INHIBITION |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 02 Nov 2023 06:03 |
| Last Modified: | 02 Nov 2023 06:03 |
| URI: | https://pred.uni-regensburg.de/id/eprint/51774 |
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