Prinz, Helge and Wiegrebe, Wolfgang and Müller, Klaus (1996) Syntheses of anthracenones .3. Revised preparative route to 10-benzoyl-1,8-dihydroxy-9(10H)-anthracenones. JOURNAL OF ORGANIC CHEMISTRY, 61 (8). pp. 2861-2864. ISSN 0022-3263, 1520-6904
Full text not available from this repository.Abstract
The acylation of anthralin (1,8-dihydroxy-9(10H)-anthracenone) with acetylsalicylic acid chloride in toluene and collidine was found to give the O-acylated product, rather than 10-(acetylsalicyl)-anthralin. A procedure is described for benzoylation of anthralin in the 10-position which involves reaction of 1,8-diacetoxy-9(10H)-anthracenone with benzoyl chloride and sodium hydride in THF followed by hydrolysis of an intermediate enol ester. Furthermore, when benzoyl chloride and DMF were used for the acylation of anthralin, a Vilsmeier-type reaction was observed leading to a novel enamine derivative of anthralin which was hydrolyzed or benzoylated to an enol or enol ester, respectively.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DITHRANOL; ANTHRALIN |
| 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 06:04 |
| Last Modified: | 02 Nov 2023 06:04 |
| URI: | https://pred.uni-regensburg.de/id/eprint/51775 |
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