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Prinz H, Burgemeister T, Wiegrebe W, et al. Syntheses of Anthracenones. 2. Preparation of 1,8-Dimethoxy- (Dimethylanthralin) and 4,5-Dihydroxy-9(10H)-anthracenone (Isoanthralin): A Revision. J Org Chem. 1996;61(8):2857-2860doi: 10.1021/jo952036t.
Prinz, H., Burgemeister, T., Wiegrebe, W., & Müller, K. (1996). Syntheses of Anthracenones. 2. Preparation of 1,8-Dimethoxy- (Dimethylanthralin) and 4,5-Dihydroxy-9(10H)-anthracenone (Isoanthralin): A Revision. The Journal of organic chemistry, 61(8), 2857-2860. https://doi.org/10.1021/jo952036t
Prinz, Helge, et al. "Syntheses of Anthracenones. 2. Preparation of 1,8-Dimethoxy- (Dimethylanthralin) and 4,5-Dihydroxy-9(10H)-anthracenone (Isoanthralin): A Revision." The Journal of organic chemistry vol. 61,8 (1996): 2857-2860. doi: https://doi.org/10.1021/jo952036t
Prinz H, Burgemeister T, Wiegrebe W, Müller K. Syntheses of Anthracenones. 2. Preparation of 1,8-Dimethoxy- (Dimethylanthralin) and 4,5-Dihydroxy-9(10H)-anthracenone (Isoanthralin): A Revision. J Org Chem. 1996 Apr 19;61(8):2857-2860. doi: 10.1021/jo952036t. PMID: 11667123.
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J Org Chem. 1996 Apr 19;61(8):2857-2860. doi: 10.1021/jo952036t.

Syntheses of Anthracenones. 2. Preparation of 1,8-Dimethoxy- (Dimethylanthralin) and 4,5-Dihydroxy-9(10H)-anthracenone (Isoanthralin): A Revision.

The Journal of organic chemistry

Helge Prinz, Thomas Burgemeister, Wolfgang Wiegrebe, Klaus Müller

Affiliations

  1. Institut für Pharmazie, Pharmazeutische Chemie I, and Zentrale Analytik, Universität Regensburg, D-93040 Regensburg, Germany.

PMID: 11667123 DOI: 10.1021/jo952036t

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 SnCl(2) 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 SnCl(2) in HCl and acetic acid leads to 1,8-dihydroxy-9(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.

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