Syntheses of Anthracenones. 1. Sodium Dithionite Reduction of peri-Substituted Anthracenediones

Abstract

The reaction of peri-substituted anthracenediones with sodium dithionite in dimethylformamide and water has been investigated. The system selectively reduces the carbonyl group flanked by the peri substituents of the anthracenediones to give the corresponding 4,5-disubstituted 9(10H)-anthracenones and thus provides a route to anthracenones which are otherwise difficult to obtain. Many functional groups can be tolerated, the reaction is compatible with the presence of peri alkoxy groups and unsaturated side chains of the starting anthracenediones, and the reduction does not go beyond the anthracenone stage. However, the formation of anthracenones depends on the nature of the peri substituents. No products were obtained from the 1,8-dimethyl-substituted anthracenedione and the parent compound with no substituents.

The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes

“…4,5-Dichloro-9-anthrone was prepared by a published procedure. [30] 1,8-Dichloro-10-cyclohexylanthracene (1), 10-benzyl-1,8-dichloroanthracene (2), 10-tert-butyl-1,8-dichloroanthracene (3), 1,8-dichloro-10-methylanthracene (4) and 1,8-dichloro-10-isopropylanthracene (6) were synthesized by a modified procedure of Toyota et al [31] 10-Butyl-1,8-dichloroanthracene (7) and 1,8-dichloro-10-phenylanthracene (8) were also synthesized by a modified procedure of Toyota et al [32] All triptycenes were synthesised by the method described by Rogers and Averill [15] with a variation in work-up depending on the substituents. The reactions were carried out by using freshly distilled and dry solvents from solvent stills.…”

Synthesis and Cytotoxicity of 9-Alkoxy-1, 5-dichloroanthracene Derivatives in Murine and Human Cultured Tumor Cells

“…lating agents [14][15][16][17][18][19]. Nevertheless, with an alkoxy moiety attached to the anthracene pharmacophore at C-9, it is believed that compounds having biological activity could be obtained.…”

Cornified Envelope Formation by Anthralin, Simple Analogues, and Related Anthracenones

“…Anthralin [36] , anthralin dimer [36] and anthralin triacetate [37] were prepared as described, and the required anthracenone analogues were available from previous work: 6 [38] , 8-11 [39] , 12 [40] , 13 [20] , 14 [41] , 15-17 [42] .…”