9-Anthroxy. A protecting group removable by singlet oxygen oxidation

Abstract

7 2 Hz, allylic CH,), 4.95 (m, 2, ==CHz), and 5.7 ppm (m, 1, =CH).

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

“…Elucidation of the mechanism of how acid catalysis or base catalysis achieves this desirable selectivity has gained considerable interest. Barnett et al [18] investigated the p-toluenesulfonic acid catalyzed formation and dehydration of anthrone hemiacetals, found such reactions to occur incompletely, and went on to develop transetherification of 9-methoxyanthracene. The one-step dehydration procedure in method A becomes Scheme 2 feasible for the preparation of primary 9-alkoxy-1,5dichloroanthracenes when a large excess of a primary alcohol is used with sulfuric acid catalysis in benzene and the water byproduct is removed by azeotropic distillation [19].…”

“…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.…”

ChemInform Abstract: 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.…”

Synthesis of 9-Anthryl Ethers from trans-9,10-Dihydro-9,10-dimethoxy­anthracene by Acid-Catalyzed Transetherification

“…In case of primary alcohols, transetherification yields were 65-68%, which are much higher than previously reported (entries 2-6). 8,9,14 When 2-methoxyethanol was used, transetherification gave the corresponding 9-(2-methoxyethoxy)anthracene (2g) in good yield (73%, entry 7). On the other hand, when 1-bromoethanol was used, we obtained the desired product 2h in only 25% yield (entry 8).…”

“…However, reaction with allyl alcohol produced the desired product 2j, and this was stable enough to be isolated in a pure form at a yield of 57% (entry 10). The reaction was also performed using four diols (entries [11][12][13][14], to see whether intramolecular-annulated crown ether of anthracene at C9 and C10-position formed or not. However, when triethylene glycol was used (entry 14), only 9alkoxyanthracene (2n) was achieved as usual (65%).…”