一步法合成5,12-(二苯乙炔基)丁省化学发光染料

One-Step synthesis of 5,12-bis(phenylethynyl) naphthacene chemiluminescence dye

由邻苯二甲酸酐与萘作用生成2-α-萘羰基苯甲酸,产率63%。2-α-萘羰基苯甲酸在无水AlCl3,NaCl催化下脱水重排,得到5,12-丁省醌,产率68%。5,12-丁省醌与苯乙炔基锂在二氧六环,DMF中反应4h,水解后的混合物不经分离直接与氯化亚锡的盐酸溶液避光反应10h,一步法合成目标物,收率53%。

2-α-naphthoyl benzoic acid is obtained in 67% yield from reaction of phthalic anhydride with naphthalene. By the catalysis of a mixture of anhydrous AlC13 and NaCl, 5, 12-naphthacenequinone is synthesized through eyclodehydration and rearrangement of 2-α-naphthoyl benzoic acid. From which the title compotmd is synthesized in a one-step route. Thus, 5,12-naphthacenequinone reacts with lithium phenylethyayl in dioxan and DMF under 50℃ for 4h, the mixture formed is hydrolyzed, without further separation, then is treated with a solution of stannous chloride in hydrochloric acid for 10h to give the title compound with a yield of 53%.