10,10-二吡啶甲基-9,10-二氢蒽的合成研究

Synthesis of 10,10-Bispyridinylmethyl-9,10-dihydroanthracenes

蒽酮1和氯甲基吡啶盐酸盐2在甲苯中回流反应生成10,10-二吡啶甲基-9(10H)蒽酮(3),收率63%～68%;3用硼氢化钠还原生成10,10-二吡啶甲基-9,10-二氢蒽-9-醇(4),收率87%～90%;蒽醇4在酸催化下发生歧化反应,得到还原产物10,10-二吡啶甲基-9,10-二氢蒽(5)和氧化产物蒽酮3.该歧化反应受催化剂、溶剂和反应温度等影响.当蒽醇4用三氟化硼为催化剂、甲苯为溶剂、回流反应,5的收率达到74%.所合成的新化合物都经1H NMR,13C NMR,MS和元素分析表征确认.

Anthrone 1 and picolyl chloride hydrochloride 2 reacted in refluxing toluene for 2 h to give 10,10-bispyridinylmethyl-9（10H）-anthrones（3） in 63%～68% yields.Reduction of 3 with NaBH4 at 80 ℃ afforded 10,10-bispyridinylmethyl-9,10-dihydroanthracen-9-ols（4） in 87%～90% yields.The dispropor-tionation reaction of 4 with acid as catalyst gave the reduced product,10,10-bispyridinylmethyl-9,10-dihy-droan-thracenes（5） and the oxidized product,anthrones 3.The disproportionation reaction was influenced by catalyst,solvent and reaction temperature.When 4 was catalyzed by BF3 in refluxing toluene,the highest yield of 5 was up to 74%.The structures of all new compounds were confirmed by 1H NMR,13C NMR,MS techniques and elemental analysis.