吡啶高三蝶烯的合成

Synthesis of Pyridinylhomotriptycene

2-溴-4-甲基吡啶(1)经氯代和碘代反应合成了2-溴-4-碘甲基吡啶(3),3和蒽酮(4)反应生成10,10-二(2-溴-4-吡啶甲基)-9(10H)蒽酮(5),5在3 MPa下与NaOCH3反应得到10,10-二(2-甲氧基-4-吡啶甲基)-9(10H)蒽酮(6),6经硼氢化钠还原得到蒽醇(7),7在对甲苯磺酸催化下发生分子内的1,7-亲电脱水反应,生成吡啶高三蝶烯(8).

2-Bromo-4-methylpyridine（1） was converted to 2-bromo-4-iodomethylpyridine（3） by chlorina-tion and iodination;3 reacted with anthrone（4） to form 10,10-bis（2-bromopyridin-4-yl-methyl）-9（10H）anthrone（5）.Methoxy group was introduced to pyridine ring by nucleophilic substitution at 3 MPa with NaOCH3 to give 10,10-bis（2-methoxypyridin-4-yl-methyl）-9（10H）-anthrone（6）.6 was reduced by NaBH4 to give anthracenol（7）.7 was catalyzed by p-TsOH to give pyridinylhomotriptycene（8） by an intramolecular 1,7-electrophilic dehydration.