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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (17): 2070-2074. 上一篇    

研究简报

吡啶高三蝶烯的合成

张红1,2，刘文杰1，曹德榕*,1，江焕峰1   

  1. (1华南理工大学化学化工学院 广州 510640)
    (2广东药学院医药化工学院 广州 510006)
  • 投稿日期:2011-02-17 修回日期:2011-04-12 发布日期:2011-05-08
  • 通讯作者: 曹德榕 E-mail:drcao@scut.edu.cn
  • 基金资助:

    国家自然科学基金

Synthesis of Pyridinylhomotriptycene

Zhang Hong1,2 Liu Wenjie1 Cao Derong*,1 Jiang Huanfeng1   

  1. (1 School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640)
    (2 School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Guangzhou 510006)
  • Received:2011-02-17 Revised:2011-04-12 Published:2011-05-08
  • Contact: Derong Cao E-mail:drcao@scut.edu.cn

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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).

关键词: 高三蝶烯, 吡啶高三蝶烯, 10,10-二(2-甲氧基-4-吡啶甲基)-9(10H)蒽酮, 蒽醇, 1,7-亲电脱水反应

2-Bromo-4-methylpyridine (1) was converted to 2-bromo-4-iodomethylpyridine (3) by chlorination 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.

Key words: homotriptycene, pyridinylhomotriptycene, 10,10-bis(2-methoxypyridin-4-yl-methyl)-9(10H)- anthrone, anthracenol, 1,7-electrophilic dehydration