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有机化学 ›› 2005, Vol. 25 ›› Issue (07): 830-834. 上一篇    下一篇

研究简报

氢化喹啉及其芳(杂)环稠合衍生物的合成

王进军*，谢磊，康明芹，张敏，李付国，崔丙存   

  1. (烟台大学应用化学系 烟台 264005 )
  • 收稿日期:2004-08-31 修回日期:2005-01-04 发布日期:2005-06-30
  • 通讯作者: 王进军

Synthesis of Hydrogenated Quinolines by Michael Addition of 1,3-Cyclohexanedione with β,β-Dicyanostyrene

WANG Jin-Jun*,XIE Lei,KANG Ming-Qin,ZHANG Min
LI Fu-Guo,CUI Bing-Cun   

  1. (Department of Applied Chemistry, Yantai University, Yantai 264005)
  • Received:2004-08-31 Revised:2005-01-04 Published:2005-06-30
  • Contact: WANG Jin-Jun

PDF

2336

被引次数

9

通过环己二酮与β-二腈基苯乙烯的Michael加成得到2-氨基-3-氰基-4-芳基-5-氧代-1,4,5,6,7,8-六氢喹啉(1); 4-苯基六氢喹啉(1a)与环己二酮发生胺的加成缩合反应生成2-N-(3-氧代-1-环己烯基)氨基-3-氰基-4-苯基-5-氧代-1,4,5,6,7,8-六氢喹啉(2), 在碱性和氯化亚铜催化下进一步环合成4-苯基-5-氨基-二-(2-氧代环己烷)并[b,g]-1,3-二氢萘啶(3). 芳醛、α-萘胺和环己二酮在乙醇中共回流, 则一锅法完成9-芳基-5,6,7,8,9,10-六氢苯并[c]吖啶酮(4)的合成. 对合成中所涉及的化学反应机理进行了尝试性的讨论. 新化合物1a～4c均经IR, 1H NMR 及元素分析证明其结构.

关键词: 环合反应, 含氮杂环化合物, 喹啉, 吖啶, 萘啶

2-Amino-3-cyano-4-aryl-5-oxo-1,4,5,6,7,8-hexahydroquinolines (1) were synthesized by Michael addition of 1,3-cyclohexanedione with β,β-dicyanostyrene. The condensation of 2-amino-3-cyano-4- phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline (1a) with 1,3-cyclohexanedione was carried out to give 2-(3-oxo-1-cyclohexenyl)amino-3-cyano-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline (2a) which was converted into 1,3-dihy-dro-4-phenyl-5-amino-bis(2-oxo-cyclohexano)[b,g]-1,8-naphthridine (3a). 5,6,7,8,9,10- Hexahydro-9-aryl-benzo[c]acridin-5-one (4) was obtained using one pot method by co-refluxing of aromatic aldehyde, α-naphthylamine and 1,3-cyclohexanedione. The mechanism of the related reactions was tentatively discussed and the structures of new compounds 1a～4c were characterized by elemental analysis, IR and 1H NMR spectra.

Key words: quinoline, naphthyridine, nitrogenated heterocyclic compound, acridine, cyclization reaction