Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (07): 830-834. Previous Articles     Next Articles

Reports

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

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