Chemical Research in Chinese Universities ›› 2009, Vol. 25 ›› Issue (5): 657-661.

• Articles • Previous Articles     Next Articles

Efficient Synthesis of Dicycloalkenopyridines: One-pot Multicomponent Condensation of Aldehydes with Cyclic Ketones

CAI Xi-mei, WANG Qi-fang and YAN Chao-guo*   

  1. College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. China
  • Received:2008-08-04 Revised:2008-09-11 Online:2009-09-25 Published:2009-12-07
  • Contact: YAN Chao-guo. E-mail: cgyan@yzu.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(No. 20672091).

Abstract:

Under microwave irradiation, the one-pot multicomponent condensation reaction of three moles of aromatic aldehydes with two moles of cyclic ketones having free α,α'-methylene positions such as cyclopentanone or cyclohexanone in the presence of ammonium acetate and acetic acid afforded dicycloalkenopyridines with two α-arylidene groups in high yields. Under the similar reaction condition, the reaction of aromatic aldehydes with 1-tetralone having only one α-methylene position alternatively resulted in 10-aryl-2,3:5,6-dibenzoacridines.

Key words: Pyridine; Acridine; Microwave irradiation; Aromatic aldehyde; Cyclic ketone; Aldol condensation