Chemical Research in Chinese Universities ›› 2009, Vol. 25 ›› Issue (6): 866-869.

• Articles • Previous Articles     Next Articles

Efficient Synthesis of 2-Substituted Quinolino[7', 8':5, 6]pyrano-[2, 3-d]pyrimidin-4(3H)-ones via Tandem Aza-Wittig Reaction

FANG Zheng-dong*, WANG Guo-hong and WANG Dun-jia   

  1. College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, P. R. China
  • Received:2009-10-30 Revised:2009-02-23 Online:2009-11-25 Published:2010-01-25
  • Contact: FANG Zheng-dong. E-mail: zdfang08@yahoo.com.cn
  • Supported by:

    Supported by the Mid-young Scholar’s Science and Technology Program of the Education Department of Hubei Province, China(No.Q20082202).

Abstract:

An efficient method is described for the synthesis of 2-substituted quinolino[7',8':5,6]pyrano[2,3-d] pyrimidin-4(3H)-ones(6) via a tandem aza-Wittig annulation process. The iminophosphorane(3) reacted with aromatic isocyanates, followed by heterocyclization on the addition of secondary amines, phenols or alcohols to give the corresponding guanidine intermediates(5), which were cyclized in the presence of a catalytic amount of a base to tetracyclic compounds 6 in good yields. The corresponding carbodiimide(4) and guanidine-type intermediate compounds 5 need not be isolated.

Key words: Quinolinopyran; Pyranopyrimidin-4(3H)-one; Aza-Wittig reaction