Synthesis and Properties of Naphtha[1′,2′:5,6]pyrano [2,3-d]pyrimidin4(3H)-one Derivatives

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Abstract Seven new 2-substituted naphtha [1′,2′∶5,6] pyrano pyrimidin-4(3H)-one derivatives were synthesized by aza-Wittig reaction.First,2-aminonaphtha[1′,2′∶5,6]pyrano-3-carboxylate (Ⅰ) was obtained from 2-naphthol,ethyl cyanoacetate,aromatic aldehyde by Knoevenagl-Cope condensation reaction,then(Ⅰ) was reacted with triphenylphosphine to give iminophosphorane(Ⅱ).(Ⅱ) was reacted with phenyl isocyanate by aza-Wittig reaction to obtain the carbodiimides(Ⅲ),(Ⅲ) was reacted with amine, alcohol,phenol to give 2-substituted naphtha [1′,2′∶5,6] pyrano [2,3-d]pyrimidin-4(3H)-one Ⅳ(a-g).Their structures were determined by means of ~1H-NMR,MS and IR.The factors influencing the synthesis were discussed and the optimum reaction conditions were found out.The results indicated that reaction speed with mild steric hindrance of the nucleophilic reagent was faster,the efficiency was higher;the reaction time with electron-withdrawing group was shorter.

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Received 2009-09-15; published 2009-09-15

Cite this article:

YU Zhong-shan,LU Lian-ying,LI Xiu-zhen.Synthesis and Properties of Naphtha[1′,2′:5,6]pyrano [2,3-d]pyrimidin4(3H)-one Derivatives[J] Chemcial Industry and Engineering, 2009,V26(5): 395-399

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