萘并吡喃并[2,3-d]嘧啶-4(3H)-酮衍生物的合成与表征

摘要通过氮杂Wittig反应合成了7种萘并吡喃并[2,3-d]嘧啶-4(3H)-酮衍生物。首先用2-萘酚、氰乙酸乙酯和芳醛通过Knoevenagl-Cope缩合得到2-氨基萘并吡喃(Ⅰ),(Ⅰ)再与三苯基膦反应得到膦亚胺中间体(Ⅱ)。(Ⅱ)与芳基异氰酸酯采用aza-Wittig反应得到碳二亚胺(Ⅲ)。(Ⅲ)再分别与胺、醇、酚反应合成了萘并吡喃并[2,3-d]嘧啶-4(3H)-酮Ⅳ(a-g)。目标化合物结构经1H-NMR、MS和IR进行了表征。试验考察了亲核试剂及反应条件对产品收率的影响。结果表明,亲核试剂空间位阻小反应速度较快,收率高;若有吸电子基团时,反应时间缩短。

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	余中山
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关键词：萘并吡喃并[2 3-d]嘧啶-4(3H)-酮膦亚胺 aza-Wittig反应亲核试剂合成

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

引用本文:

余中山;卢莲英;李秀珍;.萘并吡喃并[2,3-d]嘧啶-4(3H)-酮衍生物的合成与表征[J]. 化学工业与工程, 2009,26(5): 395-399

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, 2009,26(5): 395-399

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