摘要
应用胂叶立德合成吲哚,四嗪,异(口恶)唑已有文献报道,而呋喃环衍生物用胂叶立德合成的方法,尚未见报道.参考Takei等用硫叶立德合成呋喃衍生物的方法,用一系列稳定的胂叶立德分别与双烯酮反应,获得了相应的产物,提供了一种方便地合成3-羟基映喃衍生物的方法.其反应式如下:产物经元素分析,IR和HNMR鉴定,除3c和3d外,均为新化合物.从HNMR数据分析,除3f外,羟基质子的信号均在δ9.77ppm以上的低场出现.在红外光谱图中,羰基的伸缩振动也在低频率1610cm附近出现吸收.这表明呋喃环上羟基的氢质子与羰基氧生成了分子内氢键.Hamlet报道,稳定的胂叶立德能与烯酮顺利进行Wittig反应,失去氧化三苯胂,生成丙二烯衍生物.我们用苯甲酰基亚甲基三苯胂与双烯酮反应,反应物经薄板层析分离,未得到三苯胂,而分离出氧化三苯胂.胂叶立德与双烯酮反应,失去三苯胂,生成呋喃衍生物,类似硫叶立德的性质.
This paper reports a convenient method for the synthesis of 3-hydroxyfuran derivatives,by the reaction of ketene dimer(2)with stabilized arsonium ylides(la~f).A typical run was as follows:ketene dimer was added to a dry benzene solution ofα-thenoylmethylenetriphenylarsorane(la)at room temperature under nitrogen atmosphere and the solution was refiuxed for three hours.After removal of the solvent,the precipitate was purified by silica gel column chromatography to afford 2-(α-thenoyl)-3-hydroxy-5-methylfuran(3a).Similarly,2-(α-furoyl)-,2-benzoyl-,2-(p-chlorobenzoyl)-,2-(p-bromobenzoyl)-and 2-(p-nitrobenzoyl)-3-hydroxy-5-methylfurans were synthesized by the reactions of the arsonium ylides(lb~f)with ketene dimer in high yields.The structures of all products have been ascertained by elemental analyses,IR and~1H NMR spectroscopy.
出处
《化学学报》
SCIE
CAS
1985年第4期403-405,共3页
Acta Chimica Sinica
