Huang Xian, Liu Zhanxiang
Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou 310028, Zhejiang, P. R. China.
J Org Chem. 2002 Sep 20;67(19):6731-7. doi: 10.1021/jo020175m.
An efficient method for the preparation of polymer-bound cyclic malonic acid ester starting from Merrifield resin has been developed. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent double substitution with nucleophilic reagents, such as arylamine, urea, thiourea, 2-aminobenzothiazoles, or isothiosemicarbazones, afforded the corresponding polymer-bound substituted aminomethylene cyclic malonic acid esters, which upon thermal treament led to 4(1H)-quinolones, 3-substituted uracils and thiouracils, 4H-pyrimido[2,1-b]benzothiazol-4-ones, and 1-(N-alkylidene or benzylideneamino)-1,6-dihydro-2-methylthio-6-oxo-pyrimidines, depending on the structures of the nucleophilic reagents.
已开发出一种从 Merrifield 树脂开始制备聚合物负载环状丙二酸酯的有效方法。树脂负载的环状丙二酸酯与原甲酸三乙酯反应，随后用亲核试剂如芳胺、尿素、硫脲、2-氨基苯并噻唑或异硫脲半卡巴腙进行双取代，得到相应的聚合物负载取代氨基亚甲基环状丙二酸酯，根据亲核试剂的结构，经热处理后可得到 4(1H)-喹诺酮、3-取代尿嘧啶和硫代尿嘧啶、4H-嘧啶并[2,1-b]苯并噻唑-4-酮以及 1-(N-亚烷基或亚苄基氨基)-1,6-二氢-2-甲硫基-6-氧代嘧啶。
