3-烷基-5-苯基亚甲基-2-硫代-4-咪唑啉二酮类化合物的合成

Synthesis of 3-alkyl-5-phenylmethylidene-2-thio-4-imidazo- lidinones

氯乙酸乙酯和叠氮化钠的亲核取代反应产物α-叠氮基乙酸乙酯与苯甲醛缩合得到α-叠氮基苯基亚甲基乙酸乙酯,此缩合产物与三苯基膦的Staudinger反应制得的α-乙酯基苯基亚甲基膦亚胺,再与烷基异氰酸酯、硫化钠/冰醋酸发生三组分串联aza-Wittig反应,合成出标题化合物。探讨了反应进行的条件和产物的波谱性质,提出了可能的环化反应机理。生成的环化产物均为新的化合物,其结构经元素分析、IR、1HNMR和MS确证。

α-Azidoacetic ester, obtained from nucleophilic substitution reaction of chloroacetic ester and sodium az-ide,and benzaldehyde were condensed into α-azidophenyl-methylideneacetic ester. α-Ethoxycarbonylphenylmethyli-deneiminophosphoranes, prepared from Staudinger reaction of α-azidophenylmethylideneacetic ester and tripheny-Iphosphine,reacted with alkyl isocyanate and Na2S/HOAc via aza-Wittig reactions in series with three components to give 3-alkyl-5-phenylmethylidene-2-thio-4-imidazolidino-nes. The reaction condition and the spectral properties of cyclized compounds were researched and a possible mechanism for the cyclization reaction was put forward. All the cyclized products are new, and their structures were confirmed by elemental analysis, IR, HNMR and MS.