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以2-氨基-4-三氟甲基-5-甲基-噻吩-3-羧酸乙酯(1)为起始原料制得膦亚胺2.在碳酸钾的催化下,膦亚胺2与芳基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上2,2’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]3;膦亚胺2与烷基异氰酸酯和伯二胺的氮杂Wittig反应制得嘧啶环上3,3’取代的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]4.化合物3的核磁共振氢谱表明关环反应在嘧啶环的2,2’位;化合物4的核磁共振氢谱表明关环反应在嘧啶环的3,3’位.对合成反应机理的推导及目标产物核磁共振氢谱数据的分析解释了此合成反应的选择性.
The phosphinimine 2 was obtained starting from ethyl 2-amino-4-trifluoromethyl-5-methyl-thiophene-3-carboxylate (1) 2,2’-substituted bis [thieno [2,3-d] pyrimidin-4 (3H) -one] 3 on the pyrimidine ring; Phosphinimine 2 Aza-3-substituted bis [thieno [2,3-d] pyrimidin-4 (3H) -one] pyrimidine ring was synthesized by aza-Wittig reaction of alkyl isocyanate and primary diamine. Resonance hydrogenation showed that the ring-closing reaction was at the 2,2 ’position of the pyrimidine ring, and the 1H NMR spectrum of the compound 4 showed that the ring-closing reaction was at the 3,3’ position of the pyrimidine ring. The derivation of the synthesis reaction mechanism and the target product NMR Analysis of the spectral data explains the selectivity of this synthesis reaction.