纳米二氧化钛催化二苯并1,10-菲咯啉衍生物的合成研究

摘要

Nine dibeno[b,j]-1,10-phenanthroline derivatives(3a～3i, 3b, 3c, 3e～3g, 3i were new compounds) were firstly synthesized by the tandem-Friedlander reaction of 1,2-cyclohexanedione with 2-amino benzoyl derivatives using nano-TiO2 as catalyst . The structures were characterized by 1H NMR, 13C NMR, and HR-MS(ESI).The optimum reaction conditions for the model synthesis of 5,8-diphenyl-6,7-dihydrodibenzo[b,j][1,10]phenanthroline(3a) were obtained as follows:the mole ratio of 1a and 2 was 2.1 :1, anatase titanium dioxide dosage was 0.2 eq., reaction at 80 ℃for 7 h in acetonitrile.The yield of 3a is up to 83％.Moreover, the reaction mechanism was also discussed .%首次报道了纳米TiO2催化1,2-环己二酮与2-氨基苯甲酰衍生物的串联Friedlander反应,合成了9个二苯并1,10-菲咯啉的衍生物(3a～3i),其中3b,3c,3e～3g和3i为新化合物,其结构经1 H NMR,13 C NMR和HR-MS(ESI)表征.以6,7-二氢-5,8-二苯基苯并[1,10]菲咯啉(3a)的合成为例,对反应条件进行了优化.最佳反应条件为:锐钛型纳米二氧化钛用量为0.2 eq.,1a与2投料比为2.1:1,乙腈为溶剂,于80℃反应7 h,收率83％.并对反应机理进行了探讨.