2-氨基-4-(4-氟苯基)-4?6-二氢氧杂环戊烷[4,3,2-CD]-3-甲腈的合成研究

Study of 2-amino-4-(4-fluorphenyl)-4?6-dihydrooxepino [4,3,2-cd] indole-3-carbonitrile synthesis

以丙二腈、对氟苯甲醛、4-羟基吲哚为原料,三乙烯二胺为催化剂合成了3?4-稠合三环吲哚类化合物2-氨基-4-(4-氟苯基)-4?6-二氢氧杂环戊烷[4?3?2-CD]-3-甲腈。通过单因素对比实验,确定的最佳反应条件为:原料4-羟基吲哚、丙二腈和对氟苯甲醛的物质的量比为1∶1∶1?4-羟基吲哚与三乙烯二胺的物质的量比为1∶0.6,溶剂无水乙醇的用量为2mL,反应时间6h,反应温度60℃。在此最佳反应条件下,2-氨基-4-(4-氟苯基)-4?6-二氢氧杂环戊烷[4?3?2-CD]-3-甲腈的收率达到93%(以4-羟基吲哚计)。用NMR对合成的产品进行了表征,并初步探讨了反应机理。

The 3?4-fused tricyclic anthracene 2-amino-4-(4-fluorphenyl)-4?6-dihydrooxepino[4?3?2-cd]indole-3-carbonitrile was synthesized using malononitrile,p-fluorobenzaldehyde and 4-hydroxyindole as raw materials and triethylenediamine as catalyst.The optimal reaction conditions were determined by single factor comparison experiments:1 mmol 4-hydroxyindole,1 mmol malononitrile,1 mmol p-fluorobenzaldehyde as raw material,0.6 mmol triethylenediamine as catalyst,2 mL absolute ethanol was used as a solvent,the reaction time was 6 h,and the reaction temperature was 60℃.Under the optimal reaction conditions described above,2-amino-4-(4-fluorphenyl)-4?6-dihydrooxepino[4?3?2-cd]indole-3-carbonitrile was obtained with the yield of 93%(based).The synthesized product was characterized by NMR and the reaction mechanism was preliminarily discussed.