N-甲基四氢咔唑类化合物的合成研究

Synthesis of N-methyltetrahydrocarbazoles

以不同取代的苯肼盐酸盐和不同取代的环己酮为原料,通过三聚氯氰催化的四氢咔唑合成和N甲基保护两步反应,在温和的、环境友好的条件下,高效地合成了6个N-甲基四氢咔唑化合物,产率为70%~88%。并以4-甲基苯肼盐酸盐和环己酮为模型底物,对Fischer吲哚合成法进行优化,建立了以溶剂为乙醇,温度为80℃,三聚氯氰0.5当量,反应时间为2 h为最佳反应条件。目标产物经氢谱1H NMR鉴定。

A concise preparation of tetrahydrocarbazole derivativeswas described in 70% - 80% overall yields starting from various phenyl hydrazines and different cyclohexanones via 2,4,6-trichloro-1,3,5-triazine（TCT）mediated Fischer indole synthesis and protection of nitrogen atom. Taking 4-methyl phenyl hydrazine hydrochloride and cyclohexanone as the model substrates to survey the reaction parameters,it was found that the use of 0. 5 equivalent of TCT in ethanol under 80 ℃ for 2 h was chosen as the standard reaction conditions. The structures of target products were identified by1 H NMR.