5H-茚并[1,2-b]吡啶的某些5-取代衍生物的合成

Syntheses of Some 5-Substituted Derivatives of 5H-Indeno[1.2-b] Pyridine

报告了文题化合物的合成方法。实验结果表明,5-溴-5H-茚并[1,2-b]吡啶(Ⅱ)的溴原子比较活泼,可被多种亲核试剂所取代。溴代物与含活泼亚甲基的丙二酸二乙酯反应,溴被(二乙氧羰基-)甲基取代,经水解,生成5-(二羧基-甲基)-5H-茚并[1,2-b]吡啶(Ⅳ),再经脱羧,即转化成5-羧甲基-5H-茚并(1,2-b)吡啶(Ⅴ)。溴代物与饱和环状仲胺哌啶反应,溴被哌啶子基取代,生成5-哌啶子基-5H茚并(1,2-b)吡啶(Ⅶ)。溴代物与芳胺类化合物邻-氨基苯甲酸酯反应,溴被N-芳胺基取代,生成5-(邻-烷氧羰基苯胺基)-5H-茚并[1,2-b]吡啶(Ⅷ)和5-(邻-烷氧羰基苯亚胺基)-5H-茚并[1,2-b]吡啶(IX)。所得各种反应产物,均经波谱分析得以证实。

Some 5-substituted derivatives of 5H-indeno [1,2-b] pyridine (Ⅰ) have been synthesized by bromination of compound I and consequent nucleophilic substitution of 5-Br-5H-indeno [1,2-b] pyridine (Ⅱ). Experimental results show that the bromine atom of compound Ⅱ is relatively reactive and can be substituted by nucleophile. The bromocompound Ⅱ reacts with diethyl malonate to form 5-(diethoxycarbonylmethyl)-5H-indeno [1,2-b] pyridine (Ⅲ) with saturated cyclic secondary amine piperidine to form 5-(piperidino)-5H-indeno [1,2-b] pyridine (Ⅶ) and with aromatic amine o-aminobenzoate to form 5-(o-alkoxycarbonyanilino)-5H-indeno [1,2-b] pyridine (Ⅷ) and 5-(o-alkoxycarbonyJphenylimido)-5H-indeno [1,2-b] pyridine (Ⅸ). The structures of all the products so synthesized have been identified by spectrographic analysis.