不对称树枝状咔唑类衍生物的合成

摘要

Three kinds of novel dendritic carbazole derivatives were designed and synthesized via three steps using 1,8-diiodobiphenyl and 1,4-dibromobenzene as starting material.In this process,two pairs of conjugate molecules,which were obtained through Ullmann coupling reaction between phenyldihalide and carbazole,reacted with NBS to generate three multi-brominated intermediates:3,3′,6-tribromo-1, 4-bis-carbazolyl-benzene,3,3′,6,6′-tetrabromo-1,4-bis-carbazolyl-benzene,3,3′,6- tribromo-1,4-bis-carbazolyl-biphenyl.Then,the desired novel dendritic carbazole derivatives including 3,3′,6-Tri(N-car-bazolyl)-1,4-bis-carbazolyl-benzene,3,3′,6,6′-Tetra (N-carbaolyl)-1,4-bis-carbazolybenzene,3,3′,6-Tri(N-carbazolyl)-1,8-bis-carbazolyl-biphenyl were formed through Ullmann coupling again with multi-brominated compounds and carbazole.The intermediates and target products were characterized by 1 H NMR,13 C NMR and MS.%以1，4-二溴苯和1，8-二碘联苯为原料分别与咔唑发生乌尔曼偶联反应制得两种相应的成对偶联分子，用 NBS 作为溴化试剂与这两种分子反应制得新型的多溴代产物：3，3′，6-三溴-1，4-双咔唑基苯、3，3′，6，6′-四溴-1，4-双咔唑基苯和3，3′，6-三溴-1，8-双咔唑基联苯。该溴化物与咔唑在铜催化下发生乌尔曼偶联反应制得3种新颖的树枝状咔唑类衍生物：3，3′，6-三（N-咔唑基）-1，4-双咔唑基苯、3，3′，6，6’-四（N-咔唑基）-1，4-双咔唑基苯、3，3′，6-三（N-咔唑基）-1，8-双咔唑基联苯。通过核磁、质谱分别对所合成的化合物进行了表征。