Synthesis and isolation of iodocarbazoles. Direct iodination of carbazoles by<i>N</i>-iodosuccinimide and<i>N</i>-iodosuccinimide-silica gel system
作者:Sergio M. Bonesi、Rosa Erra-Balsells
DOI:10.1002/jhet.5570380111
日期:2001.1
iodination reaction of different carbazole derivatives such as 2-acetoxycarbazole (2), 3-bromocarbazole (3) and 3-nitrocarbazole (4) was also studied and the corresponding iododerivatives, 2a, 2b, 2c, 3a, 3b, 4a and 4b, are described for the first time. Semiempirical PM3 calculations have been performed in order to predict reactivity of carbazole (1), substituted carbazoles (2-4) and iodocarbazoles (1a-1e
咔唑(1)用各种碘化试剂进行亲电子芳香取代。尽管通过咔唑碘化制得的3-碘咔唑(1b)和3,6-二碘咔唑(1d)已经过分离和表征,但是1-碘咔唑(1a),1,6-二碘咔唑(1c)和1,3,6从未从反应混合物中分离出-三碘咔唑(1e)。报告了1a,1b,1c,1d和1e的制备,后续分离和表征(mp,t r,R f,1 H-nmr,13 C-nmr和ms)。作为碘化试剂,NaIO4 / I 2和的NaIO 4(i)中的乙醇用掺杂催化硫酸的量和(ii)中的乙酸,和/ KI的混合物Ñ -odosuccinimide和Ñ碘代丁二酰亚胺硅胶在二氯甲烷和氯仿中已经使用和比较了它们的用途。不同的咔唑衍生物,如2- acetoxycarbazole(的碘化反应2),3-溴代咔唑(3)和3- nitrocarbazole(4)也进行了研究和相应iododerivatives,2A,2B,2C,3A,3B,4A和