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Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols
Synlett ( IF 1.7 ) Pub Date : 2018-10-02 , DOI: 10.1055/s-0037-1610995
Maki Minakawa 1 , Kouichi Watanabe 2 , Satoru Toyoda 1 , Yasuhiro Uozumi 3
Affiliation  

We developed an environmentally friendly iridium-catalyzed direct cyclization of aromatic amines with diols that generates the corresponding N-heterocyclic compounds with water as the sole by-product. Thus, under conditions of 165 °C for 18 hours, the direct cyclization of N-methylanilines with 1,3-propanediol by using an IrCl3 catalyst with rac-BINAP as a ligand in mesitylene afforded the corresponding tetrahydroquinoline derivatives with yields ranging from 73 to 83%. ­Under similar reaction conditions, direct cyclization of anilines with 1,3-propanediol produced the corresponding tetrahydrobenzoquinolizine derivatives with yields ranging from 26 to 76%.

中文翻译:

芳香胺与二醇的铱催化直接环化

我们开发了一种环保的铱催化芳香胺与二醇直接环化,生成相应的 N-杂环化合物,水作为唯一的副产物。因此,在 165 °C 18 小时的条件下,使用 IrCl3 催化剂与 rac-BINAP 作为均三甲苯中的配体,N-甲基苯胺与 1,3-丙二醇直接环化得到相应的四氢喹啉衍生物,产率范围为 73 至83%。在类似的反应条件下,苯胺与 1,3-丙二醇直接环化产生相应的四氢苯并喹嗪衍生物,产率范围为 26% 至 76%。
更新日期:2018-10-02
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