Ghorai Manas K, Sahoo Ashis Kumar, Bhattacharyya Aditya
Department of Chemistry, Indian Institute of Technology , Kanpur, Uttar Pradesh 208016, India.
J Org Chem. 2014 Jul 18;79(14):6468-79. doi: 10.1021/jo500888j. Epub 2014 Jul 1.
A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hitherto unprecedented cascade cyclization reaction sequence comprising a Cu-catalyzed cross dehydrogenation C-N coupling and an Ullmann C-C bond formation reaction. The tetrahydrobenzoxazepine and the tetrahydrobenzothiazepine derivatives have also been synthesized via the ring-opening of aziridines with 2-bromobenzyl alcohols and -mercaptan, respectively, followed by Cu-catalyzed N-arylation reaction.
一种简单且意想不到的合成外消旋和非外消旋四氢二苯并咪唑并氮杂卓的途径是偶然发现的，该途径通过N-活化氮丙啶与2-溴苄胺的S(N)2型开环反应，随后是一个前所未有的级联环化反应序列，包括铜催化的交叉脱氢C-N偶联和乌尔曼C-C键形成反应。四氢苯并恶唑嗪和四氢苯并噻嗪衍生物也分别通过氮丙啶与2-溴苄醇和硫醇的开环反应，随后进行铜催化的N-芳基化反应合成。
