Departament de Química Inorgànica i Orgànica, Universitat Jaume I , Castelló 12071, Spain.
Faculty of Chemistry, Kharazmi University , Tehran 15719-14911, Iran.
J Org Chem. 2018 Feb 2;83(3):1252-1258. doi: 10.1021/acs.joc.7b02795. Epub 2018 Jan 22.
Nitroepoxides are easily transformed into benzodiazepines, tetrahydrobenzodiazepines, imidazopyridines, and N-alkyl tetrahydroquinoxalines by treatment with 2-aminobenzylamines, 2-aminopyridines, and N-alkyl 1,2-diaminobenzenes, respectively. Regioselectivity is controlled through attack of the most nucleophilic nitrogen of the unsymmetrical diamine to the β position of the epoxide. These reactions represent an efficient way to prepare privileged bioactive structures.
硝基亚胺很容易通过与 2-氨基苄基胺、2-氨基吡啶和 N-烷基 1,2-二氨基苯分别反应转化为苯并二氮杂卓、四氢苯并二氮杂卓、咪唑并吡啶和 N-烷基四氢喹喔啉。通过非对称二胺中最具亲核性的氮原子进攻环氧化物的β位来控制区域选择性。这些反应代表了一种制备优势生物活性结构的有效方法。
