Aksenov Alexander V, Smirnov Alexander N, Aksenov Nicolai A, Bijieva Asiyat S, Aksenova Inna V, Rubin Michael
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation.
Org Biomol Chem. 2015 Apr 14;13(14):4289-95. doi: 10.1039/c5ob00131e. Epub 2015 Mar 11.
PPA-induced umpolung triggers efficient nucleophilic addition of unactivated anilines to nitroalkanes to produce N-hydroxyimidamides. The latter undergo sequential acid-promoted cyclocondensation with ortho-OH or ortho-NHR moieties to afford benzoxazoles and benzimidazoles, respectively.
PPA诱导的极性反转引发了未活化苯胺与硝基烷烃的高效亲核加成反应，生成N-羟基亚胺酰胺。后者分别与邻位羟基或邻位NHR基团进行连续的酸促进环缩合反应，分别得到苯并恶唑和苯并咪唑。
