7-endo cyclization of 2,3-epoxyamides and 2,3-aziridine carboxamides by intramolecular Friedel-Crafts reaction

A high yielding regio- and diastereoselective 7-endo 2,3-epoxyamides and 2,3-aziridine carboxamide cyclization is reported. Several aryl and alkyl trans-2,3-epoxyamides were reacted with BF3 center dot OEt2 to afford the corresponding 4-hydroxy-5-alkyl/aryl-tetrahydro-2-benzazepin-3-ones. In addition, arene cyclization with aryl 2,3-aziridine carboxamides was investigated. (C) 2014 Elsevier Ltd. All rights reserved.