An epoxide-opening cyclization/double Smiles rearrangement cascade approach to N-aryl-1,4-benzoxazines and N-arylindolines

Abstract

Reported herein is a transition-metal-free protocol for a regio- and diastereoselective synthesis of hydroxyalkyl-group embedded N-arylbenzo[b][1,4]oxazines and N-arylindolines based on an epoxide-opening cyclization/double Smiles rearrangement cascade of p-nosylamide-tethered epoxides. To...

Synthesis of benzimidazole-fused 1,4-benzoxazepines and benzosultams spiro-connected to a 2-oxindole core via a tandem epoxide-opening/SNAr approach

“…More elaborately, the S N Ar arylations of in situ generated epoxide-derived alkoxides have scarcely been reported. 11 Until 2010, this strategy was unknown, although a few step-wise epoxide-opening/S N Ar protocols have previously appeared in the literature. 12 In 2010, the Cleator and Hanson groups nearly simultaneously disclosed the first examples of intermolecular epoxide-opening/intramolecular S N Ar cascade reactions.…”