Iron-Mediated Bromocyclization of Olefinic Amides for the Synthesis of Bromobenzoxazines
Tong‐Tong Zhao, Qiang Bian, Da‐Zhen Xu, Wei‐Guang Zhao, Yuwei Zhao, Linlin Xu
Abstract
Abstract An iron-mediated bromination/cyclization for the synthesis of bromobenzoxazines from olefinic amides has been successfully developed. In this protocol, the simple iron salt FeBr3 was employed as a bromination reagent, giving the bromobenzoxazine products in moderate to excellent yields. This methodology features good functional group tolerance, gram-scale synthesis, and green reaction conditions by the use of air as the terminal oxidant. Preliminary mechanistic studies suggest that a free radical pathway is involved.
Topics & Concepts
ChemistryHalogenationReagentFunctional groupOrganic chemistryReaction conditionsCombinatorial chemistryCatalysisPolymerVanadium and Halogenation ChemistryPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Biological Evaluation