An epoxide-opening cyclization/double Smiles rearrangement cascade approach to N -aryl-1,4-benzoxazines and N -arylindolines.
Organic & biomolecular chemistry(2023)
Abstract
Reported herein is a transition-metal-free protocol for a regio- and diastereoselective synthesis of hydroxyalkyl group-embedded -arylbenzo[][1,4]oxazines and -arylindolines based on an epoxide-opening cyclization/double Smiles rearrangement cascade of -nosylamide-tethered epoxides. To the best of our knowledge, this is the first report of the integration of epoxide-opening cyclization with Smiles rearrangement in a cascade fashion, enabling simultaneous construction and -arylation of N-heterocycles. The reaction employs substrates derived from commercially available 2-nitrophenols and easily accessible allylic halides/alcohols, and exhibits a broad substrate scope and delivers the products in high yields.
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Key words
rearrangement cascade approach,cyclization/double,epoxide-opening,n-arylindolines
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