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Access to 1,4-Dihydrobenzo[e][1,2,4]triazin-4-yl Derivatives
Christos P Constantinides1, Emilia Obijalska2, Piotr Kaszyński2,3
1Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, United States.
Abstract:
A simple, one-pot method for the preparation of 1-aryl-3-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals by addition of aryllithium to the readily available 3-phenylbenzo[e][1,2,4]triazine followed by aerial oxidation is described. The intermediate anion is also trapped as an N-benzyloxycarbonyl derivative and purified prior to deprotection and oxidation to the radical. The method was demonstrated for nine (het)arenes, and the regioselectivity of nucleophilic addition to the benzo[e][1,2,4]triazine and trapping of the intermediate anion with electrophiles was assessed computationally.