Oxidative Synthesis of Benzo[1,4]oxazines from α-Branched Primary Amines and Ortho-Benzoquinones


The efficient oxidative construction of benzo[1,4]oxazines from simple α-branched amines and ortho-benzoquinones is reported. The procedure pivots on a triethylamine and iodine mediated oxidative ring closure from the ketimine intermediate formed upon their condensation. This reaction was shown to tolerate a variety of α-branched benzylamines and downstream derivatization to substituted benzomorpholine structures was also demonstrated.


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