Dihydrobenzoxazines and tetrahydroquinoxalines by a tandem reduction??reductive amination reaction

RA Bunce, DM Herron, LY Hale

Index: Bunce, Richard A.; Herron, Derrick M.; Hale, Lu Y. Journal of Heterocyclic Chemistry, 2003 , vol. 40, # 6 p. 1031 - 1039

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Citation Number: 36

Abstract

Abstract A tandem reduction-reductive amination reaction has been applied to the synthesis of 3, 4-dihydro-2H-1, 4-benzoxazines and 1-acetyl-1, 2, 3, 4-tetrahydroquinoxalines. The nitroketones required for the benzoxazine ring closures were prepared by (A) alkylation of the anion derived from 2-nitrophenol with an allylic halide or (B) nucleophilic aromatic substitution of an allylic alkoxide on 2-fluoro-1-nitrobenzene followed by ozonolysis. ...