A general strategy for the synthesis of cyclic N-aryl hydroxamic acids via partial nitro group reduction

…, BM Bechle, AB Dounay, E Evrard, X Gan…

Index: McAllister, Laura A.; Bechle, Bruce M.; Dounay, Amy B.; Evrard, Edelweiss; Gan, Xinmin; Ghosh, Somraj; Kim, Ji-Young; Parikh, Vinod D.; Tuttle, Jamison B.; Verhoest, Patrick R. Journal of Organic Chemistry, 2011 , vol. 76, # 9 p. 3484 - 3497

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Citation Number: 12

Abstract

We describe a generalized approach to stereocontrolled synthesis of substituted cyclic hydroxamic acids (3-amino-1-hydroxy-3, 4-dihydroquinolinones) by selective reduction of substituted 2-nitrophenylalanine substrates. Compounds in this series have antibacterial properties and have also recently been reported as KAT II inhibitors. The key nitrophenyl alanine intermediates are prepared enantioselectively in excellent yield by phase transfer ...