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J Org Chem. 2011 May 6;76(9):3484-97. doi: 10.1021/jo200530j. Epub 2011 Apr 11.

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

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1
Neuroscience Chemistry, Pfizer Worldwide R&D, Eastern Point Rd., Groton, Connecticut 06340, USA. laura.mcallister@pfizer.com

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 catalyzed alkylation of the corresponding nitrobenzyl bromides. The scope and limitations of the reductive cyclization transformation have been explored with attention to the effects of substitution pattern and electronics on reaction efficiency and byproduct formation. In addition, a novel activated trifluoroethyl ester cyclization strategy has been developed as an alternate approach to the most sterically demanding systems in this series.

PMID:
21452845
DOI:
10.1021/jo200530j
[Indexed for MEDLINE]
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