A General Strategy for the Synthesis of Cyclic N-Aryl Hydroxamic Acids via Partial Nitro Group Reduction

• Published in: Journal of organic chemistry Vol. 76; no. 9; pp. 3484 - 3497
• Main Authors: 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
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.05.2011; Amer Chemical Soc
• Subjects: Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Chemistry; Chemistry, Organic; Cyclization; Esters; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Hydroxamic Acids - chemical synthesis; Hydroxamic Acids - chemistry; Medical sciences; Nitro Compounds - chemistry; Organic chemistry; Oxidation-Reduction; Pharmacology. Drug treatments; Phenylalanine - analogs & derivatives; Phenylalanine - chemical synthesis; Phenylalanine - chemistry; Physical Sciences; Preparations and properties; Science & Technology; Sodium Acetate - chemistry; Substrate Specificity; Tin Compounds - chemistry; PHASE-TRANSFER; Phase transfer catalysis; Substituent effect; Nitro compound; Enantioselectivity; Nitrogen heterocycle; Selectivity; Alkylation; Chemical reduction; Stereoselectivity; Ester; Amine; Aromatic compound; Chemical synthesis; Quinolone derivatives; Alanine; Phenylalanine; Hydroxamic acid; Quinoline derivatives; Organic bromine compounds; α-Aminoacid; Cyclization; Cyclic compound; Aminoacid; Inhibitor; Antibacterial agent

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 bee...