A General Strategy for the Synthesis of Cyclic N-Aryl Hydroxamic Acids via Partial Nitro Group Reduction was written by 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.. And the article was included in Journal of Organic Chemistry in 2011.Computed Properties of C37H37BrN2O This article mentions the following:
We describe a generalized approach to stereocontrolled synthesis of substituted cyclic hydroxamic acids (3-amino-1-hydroxy-3,4-dihydroquinolinones), e.g. I (R = F3CO, MeO, Me, Cl), 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. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Computed Properties of C37H37BrN2O).
(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. The development of synthetic approaches for efficient construction of novel quinuclidine derivatives is of great significance. Traditionally, quinuclidine scaffolds can be constructed by second-order nucleophilic substitution (SN2) reaction or condensation reaction of piperidine derivatives. However, most of these reactions are racemic or chiral auxiliary-assisted processes.Computed Properties of C37H37BrN2O
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider