Journal ArticleDOI
Reduction of nitroarenes to anilines in basic alcoholic media
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TLDR
In this paper, two different processes have been identified, both initiated by the condensation between the nitrosoarene intermediate (the first product of the reduction reaction) and the product of oxidation of the solvent.Abstract:
Substituted nitrobenzenes are reduced by alkoxide ions in alcohols to the corresponding azoxy and aniline derivatives. The reaction leading to anilines has been investigated in detail. Two different processes have been identified, both initiated by the condensation between the nitrosoarene intermediate (the first product of the reduction reaction) and the product of oxidation of the solvent. The imino derivative thus formed (ArNCH–COR) may either undergo hydrolysis (to aniline) or form, through a series of redox processes, compounds containing the ArNH–CO moiety. These are also hydrolysed to anilines in a slower reaction.read more
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Journal ArticleDOI
Synthesis of indoles via ring closure of 2-alkylnitroaniline derivatives
Jan Bergman,Peter Sand +1 more
TL;DR: In this paper, a variety of nitroindoles have been prepared from imidate, amidine, and sec -anilide derivatives of 2-alkyl-3- or 5-nitroanilines by a base-induced cyclization promoted by dialkyl oxalates.
Journal ArticleDOI
(2-Pyridyl)phenyl Methanol: a New Reagent for Metal-free Reduction of Nitro Aromatic Compounds
TL;DR: In this article, the pyridine nucleus was shown to be crucial in making purely thermal reactivity of carbinols possible, operating in the presence of methyl acrylate as an aza-Michael acceptor, in a domino process involving reduction and conjugate addition steps.
Journal ArticleDOI
Efficient route for the synthesis of 3,4-cycloalkoxy-2,5-diethoxycarbonyl-thiophenes obtained with bulky alkyl dibromides using trialkylamines as base–solvent
TL;DR: In this article, new reaction conditions were investigated for dialkylizing diethyl 3,4-dihydroxy-2,5-thiophenedicarboxylate with sterically hindered alkyl-dibromides, using as reaction system DMF or only the trialkylamine as base-solvent.
Journal ArticleDOI
Palladium-catalyzed transfer hydrogenation of nitrobenzenes: investigation of the selectivity
TL;DR: Aromatic nitro compounds can be reduced via transfer hydrogenation in the presence of Pd on basic supports in alcoholic sodium hydroxide yielding not only the appropriate amine, but the azobenzene and azoxybenzene intermediates as well as mentioned in this paper.
Journal ArticleDOI
Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.
Yingwei Zhao,Yingwei Zhao,Haoran Zhu,Siyoung Sung,Donald J. Wink,Joseph M. Zadrozny,Tom G. Driver +6 more
TL;DR: In this article, exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive, and the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1-2-phenyl migration.