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Oxalic acid catalysed chromium(VI) oxidation of some 2-amino-4,6-diarylpyrimidines

Paper ID Volume ID Publish Year Pages File Format Full-Text
52716 46882 2007 6 PDF Available
Title
Oxalic acid catalysed chromium(VI) oxidation of some 2-amino-4,6-diarylpyrimidines
Abstract

Some 2-amino-4,6-diarylpyrimidines (APM), synthesized from chalcones and guanidine hydrochloride in presence of alkali by microwave irradiation in solvent-free conditions, were subjected to oxidation with chromium(VI)–oxalic acid complex (Cr(VI)–Oxa) in highly acidic solutions. Oxalic acid (Oxa) offers the reaction a more favourable pathway and in the absence of oxalic acid the reaction is sluggish. The depletion of chromium(VI) shows a complicated kinetics involving a fast reaction to about 35% consumption followed by a slow one. Low dielectric constant of the medium facilitates the reaction. The investigations with 2-amino-6-(4-nitrophenyl)- 4-phenylpyrimidine and 2-amino-6-(4-methoxyphenyl)-4-phenylpyrimidine reveal that, irrespective of the nature of the substituents, the rates are higher than for the parent. APM is catalytically converted to the unusual product 3-hydroxy-1,3-diphenyl-propan-1-one. Consideration of the kinetic behaviours under different experimental conditions and the product assignment provide valuable mechanistic insight into the system studied.

Keywords
Oxalic acid; 2-Aminopyrimidine; Kinetics; Oxidation; Chromium(VI)
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Oxalic acid catalysed chromium(VI) oxidation of some 2-amino-4,6-diarylpyrimidines
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 8, Issue 4, April 2007, Pages 713–718
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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