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Inactivation path during the copper (II) catalyzed synthesis of Questiomycin A from oxidation of 2-aminophenol

Paper ID Volume ID Publish Year Pages File Format Full-Text
40621 45860 2012 7 PDF Available
Title
Inactivation path during the copper (II) catalyzed synthesis of Questiomycin A from oxidation of 2-aminophenol
Abstract

The catalytic oxidation of 2-aminophenol (OAP) to 2-amino-3H–phenoxazin-3-one (APX, Questiomycin A) was the object of numerous studies partly due to antimicrobial properties of Questiomycin A and mostly because it can be used as a model for the synthesis of the naturally occurring antineoplastic agent Actinomycin D. Several copper complexes were used as dioxygen and/or substrates activators in order to mimic the activity of phenoxazinone synthase, but the reported assays failed to provide reasonable mechanistic features in media compatible with natural conditions. The main purposes of our work were to use simple copper salts to perform oxidation of OAP in oxygenated aqueous solutions and to develop a reaction scheme able to explain the low yields in APX along with the operational inactivation of the catalyst. A 11-step kinetic model able to describe the inactivation of copper(II) catalyst during oxidation of OAP to APX in oxygenated solutions was developed, and the rate constants for both catalytic and non-catalytic branch were estimated either experimentally or using a computing program for detailed kinetic simulation. It was demonstrated that the inactivation path can be assigned to formation of the stable bis(o-iminosemiquinonato)copper(II) complex, a compound reported as a moderate antimicrobial agent.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (81 K)Download as PowerPoint slideHighlight► The catalytic oxidation of OAP to APX was achieved in the presence of simple copper salts. ► Low yields in APX and operational inactivation of the catalyst were observed. ► The inactivation path can be assigned to formation of a stable copper(II)–OAP complex. ► A 11-step kinetic model able to describe the inactivation of copper(II) catalyst was proposed.

Keywords
2-Aminophenol; Oxidation; Questiomycin A; Kinetic modelling; Copper(II) complex
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Inactivation path during the copper (II) catalyzed synthesis of Questiomycin A from oxidation of 2-aminophenol
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 447–448, 7 December 2012, Pages 74–80
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us