Abstract
The catalytic utilization of hypervalent iodine reagents, largely in consideration of economical and environmental viewpoints, is a most attractive strategy due to their unique features as extremely useful oxidants, with mild, safe, and environmentally friendly characteristics. Oxidation reactions constitute of a number of important transformations in organic synthesis. They are widely in the productions of a variety pharmaceuticals and natural products, and their intermediates.[1] As oxidants, hypervalent iodine reagents have recently received much attention due to their low toxicity, mild reactivity, ready availability, high stability, easy handling, etc.[2] For examples, phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis (trifluoroacetate) (PIFA)-induced oxidations of phenols and related reactions have been applied to many total syntheses of biologically important natural products and their pivotal intermediates.[3] This study reports a new synthetic methodology that was optimized to prepare new naphthoquinones derivatives via catalytic oxidation. [1] Hoelderich , W. F., Kollmer, F. Pure Appl. Chem.2000, 72, 1273. [2] (a) Zhdankin, V. V. ; Stang, P. J. Chem. Rev. 2002, 102, 2523. (b) Tohma, H. ; Kita, Y. Adv. Synth. Catal. 2004, 346, 111. (c) Moriarty, R. M. J. Org. Chem, 2005, 70, 2893. (d) Wirth, T. Angew. Chem. Int. Ed. 2005, 44, 3656. (e) Ochiai, M. Chem. Rec. 2007, 7, 12. [3] a) Pouységu, L.; Deffieux, D.; Quideau, S. Hypervalent iodine-mediated phenol dearomatization in natural product synthesis. Tetrahedron. 2010, 66, 2235-2261.Available. b) Moriarty, R.; Prakash, O. Oxidation of phenolic compounds with organohypervalent iodine reagents in Organic Reactions. Wiley New York, 2001, 57, 327-415. C) Ladziata, U.; Zhdankin, V.V. Hypervalent iodine(V) reagents in organic synthesis. ARKIVOC, 2006, (ix), 26-58.
Highlights
Oxidation reactions constitute of a number of important transformations in organic synthesis
Phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis (PIFA)induced oxidations of phenols and related reactions have been applied to many total syntheses of biologically important natural products and their pivotal intermediates.[7,8,9]
This study reports a new synthetic methodology that was optimized to prepare new naphthoquinones derivatives 13-16 via catalytic oxidation
Summary
Synthesis and biological evaluation of new naphthoquinones derivatives by catalytic oxidation El-Mahdi Ourhzif 1,2,3, Caroline Decombat 4, Florence Caldefie-Chezet 4, Pierre Chalard 1, Yves Troin 1,*, Mostafa Khouili 3 and Mohamed Akssira 2, * 1 Université Clermont Auvergne, CNRS, SIGMA Clermont, ICCF, F-63000 Clermont–Ferrand, France 2 Université Hassan II Casablanca, FST, Laboratoire de Chimie Physique et Chimie Bio organique BP
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