Synthesis and Biological Evaluation of New Naphthoquinones Derivatives by Catalytic Oxidation

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.