Efficient Deallylation of Allyl Phenyl Ethers by Molecular Iodine in PEG-400 and Their Utility for Flavone Synthesis

<div><p></p><p>Rapid and efficient deallylation of allyl phenyl ethers by molecular iodine (20 mol%) in polyethylene glycol-400 at 60 °C has been reported. This method has short reaction time, readily available catalyst, and reuse of reaction medium with good yield. The utility of this methodology has been extended to flavone synthesis.</p> <p>[Supplementary materials are available for this article. Go to the publisher's online edition of <i>Synthetic Communications®</i> for the following free supplemental resource(s): Full experimental and spectral details.]</p> </div

A One-Pot Direct Iodination of the Fischer–Borsche Ring Using Molecular Iodine and Its Utility in the Synthesis of 6‑Oxygenated Carbazole Alkaloids

An efficient regioselective iodination of the Fischer–Borsche ring has been achieved using molecular iodine, in a one-pot synthesis. The acid-, metal-, and oxidant-free conditions of the present method are highly convenient and practical. Furthermore, the one-pot direct iodination process is extended to the concise synthesis of glycozoline, 3-formyl-6-methoxy-carbazole, and 6-methoxy-carbazole-3-methyl­carboxylate natural alkaloids. This method has been proven to be tolerant to a broad range of functional groups, with good to excellent yields

Copper (II) chloride: A regioselective catalyst for oxidative aromatization of pyrazoline, isoxazoline and 3-methyl flavanones

1091-1097A new protocol has been reported in which a series of pyrazoline, isoxazoline and 3-methyl flavanone has been conveniently aromatized by using CuCl2.2H2O in DMSO within a short reaction time in excellent yields. The attraction of this new protocol is regioselective aromatization of substrate 3i-j and <b style="mso-bidi-font-weight: normal">5a-e which has been carried out to afford the aromatized product with O-allyl group intact in excellent yield

Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C–H Activation

The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and ¹⁸O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C–H activation were used as key steps in the formal total synthesis of antimalarial natural product isocryptolepine