synthesis of highly substituted oxazoles through iodine(iii)-mediated reactions of ketones with nitriles通过碘合成高取代唑酮与腈(iii)介导的反应.pdfVIP

Molecules 2012, 17, 11046-11055; doi:10.3390/molecules170911046 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of Highly Substituted Oxazoles through Iodine(III)-Mediated Reactions of Ketones with Nitriles Akio Saito †,*, Nao Hyodo and Yuji Hanzawa * Laboratory of Organic Reaction Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan; E-Mail: a06097@ug.shoyaku.ac.jp † Current address: Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei-shi, Tokyo 184-8588, Japan. * Authors to whom correspondence should be addressed; E-Mails: akio-sai@cc.tuat.ac.jp (A.S.); hanzaway@ac.shoyaku.ac.jp (Y.H.); Tel./Fax: +81-42-721-1569 (Y.H.). Received: 6 August 2012; in revised form: 29 August 2012 / Accepted: 10 September 2012 / Published: 13 September 2012 Abstract: In the presence of trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethane- sulfonyl)imide (Tf NH), iodosobenzene (PhI=O) efficiently promoted the reactions of 2 dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions. Keywords: single-step synthesis; iodine(III); oxazole; ketone; nitrile 1. Introduction The synthesis of oxazole compounds has attracted a great deal of attention due to the widespread application of oxazole derivatives in biologically ac