Preparation of α,β-Unsaturated Ketones Bearing a Trifluoromethyl Group and Their Application in Organic Synthesis 英文参考文献.docVIP

Molecules 1997, 2, 186-232 molecules ISSN 1420-3049 Preparation of a ,b-Unsaturated Ketones Bearing a Trifluoromethyl Group and Their Application in Organic Synthesis Valentine G. Nenajdenko , Andrei V. Sanin, Elizabeth S. Balenkova * Department of Chemistry, Moscow State University, 119899 Moscow, Russia Tel.: +7 (095) 939-43-94; Fax: +7 (095) 932-88-46; E-mail: Nen@acylium.chem.msu.su Received: 9 December 1996 / Accepted: 28 March 1997 / Published: 1 December 1997 Abstract: The approaches to the synthesis of a ,b-unsaturated CF3-containing ketones and their use in organic chemistry are reviewed. The synthetic applications of these ketones are discussed. The formation of 4-, 5-, 6- and 7-membered heterocycles bearing a CF3 group based on reactions of a ,b-unsaturated CF3-containing ketones with different nucleophiles are discussed. Keywords: a ,b-Unsaturated trifluoromethyl ketones, CF3-containing heterocycles, trifluoroacetylation, synthesis, review. Introduction approaches to the synthesis of CF3-containing heterocycles are based on the use of b-dicarbonyl Organofluorine compounds, particularly heterocyclic compounds [10, 11]. Cycloaddition reactions (using trifluoromethylalkenes ones, are very attractive targets both from a theoretical and synthetic point of view. They have attracted much attention especially in the last decade in biological and medicinal chemistry [1]. This is due to the unique features [12], trifluoroacetonitrileoxide [13]or trifluoroacylketenes [14]) were also widely used in recent years. However, the disadvantages of these methods, e.g. availability of starting compounds or utilization of aggressive and highly toxic reagents, have stimulated the development of new methods for synthesis of trifluoromethylated heterocyclic compounds. Many of fluorine compounds and foremost their high physiol