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Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives |
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| Authors: | Jun Zhang Weiguo Cao Liping Song Qun Qian Min Shao |
| Institution: | a Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, China b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China c Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China |
| Abstract: | l-Proline-catalyzed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines provide a novel method for preparation of ethyl-6-(arylamino)-2-hydroxy-4-phenyl-2-(trifluoromethyl)tetrahydro-2H-pyran-3-carboxylate derivatives in good yields. The reaction was conducted by initial Michael addition, followed by intra-molecular cyclization under mild conditions. The structure of a typical ethyl-2-hydroxy-4-phenyl-6-(m-tolylamino)-2-(trifluoromethyl)tetrahydro-2H-pyran-3-carboxylate (4h) was confirmed by XRD analysis. A plausible mechanism is presented. |
| Keywords: | One-pot three-component reaction Fluorinated heterocycles Functionalized tetrahydropyran |
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