Convenient one-pot synthesis of fluorinated DHPs derivatives and their further transformations

✍ Scribed by Pengyuan Wang; Liping Song; Hai Yi; Min Zhang; Shizheng Zhu; Hongmei Deng; Min Shao

• Book ID: 104097891
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 392 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.05.110

✦ Synopsis

One-pot four-component reactions of aromatic aldehyde, Meldrum's acid, ethyl-4,4,4-trifluoro-1,3dioxobutanoate, and ammonium acetate afford ethyl 2-hydroxy-6-oxo-4-aryl-2-(trifluoromethyl)piperidine-3-carboxylate in good yields. The one-pot four-component process consists of an initial Michael addition, and a subsequent intramolecular cyclization. The effect of solvents on the reaction efficiency and yield is briefly investigated. The structure of product is further confirmed by XRD analysis. Meanwhile, the further transformation of hemi-aminal moiety to the corresponding dehydrated product is also achieved under the mild reaction conditions. The possible mechanism for the formation of product is presented.