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New domino reaction. One pot synthesis of 4,7-dihydroxythioaurone derivatives from benzaldehydes and 4-acetyl-2-oxo-benz[1,3]oxathiole |
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| Authors: | Marek T. Konieczny Wojciech Konieczny Konstanty Wierzba Pawe? Sowiński |
| Affiliation: | a Department of Organic Chemistry, Medical University of Gdańsk, 80-416 Gdańsk, Poland b Hanno Research Center, Taiho Pharmaceutical Company, Hanno-city, Saitama 357-8527, Japan c Laboratory of Nuclear Magnetic Resonance Spectroscopy, Gdańsk University of Technology, 80-952 Gdańsk, Poland |
| Abstract: | A convenient synthesis of 4,7-dihydroxythioaurone derivatives by a one pot reaction of benzaldehydes with 4-acetyl-2-oxo-benz[1,3]oxathioles and piperidine acetate in DMSO is described. The structures of the compounds, including double bond geometry were proved unequivocally by NMR methods. The thioaurone ring system seems to be formed by three consecutive reactions: opening of the oxathiolone ring with piperidine, oxidation of the formed mercapto group with DMSO or/and air to disulfide, and condensation with aldehyde. |
| Keywords: | Thioaurones Synthesis of Structure of Domino reaction |
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