Synthesis of new 4-(1-ethylthio-2,2,2-trifluoroethyl)-6-methylpyridazin-3(2H)-ones starting from S-ethyl 4-oxo-2-(pentafluoroethyl)pentanethiolate and hydrazines |
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Authors: | Vasile Dinoiu Bernard Tinant Jean-Philippe Bouillon |
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Affiliation: | a Laboratoire Sciences et Méthodes Séparatives (SMS), EA 3233, Université de Rouen, IRCOF, F-76821 Mont-Saint-Aignan Cedex, France b Romanian Academy, Institute of Organic Chemistry “C.D. Nenitzescu”, Spl. Independentei 202B, 77141 Bucharest, Romania c Unité de Chimie Structurale et des Mécanismes Moléculaires, Université Catholique de Louvain, 1 Place Louis Pasteur, B-1348 Louvain-la-Neuve, Belgique d Laboratoire de Pharmacognosie, UMR CNRS 6013, Université de Reims, Faculté des Sciences, Bâtiment 18, Moulin de la Housse, B.P. 1039, F-51687 Reims Cedex 2, France |
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Abstract: | The paper presents a one-pot conversion of γ-keto-α-pentafluoroethyl thioester into new pyridazin-3-ones and α,β-unsaturated lactams. The structures of all new compounds were ascribed using 1D (19F, 1H, 13C) and 2D (1H-15N) NMR data, and X-ray diffraction analysis. Two possible competitive reaction mechanisms for the synthesis of pyridazin-3-ones and lactams are presented. |
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Keywords: | Trifluoromethyl γ-Ketothioester Furan Lactam Pyridazinone |
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