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

Vasile Dinoiu; Bernard Tinant; Jean-Marc Nuzillard; J.-P. Bouillon

doi:10.1016/j.jfluchem.2005.11.001

Journal articles

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

Vasile Dinoiu ^{1, 2} Bernard Tinant ³ Jean-Marc Nuzillard ⁴ J.-P. Bouillon ¹

1 SMS - Sciences et Méthodes Séparatives

2 ROMANIAN ACADEMY - Institute of Organic Chemistry, C.D. Nenitzescu

3 UCL - Université Catholique de Louvain

4 Laboratoire de Pharmacognosie

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.

Keywords : Trifluoromethyl γ-Ketothioester Furan Lactam Pyridazinone

Document type :

Journal articles

Domain :

Chemical Sciences

Chemical Sciences / Organic chemistry

Chemical Sciences / Material chemistry

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https://hal-normandie-univ.archives-ouvertes.fr/hal-01935486
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Submitted on : Monday, November 26, 2018 - 5:05:21 PM
Last modification on : Monday, December 2, 2019 - 2:44:05 PM

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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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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