Synthesis of (2,2,2-trifluoroethyl) substituted pyridazin-3(2H)-ones and 1,5-dihydropyrrol-2-ones from α,β-unsaturated γ-lactones and hydrazines

This paper presents the transformation of α,β-unsaturated γ-lactones into 2,2,2-trifluoroethyl substituted pyridazin-3(2H)-ones and 1,5-dihydropyrrol-2-ones starting from various hydrazines. The influence of the γ-lactone substitution (sulfanyl versus sulfonyl moiety) and the nature of the hydrazines (unsubstituted, alkyl- or aryl-substituted) on the outcome of the reaction were studied. All new heterocycles were characterized using 1D NMR, IR, MS and their data was compared with those of two reported X-ray diffraction structures. The two possible competitive pathways leading to pyridazin-3(2H)-ones and/or 1,5-dihydropyrrol-2-ones are discussed. Abinitio DFT calculations were also performed in order to rationalize several experimental results.

Graphical abstractThe paper presents the transformation of α,β-unsaturated γ-lactones into 2,2,2-trifluoroethyl substituted pyridazin-3(2H)-ones and 1,5-dihydropyrrol-2-ones starting from various hydrazines. The influence of γ-lactone substitution (sulfanyl versus sulfonyl moiety) and the nature of hydrazines (unsubstituted, alkyl- or aryl-substituted) on the outcome of the reaction were studied. All new heterocycles were characterized using 1D NMR, IR, MS and their data were compared with those of two reported X-ray diffraction structures. The two possible competitive pathways leading to pyridazin-3(2H)-ones and/or 1,5-dihydropyrrol-2-ones are discussed. Abinitio DFT calculations were also performed in order to rationalize few experimental results.Figure optionsDownload full-size imageDownload as PowerPoint slide