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Article Dans Une Revue Journal of Fluorine Chemistry Année : 2014

Combined intra-intermolecular criss-cross cycloaddition reactions leading to perfluoroalkylated fused tricyclic nitrogen heterocycles

Résumé

Perfluoroalkylated hydrazones 1a–ewere preparedfrom diethyl hydrazinophosphate andwere engaged in the reaction with 3-substitutedhomoallenyl aldehydes according to Zwierzak’smethod. The resulting non-symmetrical perfluoroalkyl-derived azines reacted in combined intra-intermolecular criss-cross cycloaddition with phenyl isocyanate, phenyl isothiocyanate and dimethyl acetylenedicarboxylate producing fused tricyclic heterocycles. Besides, the thermal cyclization of perfluoroalkylated non- symmetrical azines, without added dipolarophile, was carried out providing fused bicyclic systems.
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Dates et versions

hal-01149598 , version 1 (07-05-2015)

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François-Xavier Harnisch, Juraj Galeta, Dominique Harakat, Milan Potacek, J.-P. Bouillon. Combined intra-intermolecular criss-cross cycloaddition reactions leading to perfluoroalkylated fused tricyclic nitrogen heterocycles. Journal of Fluorine Chemistry, 2014, 158, pp.38-43. ⟨10.1016/j.jfluchem.2013.12.004⟩. ⟨hal-01149598⟩
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