Combined Intra-Intermolecular Criss-Cross Cycloaddition Reactions Leading to Perfluoroalkylated Fused Tricyclic Nitrogen Heterocycles

• Autoři: HARNISCH Francois-Xavier; GALETA Juraj; HARAKAT Dominique; POTÁČEK Milan; BOUILLON Jean-Philippe
• Rok publikování: 2014
• Druh: Článek v odborném periodiku
• Časopis / Zdroj: Journal of Fluorine Chemistry
• Fakulta / Pracoviště MU: Přírodovědecká fakulta
• www: http://www.sciencedirect.com/science/article/pii/S0022113913003862
• Doi: http://dx.doi.org/10.1016/j.jfluchem.2013.12.004
• Obor: Organická chemie
• Klíčová slova: Fluorine; Fused nitrogen heterocycles; Non-symmetrical azines; Criss-cross cycloaddition
• Popis: Blocked hydrazines were prepared by the reaction of diethyl hydrazinophosphate with fluorinated aldehydes applying Zwierzak’s method and then introduced into the reaction with 3-substituted homoallenyl aldehydes. The resulting non-symmetrical fluorine containing azines reacted in combined intra-intermolecular criss-cross cycloaddition with phenyl isocyanate, phenyl isothiocyanate and dimethyl acetylenedicarboxylate producing fused tricyclic heterocycles. Besides, an interesting cyclization of fluorinated non-symmetrical azines without any dipolarophile initiated by heating was carried out providing fused bicyclic systems.

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