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

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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

Citace
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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