Combined Intra-Intermolecular Criss-Cross Cycloaddition Reactions Leading to Perfluoroalkylated Fused Tricyclic Nitrogen Heterocycles
| Authors | |
|---|---|
| Year of publication | 2014 |
| Type | Article in Periodical |
| Magazine / Source | Journal of Fluorine Chemistry |
| MU Faculty or unit | |
| Citation | |
| Web | http://www.sciencedirect.com/science/article/pii/S0022113913003862 |
| Doi | http://dx.doi.org/10.1016/j.jfluchem.2013.12.004 |
| Field | Organic chemistry |
| Keywords | Fluorine; Fused nitrogen heterocycles; Non-symmetrical azines; Criss-cross cycloaddition |
| Description | 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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