Lactonization of epoxyendic anhydride in reactions with amines |
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Authors: | L. I. Kas’yan O. V. Krishchik I. N. Tarabara A. O. Kas’yan V. A. Pal’chikov |
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Affiliation: | 1. Dnepropetrovsk National University, per. Nauchnyi 13, Dnepropetrovsk, 49625, Ukraine 2. Ukrainian State University of Chemical Technology, Dnepropetrovsk, Ukraine 3. Institut für organische Chemie, Rheinisch-Westf?lische technische Hochschule, Aachen, Germany
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Abstract: | Reactions of exo-5,6-epoxybicyclo[2.2.1]hept-5-ene-endo-2,endo-3-dicarboxylic anhydride (epoxyendic anhydride) with acyclic, aromatic, heteroaromatic, and nonaromatic heterocyclic amines afforded the corresponding heterocyclization products, substituted exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.03,7]nonane-endo-9-carboxamides (oxabrendanes), whose structure was confirmed by the IR and 1H and 13C NMR (including two-dimensional) spectra. Other approaches to the tricyclic compounds were also examined, in particular via reactions of organic peroxy acids with amido acids obtained by aminolysis of endic anhydride. |
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