Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions |
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Authors: | Maria I.L. Soares |
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Affiliation: | Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal |
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Abstract: | Azafulvenium methides and diazafulvenium methides have been generated under microwave irradiation from 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2,2-dioxo-1H,3H-pyrazolo[1,5-c]thiazoles, respectively. Pericyclic reactions of these 1,7-dipole intermediates, namely, sigmatropic [1,8]H shifts, 1,7-electrocyclization or [8π+2π] cycloaddition led to the synthesis of a range of pyrrole and pyrazole derivatives. The first evidence for the azafulvenium methides by intermolecular trapping via [8π+2π] cycloaddition is reported. |
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Keywords: | Azafulvenium methide Diazafulvenium methide Pyrrole Pyrazole Sigmatropic [1,8]H shifts 1,7-Electrocyclization [8π+2π] Cycloaddition |
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