Flash vacuum pyrolysis of 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2-vinyl-1H-pyrroles |
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Authors: | Maria IL Soares |
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Institution: | Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal |
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Abstract: | The flash vacuum pyrolysis of new 1,1-dimethyl- and 1-methyl-1H,3H-pyrrolo1,2-c]thiazole-2,2-dioxides gave penta-substituted 2-vinyl-1H-pyrroles via sigmatropic 1,8]-H shift of the corresponding azafulvenium methide intermediates. In some cases these 1H-pyrroles underwent rearrangement to 2-allyl-1H-pyrroles. Di-substituted 2-vinylpyrroles have also been prepared and their reactivity studied. Under FVP N-benzyl-pyrrol-2-ylpropenoates were converted into 3H-pyrrolizin-3-ones. On the other hand, microwave-assisted reaction of 1-benzyl-2-vinyl-1H-pyrrole gave a 4,5,6,7-tetrahydro-1H-indole derivative. |
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Keywords: | Pericyclic reactions Flash vacuum pyrolysis Azafulvenium methides Diazafulvenium methides 2-Allyl-1H-pyrroles 3H-Pyrrolizin-3-ones Tetrahydro-1H-indole Microwave-assisted reactions |
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