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Title: Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
Authors: Soares, Maria I. L. 
Melo, Teresa M. V. D. Pinho e 
Keywords: Azafulvenium methide; Diazafulvenium methide; Pyrrole; Pyrazole; Sigmatropic [1,8]H shifts; 1,7-Electrocyclization; [8[pi]+2[pi]] Cycloaddition
Issue Date: 2008
Citation: Tetrahedron Letters. 49:33 (2008) 4889-4893
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 [8[pi]+2[pi]] cycloaddition led to the synthesis of a range of pyrrole and pyrazole derivatives. The first evidence for the azafulvenium methides by intermolecular trapping via [8[pi]+2[pi]] cycloaddition is reported.
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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