Document details

N-Vinyl- and C-Vinylpyrroles from Azafulvenium Methides. Flash Vacuum Pyrolysis...

Author(s): Melo, Teresa M. V. D. Pinho e cv logo 1 ; Soares, Maria I. L. cv logo 2 ; Gonsalves, António M. d'A. Rocha cv logo 3 ; Paixão, José A. cv logo 4 ; Beja, Ana Matos cv logo 5 ; Silva, Manuela Ramos cv logo 6

Date: 2005

Persistent ID: http://hdl.handle.net/10316/10278

Origin: Estudo Geral - Universidade de Coimbra


Description
1-Azafulvenium methides, generated from pyrrolo[1,2-c]thiazole-2,2-dioxides' thermal extrusion of sulfur dioxide, led to the synthesis of functionalized pyrroles. The intramolecular trapping of these transient 8π 1,7-dipoles in pericyclic reactions, namely sigmatropic [1,8]H shifts and 1,7-electrocyclization, allowed the synthesis of N-vinylpyrroles and C-vinylpyrroles which, under flash vacuum pyrolysis conditions, are converted into 5-oxo-5H-pyrrolizines or 4-oxo-1,4-dihydro-1-aza-benzo[f]azulenes, respectively. These heterocycles can also be obtained directly from FVP of pyrrolo[1,2-c]thiazole 2,2-dioxides. The synthesis and X-ray structure of a new 6-oxocyclopenta[b]pyrrole derivative is also reported.
Document Type Article
Language English
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