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Title: N-Vinyl- and C-Vinylpyrroles from Azafulvenium Methides. Flash Vacuum Pyrolysis Route to 5-Oxo-5H-pyrrolizines and 1-Azabenzo[f]azulenes
Authors: Melo, Teresa M. V. D. Pinho e 
Soares, Maria I. L. 
Gonsalves, António M. d'A. Rocha 
Paixão, José A. 
Beja, Ana Matos 
Silva, Manuela Ramos 
Issue Date: 19-Aug-2005
Publisher: American Chemical Society
Citation: The Journal of Organic Chemistry. 70:17 (2005) 6629-6638
Abstract: 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.
ISSN: 0022-3263
DOI: 10.1021/jo050480i
Rights: openAccess
Appears in Collections:FCTUC Física - Artigos em Revistas Internacionais
FCTUC Química - Artigos em Revistas Internacionais

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