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Closed Access item Selective Synthesis of N-Substituted 1,2-Dihydropyridines from Furans by Copper-Induced Concurrent Tandem Catalysis

Authors:Fructos, Manuel R.
Álvarez, Eleuterio
Díaz-Requejo, M. Mar
Pérez, Pedro J.
Keywords:Pyridine derivatives, Ring closure reactions
Issue Date:15-Mar-2010
Publisher:American Chemical Society
Citation:Journal of the American Chemical Society 132(13): 4600-4607 (2010)
Abstract:A novel transformation in which mono- or dialkyl-substituted furans are converted into 1,2-dihydropyridines upon reaction with PhI═NTs at room temperature is reported. The reaction is catalyzed by complexes of general formula TpxM (M = Cu, Ag) and consists of a one-pot procedure with four consecutive catalytic cycles. Furan aziridination is followed by aziridine ring-opening, transimination reaction, inverse-electronic-demand aza-Diels−Alder reaction, and a final hydrogen elimination reaction. The mechanism of the overall transformation is proposed where the metal complex displays a crucial role along the reaction pathway.
Description:8 páginas, 4 figuras, 1 tabla, 9 esquemas
Publisher version (URL):http://dx.doi.org/10.1021/ja1006614
E-ISSNmetadata.dc.identifier.doi = DOI:1520-5126
Appears in Collections:(IIQ) Artículos

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