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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/36631
Title: 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
URI: http://hdl.handle.net/10261/36631
ISSN: 0002-7863
DOI: 10.1021/ja1006614
E-ISSN: 1520-5126
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