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(2-Pyridyl)phenyl methanol: a new reagent for metal-free reduction of nitro aromatic compounds
Authors:Donatella Giomi
Affiliation:Dipartimento di Chimica ‘Ugo Schiff’, Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamenti Attivi (HeteroBioLab), Università di Firenze, Polo Scientifico e Tecnologico, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, Italy
Abstract:As previously reported for 1-(2-pyridyl)-2-propen-1-ol, (2-pyridyl)phenyl methanol is able to react as hydrogen donor towards nitro aromatic and heteroaromatic compounds. Operating in the presence of methyl acrylate as an aza-Michael acceptor, a domino process involving reduction and conjugate addition steps allows the one pot formation of β-amino esters. The crucial role of the pyridine nucleus in making this purely thermal reactivity of carbinols possible has been shown.
Keywords:Pyridyl carbinols   Hantzsch ester 1,4-dihydropyridine mimics   Nitro derivatives   Metal-free reductions
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