New reactivity of 1-(2-pyridyl)-2-propen-1-ol with nitro derivatives |
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| Authors: | Donatella Giomi Renzo Alfini Alberto Brandi |
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| Institution: | Dipartimento di Chimica Organica ‘Ugo Schiff’, Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamenti Attivi (HeteroBioLab), Università di Firenze, Polo Scientifico e Tecnologico, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy |
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| Abstract: | 1-(2-Pyridyl)-2-propen-1-ol showed an unprecedented reactivity behaving as Hantzsch ester 1,4-dihydropyridine mimic for the metal-free reduction of the nitro group of electron-deficient aromatic and heteroaromatic nitro compounds to the corresponding amino function. The redox mechanism is part of a domino process involving a direct trapping of the amino derivatives through aza-Michael addition to the vinyl ketone intermediate leading to the one-pot formation of new functionalised aminoacylpyridines. |
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| Keywords: | Allyl pyridyl alcohols Hantzsch ester 1 4-dihydropyridine mimic Nitro derivatives Metal-free reductions |
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