New reactivity of 1-(2-pyridyl)-2-propen-1-ol with nitro derivatives

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...

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Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 49; pp. 6977 - 6979
Main Authors Giomi, Donatella, Alfini, Renzo, Brandi, Alberto
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.12.2008
Elsevier
Subjects
Allyl pyridyl alcohols
Chemistry
Chemistry, Organic
Hantzsch ester 1,4-dihydropyridine mimic
Metal-free reductions
Nitro derivatives
Physical Sciences
Science & Technology
Allyl pyridyl alcohols
Hantzsch ester 1,4-dihydropyridine mimic
Nitro derivatives
Metal-free reductions
HYDROGENATION
REDUCTION
REDUCING AGENT
CHEMISTRY
ORGANOCATALYSIS
HANTZSCH 1,4-DIHYDROPYRIDINE ESTER
DIHYDROPYRIDINES
Online AccessGet full text
ISSN0040-4039
1873-3581
DOI10.1016/j.tetlet.2008.09.105

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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.09.105