| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5226052 | Tetrahedron | 2009 | 8 Pages |
Abstract
A peculiar thermal behaviour of hydroxyallylpyridyl derivatives, likely associated to the weak acidity of the 'picoline-type' hydrogen atom and responsible for the formation of allyl inversion products, has been reported. The 'mobility' of the same hydrogen atom allowed the unprotected title compound to behave regioselectively as C-1, C-2 or C-3 carbon nucleophile depending on the thermal or base-promoted experimental conditions and on the kind of electrophile; moreover, the corresponding Hantzsch-type pyridine tautomer displayed a biomimetic ability to transfer hydrogen to aromatic and heteroaromatic nitro derivatives.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Donatella Giomi, Michela Piacenti, Renzo Alfini, Alberto Brandi,