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.

1-(2-Pyridyl)-2-propen-1-ol: a multipurpose reagent in organic synthesis / D. Giomi; M. Piacenti; R. Alfini; A. Brandi. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 65:(2009), pp. 7048-7055. [10.1016/j.tet.2009.06.044]

1-(2-Pyridyl)-2-propen-1-ol: a multipurpose reagent in organic synthesis

GIOMI, DONATELLA;ALFINI, RENZO;BRANDI, ALBERTO
2009

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.
65
7048
7055
D. Giomi; M. Piacenti; R. Alfini; A. Brandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/367889
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