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

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 compoun...

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Bibliographic Details
Published in	Tetrahedron Vol. 65; no. 34; pp. 7048 - 7055
Main Authors	Giomi, Donatella, Piacenti, Michela, Alfini, Renzo, Brandi, Alberto
Format	Journal Article
Language	English
Published	OXFORD Elsevier Ltd 22.08.2009 Elsevier
Subjects	Allyl pyridyl alcohol derivatives Chemistry Chemistry, Organic Exact sciences and technology Hantzsch ester 1,4-dihydropyridine mimics Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Nitro derivatives metal-free reductions Nucleophilic substitutions Organic chemistry Physical Sciences Preparations and properties Science & Technology Nucleophilic substitutions Hantzsch ester 1,4-dihydropyridine mimics Allyl pyridyl alcohol derivatives Nitro derivatives metal-free reductions ISOMERIZATION COMPLEXES REACTIVITY PYRIDINES KETONES ALLYLIC ALCOHOLS CARBON NUCLEOPHILES METAL DERIVATIVES Nitro compound Nitrogen heterocycle Alcohol Metal Thermal reaction Allylic compound Pyridine derivatives Chemical reduction Organic synthesis Aromatic compound Dihydropyridine derivatives Chemical synthesis Electrophile Hydrogen transfer Regioselectivity Acidity Tautomer Experimental study Pyridine Biomimetic compound Reagents Nucleophilic substitution Nucleophile
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ISSN	0040-4020 1464-5416
DOI	10.1016/j.tet.2009.06.044

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Summary:	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. ▪
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2009.06.044