A novel ambident reactivity of azolylacroleins

Reaction of azolylacroleins with phosphoranes bearing a conjugated double bond was found to yield either azolyltrienes in a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambiden...

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Bibliographic Details
Published inTetrahedron Vol. 63; no. 22; pp. 4730 - 4736
Main Authors Nagy, Ildikó, Hajós, György, Riedl, Zsuzsanna, Egyed, Orsolya, Pápai, Imre
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.05.2007
Elsevier
Subjects
Ab initio calculation
Azolyltriene
Chemistry
Chemistry, Organic
Phosphorane
Physical Sciences
Science & Technology
Wittig reaction
Wittig reaction
Ab initio calculation
Azolyltriene
Phosphorane
ab initio calculation
ROUTE
azolyltriene
phosphorane
FACILE
DERIVATIVES
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Summary:Reaction of azolylacroleins with phosphoranes bearing a conjugated double bond was found to yield either azolyltrienes in a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambident reactivity was found to be dependent on the substituent of the phosphorane, which was rationalized by ab initio (DFT) calculation of the atomic charges of the reaction centres. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.03.098