A novel ambident reactivity of azolylacroleins

作者:Nagy Ildiko; Hajos Gyoergy*; Riedl Zsuzsanna; Egyed Orsolya; Papai Imre
来源:Tetrahedron, 2007, 63(22): 4730-4736.
DOI:10.1016/j.tet.2007.03.098

摘要

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.

  • 出版日期2007-5-28