2-(1-Alkenyl)- and 2-aryl-substituted four-membered cyclic nitrones as precursors for 2,3,4-substituted pyridines and quinolines

Willem Verboom, P.J.S.S. van Eijk, P.G.M. Conti, David Reinhoudt

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Abstract

Reaction of the 2-(1-alkenyl)-substituted four-membered cyclic nitrones 3 with KOtBu gave the corresponding α,β-γ,δ-unsaturated oximes 6 which were converted into the substituted pyridines 9 , either by azeotropic removal of water in refluxing benzene or by reactfon in a 1:1 mixture of acetic anhydride and acetic acid at room temperature. Treatment of pyridine 9c with boron tribromide afforded the benzopyrano[4,3-c]pyridine derivatte 10. Reaction of the 2-aryl-substituted four-membered cyclic nitrones 4 with acetyl chloride yielded the 0 -acetylated oximes 12 which cyclized upon irradiation to the 2,3,4-substituted quinolines 14.
Original languageUndefined
Pages (from-to)3131-3138
JournalTetrahedron
Volume45
Issue number10
DOIs
Publication statusPublished - 1989

Keywords

  • IR-70493

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