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

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Verboom, W. and Eijk van, P.J.S.S. and Conti, P.G.M. and Reinhoudt, D.N. (1989) 2-(1-Alkenyl)- and 2-aryl-substituted four-membered cyclic nitrones as precursors for 2,3,4-substituted pyridines and quinolines. Tetrahedron, 45 (10). pp. 3131-3138. ISSN 0040-4020

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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.
Item Type:Article
Copyright:© 1989 Elsevier Science
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/70493
Official URL:http://dx.doi.org/10.1016/S0040-4020(01)80139-3
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