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Paper | Special issue | Vol 70, No. 1, 2006, pp.261-270
Published online, 5th September, 2006
DOI: 10.3987/COM-06-S(W)17
Selective 1,2- vs 1,4-Addition of N-Arylphosphazenes to β,γ-Unsaturated α-Ketoesters. Synthesis of Quinolinecarboxylates

Francisco Palacios,* Javier Vicario, Jesús M. de los Santos, and Domitila Aparicio

*Department of Organic Chemistry I, Faculty of Pharmacy, University of The Basque Country, P.O. Box 450, 01080 Vitoria, Spain

Abstract

Selective conjugate reaction (1,4 addition) of N-arylphosphazenes derived from triphenylphosphine to α,β-unsaturated carbonyl compounds yielded 2-quinolinecarboxylates. However, when more reactive phosphazene species derived from trimethylphosphine were used, selective reaction with the carbonyl carbon (1,2-addition) occurred and N-aryl 1-azadienes were obtained. Thermal 6π-azaelectrocyclization of these 1-azadienes afforded 4-quinolinecarboxylates.