Water–acetone Media Enforced Chemoselective Synthesis of 2-substituted Pyrrole Stable Phosphorus Ylides from Reaction between Pyrrole and Acetylenic Esters in the Presence of Triphenylphosphine
Free accessResearch articleFirst published online October, 2007
Water–acetone Media Enforced Chemoselective Synthesis of 2-substituted Pyrrole Stable Phosphorus Ylides from Reaction between Pyrrole and Acetylenic Esters in the Presence of Triphenylphosphine
Pyrrole undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine in a mixture of water–acetone (50:50) as a solvent pathway to produce phosphorus ylides of 2-substituted pyrrole in good yield.
(a) HallA., BitR.A., BrownS.H., ChaignotH.M., ChesselI.P., ColemanT., GiblinG.M.P., HurstD.N., KilfordI.R., LewellX.Q., MichelA.D., MohamedS., NaylorA., NovelliR., SkinnerL., SpaldingD.J., TangS.P., and WilsonR.J., Bioorg. Med. Lett., 2006, 16, 2666; (b) A. Lansiaux, L. Dassonneville, M. Facompre, A. Kumar, C.E. Stephens, M. Bajic, F. Tanious, W.D. Wilson, D.W. Boykin and C. Bailly, J. Med. Chem., 2002, 45, 1994; (c) K. Kikuchi, K. Tagami, S. Hibi, H. Yoshimura, N. Tokuhara, K. Tai, T. Hida, T. Yamauchi and M. Nagai, Bioorg. Med. Chem. Lett., 2001, 11, 1215; (d) M. Biava, G.C. Portea, D. Deidda, R. Pompei, A. Tafi and F. Marinetti, Bioorg. Med. Chem., 2003, 11, 515; (e) B. Jolicoeur, E.E. Chapman, A. Thompson and W.D. Lubell, Tetrahedron., 2006, 62, 11531.
2.
HudsonH.R., The Chemistry of Organophosphorus Compounds, Vol. 1. Primary, Secondary and Tertiary Phosphines and Heterocyclic Organophosphorus III Compounds; HartleyF.R. (ed.), Wiley, New York: 1990, pp. 382–472.
