A One-Pot Synthesis of Functionalised 3-pyrolin-2-ones by a four-component reaction between Triphenylphosphine,Primary Amines,Dimethyl Acetylenedicarboxylate and Ethyl Chlorooxoacetate
Free accessResearch articleFirst published online October, 2007
A One-Pot Synthesis of Functionalised 3-pyrolin-2-ones by a four-component reaction between Triphenylphosphine,Primary Amines,Dimethyl Acetylenedicarboxylate and Ethyl Chlorooxoacetate
Reaction between triphenylphosphine, dimethy acetylenedicarboxylate and amines produces phosphorus ylids which undergo a smooth reaction with ethyl chlorooxoacetate and triethylamine to produce dimethyl N-aryl-(or alkyl)-4-ethoxy-5-oxo-2,5-dihydro-1H-pyrole-2,3-dicarboxylates in high yields.
KakeyaH., OnozawaC., SatoM., AraiK., and OsadaH., J. Med. Chem., 1997, 40, 391, and references therein.
2.
(a) KulkaraniB.A., and GanesanA., Angew. Chem. Int. Ed. Engl., 1997, 36, 2454; (b) S. Bienz, C. Busacca and A.I. Mayers, J. Am. Chem. Soc., 1989, 111, 1905; (c) B. Tarnchompoo, C. Thebtaranonth and Y. Thebtaranonth, Tetrahedron Lett., 1987, 28, 6675.
3.
BarluengaJ., PalaciosF., FusteroS., and GotorV., Synthesis, 1981, 200.
4.
(a) BakerJ.T., and SifniadesS., J. Org. Chem., 1979, 44, 2798; (b) Z.D. Josef and J. Tufariello, Synth. Commun., 1990, 20, 227.
5.
YavariI., AdibM., and HojabriL., Tetrahedron, 2002, 58, 7213.
6.
Anary-abbasinejadM., and AscarrianN., J. Chem. Res., 2007, 11.
7.
Anary-AbbasinejadM., RostamiN., ParhamiA., and HassanabadiA., J. Chem. Res., 2007, 257.
8.
Anary-abbasinejadM., and TahanS., Phosphorus, Sulfur and Silicon, 2007, 315.
9.
Anary-AbbasinejadM., HassanabadiA., and Anaraki-ArdakaniH., J. Chem. Res., 2007, 455.
10.
Anary-AbbasinejadM., and HassanabadiA., J. Chem. Res., 2007, 475.
11.
YavariI., and BayatM., Synthetic Commun., 2002, 32, 2527.
