Free accessResearch articleFirst published online 2007-8
Stereoselective One-Pot Synthesis of Functionalised Phosphonates by three-component reaction between Trialkyl(aryl) Phosphites,Dimethyl Acetylenedicarboxylate and indan-1,3-dione or N,N ′-dimethylbarbituric acid
Protonation of the reactive intermediate produced in the reaction between trialkyl(aryl) phosphites and dimethyl acetylenedicarboxylate by CH- acids such as indane-1,3-dione and N,N′-dimethylbarbituric acid leads to functionalised phosphonates in good yields.
CorbridgeD.E.C., Phosphorus, An Outline of Chemistry, Biochemistry and Uses, 5th edn, Elsevier, Amsterdam, 1995.
3.
CadoganJ.I.G., Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979.
4.
HudsonH.R., in The Chemistry of Organophosphorus Compounds, Vol. 1. Primary, Secondary and Tertiary Phosphines, Polyphosphines and Heterocyclic Organophosphorus (III) Compounds, ed. HartleyF.R., Wiley, New York, 1990, pp. 386–472.
5.
CherkasovR.A., and PudovicM.A., Russ. Chem. Rev., 1994, 63, 1019.
6.
ArdoageA.R.III, and StewantC.A., Chem. Rev., 1994, 94, 1215.
7.
PietrusiewizK.M., and ZablockaM., Chem. Rev., 1994, 94, 1375.
8.
BestmannH.J., and VostrowskyO., Top. Curr. Chem., 1983, 109, 86.
9.
YavariI., Khorramabadi-ZadA., Rashidi-RanjbarP., and Fallah-Bagher-ShaidaiiH., J. Mol. Struct. (THEOCHEM), 1977, 155, 389.
10.
BurgadaR., LerouxY., and El KhoshniehY.O., Tetrahedron Lett, 1981, 22, 3533.
11.
JohnsonA.W., KaskaW.C., StarzewskiA.O., and DixonK.D.A., Ylides and Imines of Phosphorus (John Wiley & Sons), 1993, pp. 386–387.
12.
YavariI., Anary-AbbasinejadM., and HossainiZ., Org. Biomol. Chem., 2003, 3, 560.
13.
MaghsoodlouM.T., Habibi KhorassaniS.M., HeydariR, and Roastami CharatiF., J. Chem. Research, 2006, 364.
14.
MaghsoodlouM.T., Habibi KhorassaniS.M., RofoueiM.K., AdhamdoustS.R., and NassiriM., Arkivoc, 2006, 143.
15.
YavariI., MossleminM.H., and MontahaeiA.R., J. Chem. Res., 1998, 576.
16.
YavariI., and RamazaniA., Phosphorus, Sulfur and Silicon, 1997, 130, 73.
17.
Anary-abbasinejadM., and AscarrianN., J. Chem. Res., 2007, 11.
18.
Anary-AbbasinejadM., ParhamiA., RostamiN., and HassanabadiA., J. Chem. Res., 2007, in press.
19.
Anary-abbasinejadM., and TahanS., Phosphorus, Sulfur and Silicon, 2007, 2, 315.
20.
KarplusM., J. Am. Chem. Soc., 1963, 88, 2870.
21.
HaasnnotC.A.G., de LeeuwF.A.A.M., and AltonaC., Tetrahedron, 1980, 36, 2783.
22.
BreitmaierE., and VoelterW., Carbon-13 NMR Spectroscopy, 3rd edn., VCH, New York, 1990, pp. 250–254.
