Skip to main content
Log in

Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea

  • Full-length paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

The stabilized phosphoranes, obtained from the three-component reaction between dialkyl acetylenedicarboxylates and urea or N-methylurea in the presence of triphenylphosphine, undergo a smooth reaction in boiling toluene to produce iminophosphoranes in good yields. Under the same reaction conditions, the phosphorane obtained from N-methylurea and dimethyl acetylenedicarboxylate yields methyl 1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Dömling, A. and Ugi, I., Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. Eng., 39 (2000) 3168–3210.

    Google Scholar 

  2. (a) Huisgen, R., Century lecture 1,3-dipolar cycloadditions, Proc. Chem. Soc., (1961) 357–369; (b) Winterfeldt, E., Additions to the activated CC triple bonds, Angew. Chem. Int. Ed. Eng., 6 (1967) 423–434.

  3. (a) Johnson, A.W. and Tebby, J.C., The adducts from triphenylphosphine and dimethyl acetylenedicarboxylate, J. Chem. Soc., (1961) 2126–2130; (b) Tebby, J.C., Wilson, I.F. and Grifiths D.V., Reactions of phosphines with acetylenes. Part 18. The mechanism of formation of 1,2-alkylidene phosphoranes, J. Chem. Soc., Perkin Trans. 1, (1979) 2133–2135.

    Google Scholar 

  4. (a) Johnson, A.W., Ylides and imines of phosphorus, Wiley: New York, 1993; (b) Corbrige, D.E.C., Phosphorus. An outline of chemistry, biochemistry and technology; 5th Edn., Elsevier: Amsterdam, 1995; (c) Nicolaou, K.C., Harter, M.W., Gunzner, J.L. and Nadin, A., The Wittig and related reactions in natural product synthesis, Liebigs Ann. (1997) 1283–1288; (d) Cherkasov, R.A. and Pudovik, M.A., Heterophosphacyclanes in organic synthesis, Russ. Chem. Rev., 63 (1994) 1019–1045; (e) Maryanoff, B.E. and Reitz, A.B., The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects, Chem. Rev., 89 (1989) 863–927.

  5. (a) Yavari, I. and Adib, M., Efficient synthesis of 5,6,7-trisubstituted 1H-pyrrolizines, Tetrahedron 57 (2001) 5873–5878; (b) Yavari, I., Adib, M., Jahani-Moghaddam, F. and Bijanzadeh, H.R., Vinylphosphonium salt mediated simple synthesis of 7-oxo-7H- pyrido[1,2,3-cd]perimidine derivatives, Tetrahedron 58 (2002) 6901–6906; (c) Yavari, I., Bayat, M., Maghsoodlou, M.T. and Hazeri, N., A simple synthesis of stable phosphoranes derived from imides or acetanilide derivatives, Phosph. Sulf. Silic., 177 (2002) 2599–2610; (d) Yavari, I., M. Adib, M. and L. Hojabri, L., Vinyltriphenylphosphonium salt mediated serendipitous synthesis of aryliminophosphoranes, Tetrahedron, 58 (2002) 7213–7219; (e) Yavari, I. and Zabarjad-Shiraz, N., Triphenylphosphine mediated efficient synthesis of 4-substituted-1- methyl-2,5-dioxo-3-imidazolines, Monatsh. Chem., 134 (2003) 445–451; (f) Yavari, I., Adib, M., Abdolmohammadi, Sh. and Aghazadeh, M., Synthesis and dynamic NMR spectroscopic study of dialkyl 4-ethoxy-1-(1-naphthyl)-5-oxo-4,5-dihydro-1H- pyrrole-2,3-dicarboxylates, Monatsh. Chem., 134 (2003) 1093–1098; (g) Yavari, I., Alizadeh, A. and Mohebbi, H., Addition-reduction reaction between trimethyl phosphite and dibenzoylacetylene in the presence of SH- or NH-acids, Phosph. Sulf. Silic., 178 (2003) 1741–1746; (h) Yavari, I., Alizadeh, A. and Anari-Abbasinejad, M., An efficient synthesis of stable sulfur-containing phosphoranes derived from 1-methylimidazole-2-thiol, Phosph. Sulf. Silic., 178 (2003) 269–277; (i) Yavari, I. and Zabarjad-Shiraz, N., Triphenylphosphine mediated chemoselective synthesis of functionalized spiro-imidazol-4-ones, Phosph. Sulf. Silic., 179 (2004) 1477–1481; (j) Yavari, I. and Zabarjad-Shiraz, N., Synthesis of sulfur-containing aryliminophosphoranes, Phosph Sulf. Silic., 179 (2004) 1381–1386.

  6. (a) Horner, L. and Gross, A., Use of phosphineimines in causing the introducing of primary amino groups, Liebigs Ann., 591 (1955) 117–134; (b) Norris, W.P. and Henrry, R.A., Cyanoguanyl azide chemistry, J. Org. Chem., 29 (1964) 650–660.

  7. (a) Bachster, M., Alkyl derivatives of orotic acid, Ber., 64 B (1931) 2683–2685; (b) Curran, W. V. and Angier R., The synthesis of orotidine and its isomer, 3-β -D-ribofuranosylorotic acid, and the methylation of orotic acid, J. Org. Chem., 31 (1966) 201–205.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Issa Yavari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yavari, I., Zabarjad-Shiraz, N. Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea. Mol Divers 10, 23–27 (2006). https://doi.org/10.1007/s11030-006-8696-2

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-006-8696-2

Keywords

Navigation