Skip to main content

Introducing a novel class of four-component reactions

Molecular Diversity volume 6, pages 199–206 (2003)Cite this article

Abstract

A novel four-component reaction approach to the efficient synthesis of triamide and amidodiester derivatives using amines or alcohols, aldehydes and alkyl or aryl isocyanides in the presence of Meldrum's acid as a CH acid, instead of carboxylic acid of Ugi four-component reaction, was studied.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

References

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

    Article  Google Scholar 

  2. Ugi, I., Lohberger, S. and Karl, R., in Comprehensive of organic synthesis; Trost, B. M., Fleming, I. and Heathcock, C. H., Eds., Pergamon: New York, 1991; Vol. 2, pp 1083-1109.

    Google Scholar 

  3. Ugi, I., The ?-addition of immonium ions and anions to isonitriles accompanied by secondary reactions, Angew. Chem. Int. Ed. Engl., 1 (1962) 8-21.

    Article  Google Scholar 

  4. Keating, T. A. and Armstrong, R. W., The Ugi five-component condensation using CO2, CS2 and COS as oxidized carbon sources, J. Org. Chem., 63 (1998) 867-871.

    Article  CAS  Google Scholar 

  5. Shaabani, A., Teimouri, M. B. and Bijanzadeh, H. R., One-pot three component condensation reaction in water: An efficient and improved procedure for the synthesis of furo[2,3-d]pyrimidine-2,4(1H,3H)-diones, Tetrahedron Lett., 43 (2002) 9151-9154.

    Article  CAS  Google Scholar 

  6. Shaabani, A. and Teimouri, M. B., The reaction of alkyl isocyanides and benzylidene Meldrum's acid drivatives in the presence of water: A one-pot synthesis of 4-(alkylamino)-3-aryl-4-oxobutanoic acids, J. Chem. Research(S), (2002) 433-435.

  7. Shaabani, A., Teimouri, M. B. and Bijanzadeh, H. R., The reaction of alkyl isocyanides and dialkylacetylene dicarboxylates with phthalic anhydride derivatives: A novel synthesis of ?-spiroiminolactones, J. Chem. Research(S), (2002) 381-383.

  8. Shaabani, A., Bazgir, A., Soleimani, K. and Bijanzadeh, H. R., Reaction between alkyl isocyanides and 1,1,1,5,5,5-hexafluoropentane-2,4-dione in the presence of water: Onepot synthesis of highly fluorinated ?-dihydroxy-?-hydroxy amides and ?-keto-?-hydroxy amides, J. Flourine Chem., 116 (2002) 93-95.

    Article  CAS  Google Scholar 

  9. Shaabani, A., Yavari, I., Teimouri, M. B., Bazgir, A. and Bijanzadeh, H. R., New and efficient synthesis of dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)-2-oxoethyl]malonates, Tetrahedron, 57 (2001) 1375-1378.

    Article  CAS  Google Scholar 

  10. Shaabani, A., Ajabi, S., Farrokhzad, F. and Bijanzadeh, H. R., [1+4] Cycloaddition of isocyanides with 2-acetyl-1,4-benzoquinone; A conveient synthesis of isobenzofuran-4,7-quinones, J. Chem. Research(S), (1999) 582-583.

  11. Yavari, I., Shaabani, A. and Maghsoodlou, M. T., On the reaction between alkyl isocyanides and 3-benzylidene-2,4-pentanedione. A convenient synthetic route to densely functionalized furanes, Monatsh. Chem., 128 (1997) 697-700.

    Article  CAS  Google Scholar 

  12. Shaabani, A. and Farrokhzad, F., [1 + 4] Cycloaddition of isocyanides with 3-(1-hydroxyethylidene)pentane-2,4-dione. A convenient synthesis of iminolactones, J. Chem. Research(S), (1997) 344.

  13. McNab, H., Meldrum's acid, Chem. Soc. Rev., 7 (1978) 345-358.

    Article  CAS  Google Scholar 

  14. Bigi, F., Carloni, S., Ferrari, L., Maggi, R., Mazzacani, A. and Sartori, G., Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes, Tetrahedron Lett., 42 (2001) 5203-5205.

    Article  CAS  Google Scholar 

  15. Tietze, L. F. and Beifuss, U. W. E., in 'Comprehensive Organic Synthesis', Trost, B. M., Fleming, I., Heathcock, C. H., eds., Pergamon Press: Oxford, 2 (1991) 341-394.

    Google Scholar 

  16. Marchand, E., Morel, G. and Sinbandhit, S., A new access to 2-(alkylamino)-and 2-(arylamino)pyrroles by addition of isocyanides to protonated 1-azabutadienes, Eur. J. Org. Chem., (1999) 1729-1738.

  17. Morel, G., Marchand, E., Sinbandhit, S. and Carlier, R., á-Thioxothioamides: a formal [1 + 4] cycloaddition reaction with isocyanides and diisocyanides and its application to a new straightforward formation of extended tetrathiofulvalenes, Eur. J. Org. Chem., (2001) 655-662.

  18. Nair, V., Menon, R. S., Vinod, A. U. and Viji, S., A facile three-component reaction involving [1 + 4] cycloaddition leading to furan annulated heterocycles, Tetrahedron Lett., 43 (2002) 2293-2295.

    Article  CAS  Google Scholar 

  19. Figueroa-Villar, J. D., Carneiro, C. L., Cruz, E. R., Synthesis of 6-phenylaminofuro[2,3-d]pyrimidine-2,4(1H,3H)-diones from barbiturylbenzylidens and isonitriles, Heterocycles, 34 (1992) 891-893.

    Article  CAS  Google Scholar 

  20. Oikawa, Y., Sugano, K., and Yonemitsu, O., Meldrum's acid in organic synthsis. 2. A general and versatile synthesis of ?-ketoesters, J. Org. Chem., 43 (1978) 2087-2088.

    Article  CAS  Google Scholar 

  21. Oikawa, Y., Hirasawa, H. and Yonemitsu, O., Meldrum's acid in organic synthesis. 1. A convenient one-pot synthesis of ethyl indolepropionates, Tetrahedron Lett., 19 (1978) 1759-1762.

    Article  Google Scholar 

  22. Chen, B.-C., Meldrum's acid in organic synthesis, Heterocycles, 32 (1991) 529-597.

    CAS  Google Scholar 

  23. Davidson, D. and Bernhard, S. A., The structure of Meldrum's supposed ?-lactonic acid, J. Am. Chem. Soc., 70 (1948) 3426-3428.

    CAS  Google Scholar 

  24. Corey, E. J., The mechanism of decarboxylation of ?, ?-and ?, ?-unsaturated malonic acid derivatives and the course of decarboxylative condensation reactions in pyridine, J. Am. Chem. Soc., 74 (1952) 5897-5905.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Shahid Beheshti University, Zip Code 1983963113, Tehran, Iran

    Ahmad Shaabani

  2. Department of Chemistry, Shahid Beheshti University, Zip Code 1983963113, Tehran, Iran

    Mohammad Bagher Teimouri & Ayoob Bazgir

  3. Department of Chemistry, Tarbiat Modarres University, P. O. Box 14155, 4838, Tehran, Iran

    Hamid Reza Bijanzadeh

Authors
  1. Ahmad Shaabani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Bagher Teimouri
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ayoob Bazgir
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hamid Reza Bijanzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ahmad Shaabani.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Shaabani, A., Teimouri, M.B., Bazgir, A. et al. Introducing a novel class of four-component reactions. Mol Divers 6, 199–206 (2003). https://doi.org/10.1023/B:MODI.0000006759.20910.f1

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:MODI.0000006759.20910.f1

  • alcohol
  • amidodiester
  • amine
  • isocyanide
  • Meldrum's acid
  • triamide