Skip to main content
Log in

Three-Component Synthesis of Dialkyl 2-(Alkylimino-Methylene)3- (2,2,5-Trimethyl-4,6-Dioxo-1,3-Dioxan-5-Yl)-Succinates

  • Full Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Summary

The adduct produced in the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates was trapped by 2,2,5-trimethyl-1,3-dioxane-4,6-dione (methyl Meldrum's acid), to afford highly functionalized ketenimines in good yields.

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. Ugi, I. From isocyanides via four-component condensations to antibiotic syntheses, Angew. Chem. Int. Ed. Eng., 21 (1982) 810–812.

    Article  Google Scholar 

  2. Ugi, I., Lohberger, S. and Karl, R. In: Comprehensive organic synthesis, Trost, B. M. and Fleming, I. (eds) vol 2, Pergamon Oxford, (1991) 1083–1106.

  3. Domling, A. and Ugi, I., Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. Eng., 39 (2000) 3169–3210

    Google Scholar 

  4. Motoyoshiya, J., Teranishi, A., Mikoshiba, R., Yamamoto, I., Gotoh, H., Enda, J., Ohshiro, Y. and Agawa, T., C-phosphonoketenimines, characterization and synthetic application to heterocycles, J. Org. Chem., 45 (1980) 5385–5387.

    Article  CAS  Google Scholar 

  5. Cristau, H.-J., Jouanin, I. and Taillefer, M., New synthesis of diphenyl-N-(substituted)ketenimines from diaminophosphonium diazaylides, J. Organometallic Chem., 584 (1999) 68–72.

    Article  CAS  Google Scholar 

  6. Y. Ito, T. Hirao, N. Ohta and T. Saegusa, Synthesis of ketenimine via(N-alkylimino)acylpalladium complex intermediate, Tetrahedron Lett., 18 (1977) 1009–1012.

    Article  Google Scholar 

  7. Ishida, M., Minami, T. and Agawa, T., Synthetic application of methyl (phenylthio) ketene synthesis of vicinal-substituted cyclopentene derivaties, J. Org. Chem., 44 (1979) 2067–2072.

    Article  CAS  Google Scholar 

  8. Getzmann, R., Moller, M. H., Rodewald, U., Frohlich, R., Grehl, M. and Wurthwein, E.U., Metallated ketenimines: Deprotonation of n-isopropyl-diphenyl-ketenimine and subsequent trapping reaction with electrophiles. A theoretical and experimental study. Tetrahedron, 51 (1995) 3767–3786.

    Article  Google Scholar 

  9. (a) Yavari, I., Davar-Panah, M., Heydari, M., Najafian, K. and Zonouzi, A. A facil route to highly functionalized ketenimines, Monatsh. Chem., 127 (1996) 963–966; (b) I. Yavari, I. and Nourmohammadian, F. A simple synthesis of highly functionalized ketenimines, J. Chem. Res., (S) (2000) 218–219; (c) Yavari, I., Djahaniani, H. and Nassiri, F. Coll. Czech. Chem. Commun., 69 (2004) 1499–1507; (d) Yavari, I., Djahaniani, H. and Nassiri, F.A simple synthesis of highly functionalized 1-azabutadienes and ketenimines, Monatsh. Chem., 135 (2004) 543–548; (e) Yavari, I., Nassiri, F. and Djahaniani, H. Synthesis and dynamic NMR study of ketenimines derived from tert-butyl isocyanide, alkyl 2-arylamino-2-oxo-acetates, and dialkyl acetylenedicarboxylates, Mol. Diversity, 8 (2004) 431–435; (f) Yavari, I., Nori-Shargh, D., and Fallah-Bagher-Shaidaii, H. Reaction of Meldrum's acid with alkyl isocyanides. synthesis of a novel class of furan derivatives, J. Chem. Res., (S) (1996) 146–147.

  10. Nair, V. J., Rajesh, C., Vinod, A. U., Bindu, S., Sreekanth, A. R., Mathess, J. S. and Balagopal, L. Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes, Acc. Chem. Res., 36 (2003) 899–909.

    Article  CAS  Google Scholar 

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., Zare, H. & Mohtat, B. Three-Component Synthesis of Dialkyl 2-(Alkylimino-Methylene)3- (2,2,5-Trimethyl-4,6-Dioxo-1,3-Dioxan-5-Yl)-Succinates. Mol Divers 10, 247–250 (2006). https://doi.org/10.1007/s11030-005-9010-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-005-9010-4

Key words

Navigation