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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 7, pp 1108–1110 | Cite as

Unusual transformations of anthranilic acid imidazolides

  • M. S. Baranov
  • I. V. Yampolsky
Article

Carbonyldiimidazole (CDI) is widely used as a reagent for the activation of a carboxyl group [1, 2]. It readily converts acids into the corresponding imidazolides, which can yield amides or esters upon the action of amines or alcohols, respectively. Methods for carrying out such reactions are well developed, and side reactions are rarely encountered [3].

However, in the course of our work, we have revealed an interesting feature in the behavior of anthranilic acid imidazolides. Prolonged heating of the acids 1a,b with CDI in dioxane gives compounds 3a,b as the main products.

The structures of compounds 3a, b were established by 1D 1H NMR and 13C NMR spectroscopy. In case of compound 3b, it was additionally confirmed with 2D COSY, 13C-HSQC, 15N-HSQC, and 15N-HMBC spectra, as well as by X-ray analysis (Fig.  1).

Keywords

anthranilic acid carbonyldiimidazole imidazolides acid activation acylation 

Notes

The authors thank the Russian Foundation for Basic Research (grant 11-4-01293-a) for financial support.

References

  1. 1.
    R. C. Morton, D. Mangroo, and G. E. Gerber, Can. J. Chem., 66, 1701 (1988).CrossRefGoogle Scholar
  2. 2.
    R. Paul and G. W. Anderson, J. Am. Chem. Soc., 82, 4596 (1960).CrossRefGoogle Scholar
  3. 3.
    A. Armstrong, N,N'-Carbonyldiimidazole, in: Encyclopedia of Reagents for Organic Synthesis, J. Wiley & Sons, New York (2001).Google Scholar
  4. 4.
    D. C. Palmer, Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A, Vol. 60, Chemistry of Heterocyclic Compounds: A Series of Monographs, J. Wiley & Sons, New York (2003), p. 183.CrossRefGoogle Scholar
  5. 5.
    M. R. Grimmett, Adv. Het. Chem., 12, 103 (1970).CrossRefGoogle Scholar
  6. 6.
    G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).Google Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  1. 1.M. M. Shemyakin-Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of SciencesMoscowRussia

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