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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 12, pp 1603–1606 | Cite as

First representative of 6b,9-epoxyisoindolo-[2,1-a]quinazoline-10-carboxylic acids

  • V. P. ZaytsevEmail author
  • F. I. Zubkov
  • E. L. Motorygina
  • M. G. Gorbacheva
  • E. V. Nikitina
  • A. V. Varlamov
Article

We have developed a synthetic route for the preparation of epoxyisoindolones condensed with various heterocycles based on the cycloaddition of unsaturated acid derivatives to α-furyl-substituted hydrogenated azaheterocycles [1]. To explore the synthetic scope of this method we have prepared the 3-alkyl-2-furyl- quinazolines 1 by the method reported in [2] and studied their reaction with maleic anhydride for the first time.

Acylation of the quinazolin-4-ones 1a-c by refluxing with maleic anhydride in toluene is accompanied by a spontaneous exo-[4 + 2] cycloaddition of an N-maleinamide fragment to the 2-furyl substituent [ 3, 4]. The epoxyisoindoloquinazoline carboxylic acids 3a-c are formed as a single diastereomer with yields from moderate to quantitative.

Keywords

2-furylquinazolin-4-ones furfurylamines isoindolo[2,1-a]quinazolines Diels-Alder reaction intramolecular [4 + 2] cycloaddition 

References

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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • V. P. Zaytsev
    • 1
    Email author
  • F. I. Zubkov
    • 1
  • E. L. Motorygina
    • 1
  • M. G. Gorbacheva
    • 1
  • E. V. Nikitina
    • 1
  • A. V. Varlamov
    • 1
  1. 1.Peoplesˈ Friendship University of RussiaMoscowRussia

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