Chemistry of Heterocyclic Compounds

, Volume 43, Issue 10, pp 1301–1306 | Cite as

Derivatives of arborine [1-methyl-2-(phenylmethyl)-4(1H)-quinazolinone]

  • V. A. KovtunenkoEmail author
  • T. T. Kucherenko
  • R. I. Zubatyuk
  • O. V. Shishkin
  • D. A. Yushchenko


A method has been developed for the reaction of 2-cyanomethylbenzoic acid with N-methylanthranilic acid to give 2-[(1-methyl-4-oxo-1,4-dihydro-2-quinazolin-2-yl)methyl]benzoic acid, its esters were synthesized. The spectroscopic chracteristics of the isomeric compounds have been studied and compared in solution and in the solid state.


2-methylaminobenzoic acid 2-cyanomethylbenzoic acid 2-[(1-methyl-4-oxo-1,3-dihydroquinazolin-2-yl)methyl]benzoic acid X-ray structural analysis 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    D. Chakravarti, R. N. Chakravarti, L. A. Cohen, B. Dasgupta, S. Datta, and H. K. Miller, Tetrahedron, 16, 224 (1961).CrossRefGoogle Scholar
  2. 2.
    J. Mathukrishnan, K.-H. Seifert, K. H. Hoffmann, and M. W. Lorenz, Phytochemistry, 50, 249 (1999).CrossRefGoogle Scholar
  3. 3.
    K. H. Hauptmann, Arzneim. Forsch., 15, 610 (1965).Google Scholar
  4. 4.
    V. A. Kovtunenko, T. T. Kucherenko, O. V. Shishkin, and V. M. Kisel, Khim. Geterotsikl. Soedin., 1408 (2002). [Chem. Heterocycl. Comp., 38, 1242 (2002)].Google Scholar
  5. 5.
    Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 58, 713 (1989).Google Scholar
  6. 6.
    O. V. Shishkin, Monatsh. Chem., 127, 883 (1996).CrossRefGoogle Scholar
  7. 7.
    O. V. Shishkin and A. S. Polyakova, Izv. Akad. Nauk, Ser. Khim., 1938 (1996).Google Scholar
  8. 8.
    M. T. Bogert and R. Seil, J. Am. Chem. Soc., 29, 517 (1907).CrossRefGoogle Scholar
  9. 9.
    J. S. Aggarwal, R. S. Das, and J. N. N. Ray, J. Indian Chem. Soc., 6, 717 (1929); Chem. Abstr., 24, 1113 (1930).Google Scholar
  10. 10.
    H. Manabe and O. Hiroshi, Chem. Pharm. Bull., 41, 1114 (1993).Google Scholar
  11. 11.
    A. R. Katritzky, Physical Methods in Heterocyclic Chemistry, Academic Press, New York (1963), p. 161.Google Scholar
  12. 12.
    L. J. Bellamy, New Data on the IR Spectra of Complex Molecules [Russian translation], Mir, Moscow (1971), p. 175.Google Scholar
  13. 13.
    G. M. Sheldrick, SHELXTL PLUS PC Version. A System of Computer Programs for the Determination of Crystal Structures from X-ray Diffraction Data, Rev. 5.1 (1998).Google Scholar
  14. 14.
    G. Price and R. Rogers, Syntheses of Organic Preparations [Russian translation], Vol. 3, Inostr. Lit. Moscow (1952), p. 267.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • V. A. Kovtunenko
    • 1
    Email author
  • T. T. Kucherenko
    • 1
  • R. I. Zubatyuk
    • 2
  • O. V. Shishkin
    • 2
  • D. A. Yushchenko
    • 1
  1. 1.Taras Shevchenko National UniversityKievUkraine
  2. 2.STC “Institute for Single Crystals”Ukraine National Academy of SciencesKharkiv

Personalised recommendations