Skip to main content
SpringerLink
Log in

Synthesis of 3-amino-3,4-dihydroquinazolin-4-one derivatives from anthranilic acid hydrazide and dicarboxylic acids

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Treatment of anthranilic acid hydrazide with 2 equiv of ethoxalyl chloride gave the corresponding diester which underwent cyclization in acetic anhydride to produce ethyl 3-(ethoxalylamino)-4-oxo-3,4-dihydroquinazoline-2-carboxylate. Acylation of anthranilic acid hydrazide first with succinic anhydride and then with ethoxalyl chloride led to the formation of 4-[2-(2-{[ethoxy(oxo)acetyl]amino}benzoyl)hydrazino]-4-oxobutanoic acid whose cyclization in acetic acid afforded N-(2-ethoxycarbonyl-4-oxo-3,4-dihydroquinazolin-3-yl)succinamic acid, while in acetic anhydride ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate was obtained. The latter was brought into reactions with amines and hydrazine hydrate and alkaline hydrolysis. Acylation of 2-[2-(2-aminobenzoyl)hydrazinocarbonyl]benzoic acid with ethoxalyl chloride gave ethyl N-[2-(phthalimidocarbamoyl)phenyl]oxamate, and with succinic anhydride, 3-[4-oxo-3-phthalimido-3,4-dihydroquinazolin-2-yl]propionic acid. 4-[2-(2-Aminobenzoyl)hydrazino]-4-oxobutanoic acid reacted with phthalic anhydride in boiling acetic acid to give phthalazino[1,2-b]quinazoline-5,8-dione via elimination of succinic acid residue.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Ukrainets, I.V., Taran, S.G., Gorokhova, O.V., and Bezuglyi, P.A., Khim. Geterotsikl. Soedin., 1994, p. 225.

  2. Pathak, U.S., Rathod, I.S., Patel, M.B., Shirsath, V.S., and Iain, K.S., Indian J. Chem., Sect. B, 1995, vol. 34, p. 617.

    Google Scholar 

  3. Shemchuk, L.A., Russ. J. Org. Chem., 1998, vol. 34, p. 534.

    CAS  Google Scholar 

  4. Volozhena, O.N. and Yakhontov, L.N., Khim.-Farm. Zh., 1987, vol. 16, p. 1175.

    Google Scholar 

  5. Negwer, M. and Scharnow, H.-G., Organic-Chemical Drugs and Their Synonyms, Weinheim: Wiley, 2001, 8th ed.

    Google Scholar 

  6. Dewar, M.J.S. and Thiel, W., J. Am. Chem. Soc., 1977, vol. 99, p. 4899.

    Article  CAS  Google Scholar 

  7. Atkinson, R.S. and Williams, P.J., J. Chem. Soc., Perkin Trans. 1, 1996, p. 1951.

  8. Atkinson, R.S., Coogan, M.P., and Cornell, C.L., J. Chem. Soc., Perkin Trans. 1, 1996, p. 157.

  9. Shemchuk, L.A., Chernykh, V.P., Arzumanov, P.S., Levashov, D.V., and Shemchuk, L.M., Russ. J. Org. Chem., 2007, vol. 43, p. 615.

    Article  CAS  Google Scholar 

  10. Shemchuk, L.A., Chernykh, V.P., Ivanova, I.L., Snitkovskii, E.L., Zhirov, M.V., and Turov, A.V., Russ. J. Org. Chem., 1999, vol. 35, p. 286.

    CAS  Google Scholar 

  11. Grekov, A.P. and Veselov, V.Ya., Fizicheskaya khimiya gidrazina (Physical Chemistry of Hydrazine), Kiev: Naukova Dumka, 1979, p. 26.

    Google Scholar 

  12. Reddy, G.V. and Reddy, P.S.N., Indian J. Chem., Sect. B, 1992, vol. 31, p. 764.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. National Pharmaceutical University, ul. Pushkinskaya 53, Khar’kov, 61002, Ukraine

    L. A. Shemchuk, V. P. Chernykh, P. S. Arzumanov & I. L. Starchikova

Authors
  1. L. A. Shemchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. P. Chernykh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. S. Arzumanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. L. Starchikova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © L.A. Shemchuk, V.P. Chernykh, P.S. Arzumanov, I.L. Starchikova, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 12, pp. 1827–1831.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shemchuk, L.A., Chernykh, V.P., Arzumanov, P.S. et al. Synthesis of 3-amino-3,4-dihydroquinazolin-4-one derivatives from anthranilic acid hydrazide and dicarboxylic acids. Russ J Org Chem 43, 1830–1835 (2007). https://doi.org/10.1134/S1070428007120160

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007120160

Keywords

Search

Navigation