Skip to main content
SpringerLink
Log in

Azines and azoles: CXXIII. Three-component condensation of 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione with o-phenylenediamine and carbonyl compounds as a convenient synthesis of substituted 1,5-benzodiazepines

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

Abstract

Readily accessible 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione reacted with an equimolar amount of o-phenylenediamine under mild conditions (propan-2-ol, 5 min, reflux) to give the corresponding Schiff base. Reactions of the latter with aldehydes and ketones in propan-1-ol in the presence of a catalytic amount of trifluoroacetic acid or in acetic acid led to the formation of 4-hydroxy-5-(2-R-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-2H-1,3-thiazine-2,6-diones.

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. Yuskovets, V.N., Moskvin, A.V., Mikhailov, L.E., and Ivin, B.A., Zh. Obshch. Khim., 2005, vol. 75, no. 1, p. 146.

    Google Scholar 

  2. Yuskovets, V.N. and Ivin, B.A., Tetrahedron Lett., 2003, vol. 44, p. 5279.

    Article  CAS  Google Scholar 

  3. Yuskovets, V.N., Moskvin, A.V., and Ivin, B.A., Russ. J. Gen. Chem., 2004, vol. 74, no. 2, p. 312.

    Article  CAS  Google Scholar 

  4. Lloyd, D. and McNab, H., Adv. Heterocycl. Chem., 1998, vol. 71, p. 1.

    Article  CAS  Google Scholar 

  5. Chimirri, A., Gitto, R., Grasso, S., Monforte, A.M., Romeo, G., and Zappala, M., Heterocycles, 1993, vol. 36, p. 601.

    CAS  Google Scholar 

  6. Chimirri, A., Gitto, R., Grasso, S., Monforte, A.M., Romeo, G., and Zappala, M., Heterocycles, 1993, vol. 36, p. 865.

    CAS  Google Scholar 

  7. Solomko, Z.F. and Kost, A.N., Chem. Heterocycl. Comp., 1975, p. 1231.

  8. Roman, G., Comanita, E., and Comanita, B., Acta Chim. Slov., 2002, vol. 49, p. 575.

    CAS  Google Scholar 

  9. Ait-Baziz, N., Rachedi, Y., Hamdi, M., Silva, A.M.C., Balegroune, F., Thierry, R., and Sellier, N., J. Heterocycl. Chem., 2004, vol. 41, p. 587.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Chemical and Pharmaceutical Academy, ul. Professora Popova 14, St. Petersburg, 197376, Russia

    V. N. Yuskovets, Berzhe Uankpo & B. A. Ivin

Authors
  1. V. N. Yuskovets
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Berzhe Uankpo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. A. Ivin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © V.N. Yuskovets, Berzhe Uankpo, B.A. Ivin, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 5, pp. 839–849.

For communication CXXII, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yuskovets, V.N., Uankpo, B. & Ivin, B.A. Azines and azoles: CXXIII. Three-component condensation of 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione with o-phenylenediamine and carbonyl compounds as a convenient synthesis of substituted 1,5-benzodiazepines. Russ J Gen Chem 76, 801–813 (2006). https://doi.org/10.1134/S1070363206050240

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363206050240

Keywords

Search

Navigation