Skip to main content
SpringerLink
Log in

Synthesis of Substituted Thienopyrimidinones Based on Ethyl 2-Amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate

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

Abstract

Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3-d]pyrimidin-4(1H)-ones by the action of hydrazine hydrate. The con­densation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-amino­thienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.

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

Scheme
Scheme
Scheme

REFERENCES

  1. The Use of Stems in the Selection of International Non­proprietary Names (INN) for Pharmaceutical Substances, Geneva, WHO, 2018.

  2. Giri, R.S., Thaker, H.M., Giordano, T., Williams, J., Rogers, D., Vasu, K.K., and Sudarsanam, V., Bioorg. Med. Chem., 2010, vol. 18, p. 2796. https://doi.org/10.1016/j.bmc.2010.01.007

    Article  CAS  PubMed  Google Scholar 

  3. Tang, J., Huber, A.D., Pineda, D.L., Boschert, K.N., Wolf, J.J., Kankanala, J., Xie, J., Sarafianos, S.G., and Wang, Zh., Eur. J. Med. Chem., 2019, vol. 164, p. 179. https://doi.org/10.1016/j.ejmech.2018.12.047

    Article  CAS  PubMed  Google Scholar 

  4. Jin, X., Merrett, J., Tong, Sh., Flower, B., Xie, J., Yu, R., Tian, Sh., Gao, L., Zhao, J., Wang, X., Jiang, T., and Proud, Ch.G., Eur. J. Med. Chem., 2019, vol. 162, p. 735. https://doi.org/10.1016/j.ejmech.2018.10.070

    Article  CAS  PubMed  Google Scholar 

  5. Vardanyan, S.O., Aghekyan, A.A., Avagyan, A.S., Harutyunyan, S.A., and Gasparyan, H.V., Russ. J. Org. Chem., 2019, vol. 55, p. 598. https://doi.org/10.1134/S1070428019050038

    Article  CAS  Google Scholar 

  6. Arutyunyan, S.A., Vestn. Mezhdunar. Akad. Nauk Ekol. Bezop. Zhiznedeyat., 2005, vol. 10, p. 169.

    Google Scholar 

Download references

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

Author information

Authors and Affiliations

  1. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 0014, Yerevan, Armenia

    S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, S. A. Harutyunyan, H. V. Gasparyan & A. A. Aghekyan

Authors
  1. S. O. Vardanyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Avagyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. B. Sargsyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. A. Harutyunyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. H. V. Gasparyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. A. Aghekyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. S. Avagyan.

Ethics declarations

ETHICS APPROVAL AND CONSENT TO PARTICIPATE

This work was carried out in compliance with all applicable international, national and institutional guidelines for the care and use of animals.

CONFLICT OF INTEREST

The authors declare that they have no conflicts of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vardanyan, S.O., Avagyan, A.S., Sargsyan, A.B. et al. Synthesis of Substituted Thienopyrimidinones Based on Ethyl 2-Amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate. Russ J Org Chem 60, 397–402 (2024). https://doi.org/10.1134/S1070428024030047

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428024030047

Keywords:

Search

Navigation