Synthesis of New Condensed Derivatives of Thieno[3,2- d ]-pyrimidines Based on 7,7-Dimethyl-2-mercapto-4-(2-furyl)-3-cyano-7,8-dihydro-5 H -pyrano[4,3- b ]pyridine

V. V. Dabaeva; Дабаева В. В.; I. M. Barkhudaryants; Бархударянц И. М.; E. G. Paronikyan; Пароникян Е. Г.; Sh. Sh. Dashyan; Дашян Ш. Ш.; M. R. Baghdasaryan; Багдасарян М. Р.

doi:10.31857/S0514749225010086

Synthesis of New Condensed Derivatives of Thieno[3,2-d]-pyrimidines Based on 7,7-Dimethyl-2-mercapto-4-(2-furyl)-3-cyano-7,8-dihydro-5H-pyrano[4,3-b]pyridine

Authors: Dabaeva V.V.¹, Barkhudaryants I.M.¹, Paronikyan E.G.¹, Dashyan S.S.¹, Baghdasaryan M.R.¹
Affiliations:
1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
Issue: Vol 61, No 1 (2025)
Pages: 102-108
Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://rjmseer.com/0514-7492/article/view/682063
DOI: https://doi.org/10.31857/S0514749225010086
EDN: https://elibrary.ru/AFKMTG
ID: 682063

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription or Fee Access

Abstract

Methods for the synthesis of new condensed thieno[3,2-e]pyridines and thieno[3,2-d]pyrimidines have been developed. The reaction of 7,7-dimethyl-2-mercapto-4-(2-furyl)-3-cyano-7,8-dihydro-5H-pyrano[4,3-b]pyridine with chloroacetic acid amides has been established depending on temperature. It has been shown that at high temperatures alkylation and intramolecular cyclization (one pot reaction) occur with the formation of pyrano[4,3-b]thieno[3,2-e]pyridines. New derivatives of condensed tetracyclic thieno[3,2-d]pyrimidines were synthesized by condensation of pyrano[4,3-b]thieno[3,2-e]pyridine carboxamides with orthoformic acid triethyl ester.

Keywords

alkylation, one pot reaction, thieno[3,2-е]pyridine, thieno[3,2-d]pyrimidine

Full Text

References

Chiacchio M. A., Iannazzo D., Romeo R., Giofrè S. V., Legnani, L. Curr. Med. Chem., 2019, 26 (40), 7166–7195. doi: 10.2174/0929867325666180904125400
El‐Mekabaty A., Fouda A.E.A.S., Shaaban I.E. J. Heterocycl. Chem., 2020, 57 (7), 2928–2935. doi: 10.1002/jhet.4002
Zaki R.M., Kamal El-Dean A.M., Radwan S.M., Ammar M.A. Russ. J. Bioorg. Chem., 2022, 48 (Suppl 1), S121–S135. doi: 10.1134/S1068162023010314
Alenazi N.A., Alharbi H., Qarah A.F., Alsoliemy A., Abualnaja M.M., Karkashan A., Abbas B., El-Metwaly N.M. Arab. J. Chem., 2023, 16 (11), 105226. doi: 10.1016/j.arabjc.2023.105226
Mohi El-Deen E.M., El-Gwaad A., Amina A., Anwar M.M. Egypt. J. Chem., 2023, 66 (2), 231–242. doi: 10.21608/EJCHEM.2022.136967.6042
Saber A.F., Kamal El‐Dean A.M., Redwan S.M., Zaki R.M. J. Chinese Chem. Soc., 2020, 67 (7), 1239–1246. doi: 10.1002/jccs.201900374
Binsaleh N.K., Wigley C.A., Whitehead K.A., van Rensburg M., Reynisson J., Pilkington L.I., Barker D., Jones S., Dempsey-Hibbert N.C. Eur. J. Med. Chem., 2018, 143, 1997–2004. doi: 10.1016/j.ejmech.2017.11.014
Liu Y.F., Fu S.Q., Yan Y.C., Gong B.B., Xie W.J., Yang X.R., Sun T., Ma M. Drug Des. Devel. Ther. 2021, 15, 639–649. doi: 10.2147/DDDT.S291369
Sarker D., Ang J.E., Baird R., Kristeleit R., Shah K., Moreno V., Clarke P.A., Raynaud F.I., Levy G., Ware J.A., Mazina K., Lin R., Wu J., Fredrickson J., Spoerke J.M., Lackner M.R., Yan Y., Friedman L.S., Kaye S.B., Derynck M.K., Workman P., de Bonoet J.S. Clin. Cancer Res. 2015, 21, 77–86. doi: 10.1158/1078-0432.CCR-14-0947
Kim D.W., Lee D.H., Han J.Y., Lee J., Cho B.C., Kang J.H., Lee K. H., Cho E. K., Kim J.-S., Min Y. J., Cho J.Y., An H.J., Kim H.-G., Lee K.H., Kim B.-S., Jang I.-J., Yoon S., Han O.P., Noh Y.S., Hong K.Y., Park K. Lung Cancer. 2019, 135, 66–72. doi: 10.1016/j.lungcan.2019.07.007
Дабаева В.В., Багдасарян М.Р., Бархударянц И.М., Пароникян Е.Г., Паносян Г.А., Дашян Ш.Ш. ЖОХ, 2022, 92 (9), 1442–1448. [Dabaeva V.V., Bagdasaryan M.R., Barkhudaryants I.M., Paronikyan E.G., Panosyan G.A., Dashyan Sh.Sh. Russ. J. Gen. Chem., 2022, 92, 1686–1691. doi: 10.1134/S1070363222090109]