Synthesis of New Fused Thieno[3,2-d]pyrimidine Derivatives Based on 4-(Furan-2-yl)-7,7-dimethyl-2-sulfanyl-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile
Methods of synthesis of new fused thieno[3,2-e]pyridines and thieno[3,2-d]pyrimidines have been developed. 4-(Furan-2-yl)-7,7-dimethyl-2-sulfanyl-7,8-dihydro-5H-pyrano[4,3-b]pyridine-3-carbonitrile has been found to react with 2-chloroacetamides in two directions, depending on the temperature. The reaction at elevated temperature (60–65°C) involved alkylation followed by intramolecular cyclization with the formation of pyrano[4,3-b]thieno[3,2-e]pyridine derivatives, whereas at room temperature, the corresponding 2-sulfanylacetamides were obtained. The condensation of pyrano[4,3-b]thieno[3,2-e]pyridine-2-carboxamides with triethyl orthoformate afforded new fused tetracyclic thieno[3,2-d]pyrimidine derivatives.
Authors
- Sh. Sh. Dashyan (ORCID: https://orcid.org/0000-0002-6365-3725)
- M. R. Baghdasaryan (ORCID: https://orcid.org/0000-0001-7092-0556)
- I. M. Barkhudaryants (ORCID: https://orcid.org/0000-0002-4620-6034)
- V. V. Dabayeva (ORCID: https://orcid.org/0000-0003-2980-2552)
- E. G. Paronikyan (ORCID: https://orcid.org/0000-0002-6048-3599)
Institutions
- Institute of Fine Organic Chemistry of Scientific - Technological Center of Organic and Pharmaceutical Chemistry (AM)
- National Academy of Sciences of Armenia (AM)
Publication Details
- Journal
- Russian Journal of Organic Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1134/s1070428025601025
- Primary Topic
- Synthesis and biological activity
- Type
- article
- Field-Weighted Citation Impact
- 0.00