Synthesis of 8-alkylthio- and 8-selanyl-3-tert-butylpyrazolo[5,1-c][1,2,4]triazines

Synthesis of 8-alkylthio- and 8-selanyl-3-tert-butylpyrazolo[5,1-c][1,2,4]triazines Full article

Journal

Phosphorus, Sulfur and Silicon and the Related Elements
ISSN: 1042-6507 , E-ISSN: 1563-5325

Output data

Year: 2020, Volume: 195, Number: 8, Pages: 666-676 Pages count : 11 DOI: 10.1080/10426507.2020.1712395

Authors

Ivanov Sergey M. ^1,2 , Mironovich Lyudmila M. ³ , Minyaev Mikhail E. ¹

Affiliations

1	Laboratory of Medicinal Chemistry, N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Moscow, Russia;
2	Skoltech Department, D.I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia;
3	Southwest State University, Kursk, Russia

Interaction of 8-lithio-3-tert-butyl-4-oxopyrazolo[5,1-c][1,2,4]triazin-1-ide with elemental sulfur or selenium in THF with further in situ alkylation at –97 °C followed by warming to room temperature furnished a series of 3-tert-butyl-8-X-pyrazolo[5,1-c][1,2,4]triazin-4(6H)-ones (X = n-BuS, n-BuSe, MeSe, PhCH2S) in good yields. 8,8'-Diselanediylbis(3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(1H)-one) was also isolated as a by-product in these reactions. One-pot interaction of the n-BuSe substituted derivative with diborane/boron trifluoride led to reduction of the 1,2,4-triazine core and partial elimination of the alkylselanyl moiety. The structures of the synthesized products were established on the basis of IR, 1H, 13C, 2D HMBC 1H–77Se NMR and high resolution mass spectra, as well as X-ray single crystal diffraction analyses. Two of the prepared compounds were also tested for antimicrobial and antifungal activities.

Ivanov S.M. , Mironovich L.M. , Minyaev M.E.
Synthesis of 8-alkylthio- and 8-selanyl-3-tert-butylpyrazolo[5,1-c][1,2,4]triazines
Phosphorus, Sulfur and Silicon and the Related Elements. 2020. V.195. N8. P.666-676. DOI: 10.1080/10426507.2020.1712395 WOS Scopus OpenAlex

≡ Web of science:	WOS:000506730000001
≡ Scopus:	2-s2.0-85078603623
≡ OpenAlex:	W2998982796