Abstract
Selective thiocyanation (yield 70–90%) at the 3-position of pyrazolo[1,5-a]pyrimidines was performed with thiocyanogen electrochemically generated in situ from NH4SCN in MeCN on a Pt anode. For substrates with higher oxidation potential addition of Lewis acids was necessary.
References
1.
Petrosyan V.A.
Mendeleev Communications,
2011
2.
Shchepochkin A.V., Chupakhin O.N., Charushin V.N., Petrosyan V.A.
Russian Chemical Reviews,
2013
3.
10.1016/j.mencom.2016.09.016_bib0015
Ingold
Structure and Mechanism in Organic Chemistry,
1969
4.
Kokorekin V.A., Sigacheva V.L., Petrosyan V.A.
Tetrahedron Letters,
2014
5.
6.
Nagamachi T., Fourrey J.L., Torrence P.F., Waters J.A., Witkop B.
Journal of Medicinal Chemistry,
1974
7.
Elhalem E., Bailey B.N., Docampo R., Ujváry I., Szajnman S.H., Rodriguez J.B.
Journal of Medicinal Chemistry,
2002
8.
V. A. Kokorekin, G.V. Ramenskaya, G.M. Rodionova and V. A. Petrosyan, in Proceedings of IV International Scientific-practical Conference ‘High Technologies, Basic and Applied Researches in Physiology and Medicine’, St. Petersburg, Russia, 2012, vol. 1. p. 40 (in Russian).
9.
Kokorekin V.A., Terent’ev A.O., Ramenskaya G.V., Grammatikova N.É., Rodionova G.M., Ilovaiskii A.I.
Pharmaceutical Chemistry Journal,
2013
10.
10.1016/j.mencom.2016.09.016_bib0050
Wood
1946
11.
10.1016/j.mencom.2016.09.016_bib0055
Guy
1977
12.
10.1016/j.mencom.2016.09.016_bib0060
Nikoofar
Chem. Sci. Trans.,
2013
13.
K. E. Rosner, J. Popovici-Muller, Y. Deng, T. Wang and P. J. Curran, US Patent 7196111 B2, 2003.
14.
10.1016/j.mencom.2016.09.016_bib0070
Yang
Agrochemicals,
2013
15.
10.1016/j.mencom.2016.09.016_bib0075
Cauquis
C.R. Acad. Sci. Paris, Ser. C,
1968
16.
Gitkis A., Becker J.Y.
Electrochimica Acta,
2010
17.
Ananikov V.P., Khokhlova E.A., Egorov M.P., Sakharov A.M., Zlotin S.G., Kucherov A.V., Kustov L.M., Gening M.L., Nifantiev N.E.
Mendeleev Communications,
2015
18.
E. Terranova, A. Fadli and A. Lagrange, US Patent 6099593A, 2000.
19.
Mühmel G., Hanke R., Breitmaier E.
Synthesis,
1982