Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes

Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2020, Volume: 2020, Number: 32, Pages: 5211-5219 Pages count : 9 DOI: 10.1002/ejoc.202000841

Authors

Motornov Vladimir A. ^1,2 , Tabolin Andrey A. ² , Nelyubina Yulia V. ³ , Nenajdenko Valentine G. ⁴ , Ioffe Sema L. ²

Affiliations

1	Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciencesm, Vavilov str. 28, 119991 Moscow, Russia
4	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, 119991 Moscow, Russia

A new approach for the synthesis of highly pharmaceutically relevant 4-fluoropyrazoles via oxidative annulation of α-fluoronitroalkenes with in situ prepared hydrazones was developed. The reaction is efficiently promoted by trifluoroacetic acid while atmospheric oxygen was used as an oxidant. Broad substrate scope was demonstrated, using both electron-rich and electron-deficient nitroalkenes as well as different hydrazones derived from aromatic aldehydes. The mechanistic details were also outlined.

Motornov V.A. , Tabolin A.A. , Nelyubina Y.V. , Nenajdenko V.G. , Ioffe S.L.
Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes
European Journal of Organic Chemistry. 2020. V.2020. N32. P.5211-5219. DOI: 10.1002/ejoc.202000841 WOS Scopus OpenAlex

≡ Web of science:	WOS:000555269000001
≡ Scopus:	2-s2.0-85088965173
≡ OpenAlex:	W3039928315