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Synthesis and Regioselective N‐2 Functionalization of 4‐Fluoro‐5‐aryl‐1,2,3‐NH‐triazoles Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2017, Volume: 2017, Number: 46, Pages: 6851-6860 Pages count : 10 DOI: 10.1002/ejoc.201701338
Authors Motornov Vladimir A. 1,2 , Tabolin Andrey A. 2 , Novikov Roman A. 2,3 , Nelyubina Yulia V. 4 , Ioffe Sema L. 2 , Smolyar Ivan V. 5 , Nenajdenko Valentine G. 5
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 V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, 119991 Moscow, Russia
4 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991 Moscow, Russia
5 Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, 119991 Moscow, Russia

Abstract: A new efficient synthetic route to 4-fluoro-5-aryl-1,2,3-NH-triazoles was elaborated. The reactions of NaN3 with aryl-substituted α-fluoronitroalkenes resulted in the domino construction of the target fluorinated triazoles. Sulfamic acid is an effective promoter for this heterocyclization. The subsequent functionalization reactions of the obtained triazoles proceed highly regioselectively at the N-2 position. The observed regioselectivity was supported by DFT calculations.
Cite: Motornov V.A. , Tabolin A.A. , Novikov R.A. , Nelyubina Y.V. , Ioffe S.L. , Smolyar I.V. , Nenajdenko V.G.
Synthesis and Regioselective N‐2 Functionalization of 4‐Fluoro‐5‐aryl‐1,2,3‐NH‐triazoles
European Journal of Organic Chemistry. 2017. V.2017. N46. P.6851-6860. DOI: 10.1002/ejoc.201701338 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:000418147300005
≡ Scopus: 2-s2.0-85038079736
≡ OpenAlex: W2761398453
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