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Synthesis and Regioselective N‐2 Functionalization of 4‐Fluoro‐5‐aryl‐1,2,3‐N H ‐triazoles
Author(s) -
Motornov Vladimir A.,
Tabolin Andrey A.,
Novikov Roman A.,
Nelyubina Yulia V.,
Ioffe Sema L.,
Smolyar Ivan V.,
Nenajdenko Valentine G.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701338
Subject(s) - regioselectivity , chemistry , surface modification , aryl , sulfamic acid , combinatorial chemistry , domino , organic chemistry , catalysis , alkyl
A new efficient synthetic route to 4‐fluoro‐5‐aryl‐1,2,3‐N H ‐triazoles was elaborated. The reactions of NaN 3 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.