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Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes
Author(s) -
Motornov Vladimir A.,
Tabolin Andrey A.,
Nelyubina Yulia V.,
Nenajdenko Valentine G.,
Ioffe Sema L.
Publication year - 2020
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.202000841
Subject(s) - chemistry , trifluoroacetic acid , annulation , substrate (aquarium) , atmospheric oxygen , organic chemistry , combinatorial chemistry , scope (computer science) , oxygen , catalysis , oceanography , computer science , programming language , geology
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.