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1,1,1,4,4,4‐Hexafluorobut‐2‐yne (HFB) as a Versatile Dipolarophile for [3+2] Cycloaddition with 1,3‐Dipoles toward Azoles with Adjacent CF 3 Groups
Author(s) -
Yagupolskii Yurii L.,
Pavlenko Natalia V.,
Gerus Igor I.,
Peng Sheng,
Nappa Mario
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900387
Subject(s) - cycloaddition , nitrile , catalysis , functional group , chemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , polymer
This project involves the syntheses of novel pyrazoles, pyrazolines and isoxazoles with two CF 3 groups via 1,3‐dipolar cycloaddition reaction of 1,1,1,4,4,4‐hexafluorobut‐2‐yne ( HFB ) with diazocompounds, azomethine imines and nitrile oxides, respectively. Conditions for these azoles preparation differ in catalyst‐free mild manners and are applicable to a wide range of substrates, while demonstraiting a high functional group tolerance with yields of target heterocycles from moderate to excellent. Indeed, pyrazolines bearing two adjacent CF 3 groups are practically unknown up to date.