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 CF3 Groups. Issue 15 (23rd April 2019)

• Record Type: Journal Article
• Authors: Yagupolskii, Yurii L.; Pavlenko, Natalia V.; Gerus, Igor I.; Peng, Sheng; Nappa, Mario
• Is Part Of: ChemistrySelect. Volume 4:Issue 15(2019)
• Page Start: 4604
• Page End: 4610
• Publication Date: 2019-04-23
• Subjects: Cycloaddition -- Dipole -- Hexafluorobutyne -- Isoxazole -- Pyrazole -- Pyrazoline; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201900387
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: This project involves the syntheses of novel pyrazoles, pyrazolines and isoxazoles with two CF3 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 CF3 groups are practically unknown up to date. Abstract : An efficient route to the syntheses of novel pyrazoles, pyrazolines and isoxazoles with two CF3 groups via 1, 3‐dipolar cycloaddition reaction of 1, 1, 1, 4, 4, 4‐hexafluorobut‐2‐ynewith diazocompounds, azomethine imines and nitrile oxides was elaborated. Catalyst‐free mild conditions, a high functional group tolerance and yields of target heterocycles from moderate to excellent were demonstrated.