Synthesis and pharmacological activity of 4-aryl-1,4-dihydropyridines with fluorinated nitrogen-containing substituents in the benzene ring

Yagupol’skii, L. M.; Shavaran, S. S.; Klebanov, Boris; Rechitskii, A. N.; Maletina, I. I.

doi:10.1007/bf02218711

Cited by 2 publications

(3 citation statements)

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“…Efficient strategies towards N , N ‐bis(perfluoroalkyl)nitrogen compounds remain scarce, presumably, because of the lack of suitable starting materials [18,39–40] . Especially the N , N ‐bis(trifluoromethyl)amino group is of interest as its organic derivatives are known to exhibit high stability, for example against acids and bases, [1,41] and because its potential as substituent in pharmaceuticals was demonstrated, earlier [42–43] . N , N ‐Bis(trifluoromethyl)amino derivatives have been obtained from perfluoroazapropene CF 3 N=CF 2 as initial starting compound or through tedious reaction sequences [18,39,44] .…”

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confidence: 99%

“…[18,[39][40] Especially the N,N-bis (trifluoromethyl)amino group is of interest as its organic derivatives are known to exhibit high stability, for example against acids and bases, [1,41] and because its potential as substituent in pharmaceuticals was demonstrated, earlier. [42][43] N,N-Bis(trifluoromethyl)amino derivatives have been obtained from perfluoroazapropene CF 3 N=CF 2 as initial starting compound or through tedious reaction sequences. [18,39,44] Perfluoroazapropene is only accessible through laborious multistep syntheses, [45][46][47] it is a reactive gas that requires special equipment for handling, and its transformation into the synthetically useful bis(trifluoromethyl)amide ion N(CF 3 ) 2 is usually accompanied by dimerization giving CF 3 N=CFÀ N(CF 3 ) 2 (Figure 1).…”

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Stable and Storable N(CF₃)₂ Transfer Reagents

Schneider

Krauel

Deutsch

et al. 2021

Chemistry A European J

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Fluorinated groups are essential for drug design, agrochemicals, and materials science. The bis(trifluoromethyl) amino group is an example of a stable group that has a high potential. While the number of molecules containing perfluoroalkyl, perfluoroalkoxy, and other fluorinated groups is steadily increasing, examples with the N(CF 3 ) 2 group are rare. One reason is that transfer reagents are scarce and metalbased storable reagents are unknown. Herein, a set of Cu I and Ag I bis(trifluoromethyl)amido complexes stabilized by N-and P-donor ligands with unprecedented stability are presented. The complexes are stable solids that can even be manipulated in air for a short time. They are bis(trifluoromethyl) amination reagents as shown by nucleophilic substitution and Sandmeyer reactions. In addition to a series of benzylbis (trifluoromethyl)amines, 2-bis(trifluoromethyl)amino acetate was obtained, which, upon hydrolysis, gives the fluorinated amino acid N,N-bis(trifluoromethyl)glycine.Transition metal perfluoroalkyl complexes are highly valuable reagents for the synthesis of fluorinated biologically active molecules that are employed as pharmaceuticals or agrochemicals and in materials applications. [1][2][3][4][5][6] Especially, copper(I) complexes are important as they enable the introduction of a broad variety of perfluoroalkyl groups into organic molecules that range from the simplest congener, trifluoromethyl, to longer linear and branched perfluoroalkyl groups such as the heptafluoroisopropyl (hfip) group. [7][8][9][10] Although many of these complexes are used either in situ or immediately after generation, some complexes have been isolated and characterized, in detail. These complexes are often stabilized by co-ligands that typically are pyridines or phosphanes, for example [(bpy)CuC 2 F 5 ] (Figure 1) [11] and [(Ph 3 P) 2 Cu{CF(CF 3 ) 2 }] ([(Ph 3 P) 2 Cu(hfip)]). [12] Silver (I) complexes have been employed as perfluoroalkylation reagents as well, [13][14] although to a lesser extent than the related copper(I) derivatives. Because of their easy accessibility using silver(I) fluoride and the respective perfluoroalkene, for example, heptafluoropropene and tetrafluoroethylene, [15] they[a] L.

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confidence: 99%

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confidence: 99%

Stable and Storable N(CF₃)₂ Transfer Reagents

Schneider

Krauel

Deutsch

et al. 2021

Chemistry A European J

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“…N , N -bis(trifluoromethyl) amines represent another valuable motif due to their enhanced lipophilicity and stability in comparison to aliphatic and aromatic N -trifluoromethylamines. 20,21 Despite these interesting properties, access to N -(CF 3 ) 2 amines remains very scarce with most promising synthesis employing a combination of N , N -bis(trifluoromethyl)trifluoromethanesulphonamide and a metal-based reagent (Scheme 1C). 22…”

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confidence: 99%