A concise approach to CF3-containing furan-3-ones, (bis)pyrazoles from novel fluorinated building blocks based on 2,3-butanedione

Bazhin, D. N.; Chizhov, D. L.; Röschenthaler, Gerd‐Volker; Kudyakova, Yulia S.; Burgart, Yanina V.; Слепухин, П. А.; Салоутин, В. И.; Charushin, Valery N.

doi:10.1016/j.tetlet.2014.08.046

Cited by 36 publications

(26 citation statements)

References 58 publications

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“…Representative examples are shown in Figure 4. [25,26] Even though diatomic fluorine was first used to prepare alkyl fluorides more than a century ago, its highly reactive nature limited its utility as a fluorinating agent. [27] About seventy years ago, development of reagents began which could selectively deliver fluorine and fluorine-containing moieties under less stringent conditions.…”

Section: Introductionmentioning

confidence: 99%

Selective Incorporation of Fluorine in Pyrazoles

2015

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Pyrazoles are highly essential heterocyclic structures prevalent in biologically active products used widely throughout various disciplines of chemical industry‐including medicine and agriculture. The efficacy of these pyrazole species is enhanced through the introduction of fluorine and corresponding functionalities; therefore, synthetic methods for the fluorination of these structures is highly appealing which follows the overall trend of increasing interest in fluorination chemistry. Toward assimilating the known techniques for fluorine incorporation to the pyrazole heterocyclic structure we have reviewed both the new and traditional synthetic approaches to the assembly of functionalized pyrazole derivatives. Specifically, efficient synthetic methods and regioselective incorporation of fluorine and fluorine containing functional groups into different pyrazole ring systems are examined.

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Section: Introductionmentioning

confidence: 99%

Selective Incorporation of Fluorine in Pyrazoles

2015

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“…[4‐(Aminosulfonyl)phenyl]hydrazine monohydrochloride ( 15e ), 4‐methylbenzenesulfonohydrazide ( 17c ) were prepared according to the reported procedures 20,21. 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2 H )‐one ( 11 ) was obtained according to the method earlier reported 9 . 1 H, 19 F and 13 C NMR spectra were recorded on Bruker DRX‐400 and AVANCE‐500 spectrometers in [D 6 ]DMSO, CDCl 3 or [D 6 ]acetone using Me 4 Si and C 6 F 6 as internal standards.…”

Section: Methodsmentioning

confidence: 99%

“…In our attempts to expand the chemistry of trifluoromethyl‐containing 1,3,4‐triketones we have realized the direct trifluoroacetylation of 2,3‐butanedione acetal derivatives followed by their successful conversion into CF 3 ‐pyrazoles 7 – 9 and 5,5′‐bis(trifluoromethyl)‐3,3′‐bipyrazole ( 10 ) (Figure 2). 9 It has been found that acid‐catalyzed transformation of lithium (2 Z )‐1,1,1‐trifluoro‐5,5‐dimethoxy‐4‐oxohex‐2‐en‐2‐olate ( 6 ) affords 2‐methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2 H )‐one ( 11 ) (Figure 3). 9…”

Section: Introductionmentioning

confidence: 99%

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A Convenient Approach to CF₃‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one

et al. 2015

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New synthetic routes to trifluoromethylated N‐heterocycles based on condensations of 2‐methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one with bifunctional N‐nucleophiles are described. For the first time, trifluoromethyl‐containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one‐pot strategy based on reactions of 5‐(trifluoromethyl)furan‐3(2H)‐one with two equivalents of the corresponding hydrazines or hydroxylamine in the presence of an acid. The interaction of furan‐3(2H)‐one with ureas proceeded under mild conditions to furnish 1H‐furo[2,3‐d]imidazol‐2(3H)‐one derivatives in good yield. Further, a trifluoromethyl‐containing quinoxaline derivative was obtained by condensation of furan‐3(2H)‐one with ortho‐phenylenediamine.

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“…Recently, we have shown the functionalized lithium CF 3 ‐β‐diketonate[11a] to be an efficient ligand in the synthesis of lanthanide‐based complexes [(LnL 3 )(LiL)(solv)] with formally tetrakis(β‐diketonate) structure. [11b] The additional coordination of methoxy substituent with metal ions resulted in the formation of unusual Ln–Li dinuclear framework. The use of alkali metal β‐diketonates is a versatile method for the preparation of heterometallic polynuclear assemblies with stoichiometric composition.…”

Section: Introductionmentioning

confidence: 99%

The Impact of the Alkali Metal Ion on the Crystal Structure and (Mechano)luminescence of Terbium(III) Tetrakis(β‐diketonates)

et al. 2019

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The novel terbium(III) tetrakis(β‐diketonates) M[TbL4] with different alkali metal counterions (Na, K, Cs) based on functionalized trifluoromethylated β‐diketonate are reported. An efficient approach to alkali metal β‐diketonates ML (M = Na, K, Cs) is proposed, which does not require the alkaline media promoting the destruction of 1,3‐dicarbonyl compounds. The transformation of lithium β‐diketonate LiL into the corresponding alkali metal β‐diketonate ML has been achieved under mild conditions using alkali metal fluorides. Organic ligand generates the multiplicity of coordination modes through a diketonate fragment, methoxy group and trifluoromethyl substituent. The alkali metal ion changes the geometry of coordination environment of the terbium(III) ion and affects the crystal packing of complexes. The additional coordination centers in the ligand coupled with a small atomic radius of sodium ion resulted in a construction of a rare example of discrete lanthanide tetrakis(β‐diketonate) Na[TbL4]. Moreover, this complex exhibited bright luminescence and mechanoluminescence in contrast to polymeric TbIII tetrakis(β‐diketonates) with K and Cs.

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A concise approach to CF3-containing furan-3-ones, (bis)pyrazoles from novel fluorinated building blocks based on 2,3-butanedione

Cited by 36 publications

References 58 publications

Selective Incorporation of Fluorine in Pyrazoles

Selective Incorporation of Fluorine in Pyrazoles

A Convenient Approach to CF₃‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one

The Impact of the Alkali Metal Ion on the Crystal Structure and (Mechano)luminescence of Terbium(III) Tetrakis(β‐diketonates)

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A concise approach to CF3-containing furan-3-ones, (bis)pyrazoles from novel fluorinated building blocks based on 2,3-butanedione

Cited by 36 publications

References 58 publications

Selective Incorporation of Fluorine in Pyrazoles

Selective Incorporation of Fluorine in Pyrazoles

A Convenient Approach to CF3‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one

The Impact of the Alkali Metal Ion on the Crystal Structure and (Mechano)luminescence of Terbium(III) Tetrakis(β‐diketonates)

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A Convenient Approach to CF₃‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one