New synthetic approaches to 2-perfluoroalkyl-4H-pyran-4-ones

Tyvorskii, V. I.; Bobrov, D. N.; Kulinkovich, O. G.; Kimpe, Norbert De; Tehrani, Kourosch Abbaspour

doi:10.1016/s0040-4020(98)83018-4

Cited by 30 publications

(7 citation statements)

References 13 publications

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“…The starting 4-pyrones 3a, b and 5a were synthesized through cyclization of related 1,3,5-triketone derivatives under acidic conditions that is an important method for the synthesis of a variety of 4-pyrones particularly those having substituents at the 2 and 6 positions (Arimoto et al, 1990;Zawacki and Crim-mine, 1996;Tyvorskii et al, 1998;Li and Lacasse, 2002;Hobuss et al, 2005;Light and Hauser, 1960;Dorman, 1967;Harris et al, 1976). 2,6-Dimethyl-4H-pyran-4-one 5b is commercially available.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and calcium channel antagonist activity of novel 1,4-dihydropyridine derivatives possessing 4-pyrone moieties

et al. 2010

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New 1,4-dihydropyridine derivatives were synthesized by introducing 4-pyrone ring systems at the 4-position of the dihydropyridine nucleus. These compounds were obtained according to Hantzsch reaction. 4-Pyrone carbaldehydes: 4-(4-oxo-6-phenyl-4H-pyran-2-yl)-benzaldehyde 4a, 4-(6-methyl-4-oxo-4H-pyran-2-yl)benzaldehyde 4b, 4-oxo-6-phenyl-4H-pyran-2-carbaldehyde 7a, and 6-methyl-4-oxo-4H-pyran-2-carbaldehyde 7b were synthesized and used in these reactions. Then, the calcium channel blocking activity of some of these compounds were evaluated in which they showed weak effects.

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Section: Resultsmentioning

confidence: 99%

Synthesis and calcium channel antagonist activity of novel 1,4-dihydropyridine derivatives possessing 4-pyrone moieties

et al. 2010

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“…Similarly, 2-methyl-6-(trifluoromethyl)-4H-pyran-4-one and 2-methyl-6-(perfluoropropyl)-4H-pyran-4-one were synthesized from (E)-4-ethoxy-3-penten-2-one and R F CO 2 Et [8].…”

Section: Methodsmentioning

confidence: 99%

“…An approach to the synthesis of 2-CF 3 -4-pyrones, along with 2-C 3 F 7 -4-pyrones, has been proposed in 1998 [8], where epoxyketones 3 used as starting substrates. The method involves acylation of 3 with CF 3 CO 2 Et (C 3 F 7 CO 2 Et) in the presence of Bu t OK to 3-hydroxydihydropyrones 4, and treatment of 4 with SOCl 2 and pyridine giving rise to R F -pyrones 5 and some amounts of 3-chlorodihydropyrones 6.…”

Section: Methodsmentioning

confidence: 99%

“…Nevertheless, careful analysis of the literature data leads to the conclusion that 2-CF 3 -4-pyrones are convenient, available and versatile building-blocks and they could be used in regioselective syntheses of trifluoromethylated compounds much wider than it was shown earlier. Shortly thereafter, in 1998, some substituted derivatives of 2-CF 3 -4-pyrone were also described [8]. The first synthesis of such 2,6-disubstituted pyrones as 6-(trifluoromethyl)comanic (4-oxo-6-(trifluoromethyl)-4H-…”

Section: Introductionmentioning

confidence: 99%

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2-(Trifluoromethyl)-4H-pyran-4-ones: Convenient, available and versatile building-blocks for regioselective syntheses of trifluoromethylated organic compounds

Usachev

2015

Journal of Fluorine Chemistry

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“…Aldehyde 1b was synthesized from the corresponding ethoxycarbonyl derivative according to the reported procedure [27]. The ethoxycarbonyl derivative itself was prepared through cyclization of the related 1,3,5-triketone derivative under acidic conditions, which is an important method for the synthesis of a variety of 4-pyrone structures [28][29][30][31].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of fused pyrimidone derivatives of 4-pyrones from the acetates of Baylis–Hillman adducts

Shahrisa

Ghasemi

2010

Chem Heterocycl Comp

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A series of fused pyrimidone derivatives of 4-pyrones was synthesized by conversion of the acetates of Baylis−Hillman adducts obtained from 2-formyl-4-pyrones with 2-aminopyridine and 2-aminothiazole.The fused pyrimidine derivatives are of interest not only for their rich and varied synthetic chemistry but also for their important medicinal and physiological properties [1][2][3]. Therefore the synthesis of such derivatives has been an attractive area of a focus for synthetic organic and bioorganic chemists as well as numerous methods for the preparation of these heterocyclic compounds have been developed [4][5][6][7][8][9].The Baylis-Hillman reaction, a powerful tool for construction of a variety of cyclic and heterocyclic frameworks, has been used for the synthesis of various fused heterocyclic systems [10,11] such as fused pyrimidines. The reaction of 2-aminopyridine with acetates of Baylis-Hillman adducts leading to the formation of substituted fused pyrimidones has been reported [12]. Later the Baylis-Hillman products of acrylonitrile were used for the synthesis of annelated pyrimidine derivatives [13]. The allyl amine derivatives generated from acetates of Baylis-Hillman adducts have been also used as viable precursors for several fused pyrimidine derivatives [14][15][16][17].Heterocyclic substituted 4-pyrones have also been found in a variety of natural and synthetic biologically active compounds. Some of them are anticoagulants [18] or anti-HIV [19] agents. In continuation of our attempts in preparing various N-hetaryl-substituted 4-pyrones [20], we turned our attention to the synthesis of 4-pyrone derivatives containing a fused pyrimidone moiety. Since the Baylis-Hillman derivatives originating from substituted heterocyclic aldehydes have been known as excellent synthons for the synthesis of polycyclic ring systems, we first examined the Baylis-Hillman reactions of 2-formyl-4-pyrones that had not yet been reported. We describe in this report the results of these reactions and the reaction of acetates of these new adducts with 2-aminopyridine and 2-aminothiazole to afford fused pyrimidone derivatives in 4-pyrone structures.

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New synthetic approaches to 2-perfluoroalkyl-4H-pyran-4-ones

Cited by 30 publications

References 13 publications

Synthesis and calcium channel antagonist activity of novel 1,4-dihydropyridine derivatives possessing 4-pyrone moieties

Synthesis and calcium channel antagonist activity of novel 1,4-dihydropyridine derivatives possessing 4-pyrone moieties

2-(Trifluoromethyl)-4H-pyran-4-ones: Convenient, available and versatile building-blocks for regioselective syntheses of trifluoromethylated organic compounds

Synthesis of fused pyrimidone derivatives of 4-pyrones from the acetates of Baylis–Hillman adducts

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