Synthesis of difluorodithiopyruvic acid derivatives

Shermolovich, Yurii G.; Тимошенко, Вадим М.; Listvan, Vitalii V.; Markovskii, L. N.

doi:10.1070/mc1998v008n06abeh000971

Cited by 5 publications

(4 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction probably proceeds by nucleophilic substitution of the vinylic fluorine atom in I by the isocyanate group, with intermediate formation of vinyl isocyanate II. Only triethylammonium cyanate III, formed by reaction between sodium cyanate and triethylamine hydrofluoride, can be the source of the isocyanate ion, since isolated vinyl fluorides I in the 1.714 (12) [d] C(6)N(1)C(2) 117.8 (2) 119.5(2) 114.6(2) 117.9(11) N(1)C(2)N(3) 118.4 (2) 119.0(2) 129.6(2) 125.2(12) C(2)N(3)C(4) 125.6 (2) 123.5 (2) 116.53 (2) 116.4(10) N(3)C(4)C(5) 114.5 (2) 114.8 (2) 119.6(2) 124.0(10) C(4)C(5)C(6) 116.5 (2) 118.2(2) 116.6(2) 114.2(10) C(5)C(6)N(1) 125.6 (2) 123.9(2) 122.9(2) 121.7 (11) [a] Average values for two independent molecules. [b] C (2)ϪCl (1) distance.…”

Section: Resultsmentioning

confidence: 99%

“…[11] In previous works we have reported on the preparation and properties of polyfluoro-1,1-dihydroalkyl sulfones 1 Ϫ new reagents for the synthesis of fluorine-containing compounds. We have described the application of sulfones 1 for the preparation of enamines, imines, and ketones, [12] and of hydrazones, osazones and pyrazoles. [13] In the presence of tertiary amines, sulfones 1 react with sodium azide to give pounds 7 with polyfluoroalkyl substituents of different lengths showed differing reactivities in reactions with ammonia and methanol.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Treatment of Polyfluoro-1,1-dihydroalkyl Sulfones with Sodium Cyanate and Triethylamine: A New Method for the Synthesis of 6-(Polyfluoroalkyl)uracils

et al. 2002

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Treatment of Polyfluoro-1,1-dihydroalkyl Sulfones with Sodium Cyanate and Triethylamine: A New Method for the Synthesis of 6-(Polyfluoroalkyl)uracils

et al. 2002

View full text Add to dashboard Cite

“…1. The central pyrazole ring C (1) C (2) C (3) N (2) N (1) is virtually planar; the deviation from the mean square plane does not exceed 0.005 Å. Steric hindrance forces benzene rings C (5) -C (10) and C (11) -C (16) to be twisted almost orthogonally to the central benzene ring; the corresponding dihedral angles are 80.68° and 74.48°.…”

mentioning

confidence: 91%

“…Enaminones 2a,b were obtained by the Vilsmeier-Haack-Arnold reaction [9] from 1-arylsulfonyl-1,1-dihydropolyfluoro-2-alkanone hydrates 3a,b [10]. This reaction proceeds at room temperature.…”

mentioning

confidence: 99%

Synthesis of 5-polyfluoroalkyl-4-(p-tolyl-sulfonyl)pyrazoles and 4-polyfluoroalkyl-5-(p-tolylsulfonyl)pyrimidines from 1-dimethylamino-2-(p-tolylsulfonyl)-polyfluoro-1-alken-3-ones

Kanishchev

Bandera

Тимошенко

et al. 2007

Chem Heterocycl Compd

View full text Add to dashboard Cite

Keywords: 1-arylsulfonyl-1,1-dihydropolyfluoro-2-alkanone, enaminone, pyrazole, pyrimidine, Vilsmeier-Haack-Arnold reaction, X-ray diffraction structural analysis.Fluoropyrazoles and fluoropyrimidines display a variety of strong biological activities [1][2][3][4][5], which has led to work to develop new methods for the synthesis of such heterocyclic compounds.The synthetic approaches for the heterocyclic pyrazole system have been studied extensively. The most common approach involves a reaction, in which the three-carbon fragment of a β-dicarbonyl compound or its synthetic equivalent is condensed with the diatomic N-N fragment of hydrazine or its derivative. A problem with this approach is the regioselectivity of the reaction using asymmetric starting compounds since a mixture of N-substituted pyrazoles is formed in most cases [6]. The similar reaction of β-dicarbonyl compounds with a binucleophile possessing an N-C-N fragment leads to the formation of pyrimidines and is also frequently used for the design of these heterocycles [7].In the present work, we studied the feasibility of using 1-dimethylamino-2-(p-tolylsulfonyl)-polyfluoro-1-alken-3-ones 2a,b, which are the synthetic equivalents of a new type of β-dicarbonyl compounds, namely, 1-arylsulfonyl-2-oxopolyfluoroalkanals 1a,b for the regioselective synthesis of fluoropyrazoles and fluoropyrimidines. Monoenamines of various 1,3-dicarbonyl compounds (amide vinylogs) have found common use in the synthesis of many heterocyclic systems [8].

show abstract