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

Тимошенко, Вадим М.; Nikolin, Yarema V.; Chernega, Alexander N.; Shermolovich, Yu. G.

doi:10.1002/1099-0690(200205)2002:10<1619::aid-ejoc1619>3.0.co;2-8

Cited by 13 publications

(2 citation statements)

References 24 publications

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“…The two CO bond lengths found for 11 are almost equal (O(2)C(2) 1.2285(13) and O(4)C(4) 1.2387(15) Å, respectively) (Figure 7) and are within the range of the CO bonds found for similar compounds, such as 1,3,6‐trisubstituted uracils (1,3‐Me‐6‐R‐2‐U) (C1O(1) 1.233(3) (R = Me), 1.224(2) (R = Et), 1.212(3), 1.221(3), 1.220(3) (R = n Pr), and 1.220(5) 1.226(5) (R = n Bu),22a Triethylammonium 2,4‐dioxo‐6‐(1,1,2,2,3,3‐hexafluoropropyl)‐5‐benzylsulfonyl‐3 H ‐2,4‐dihydropyrimidine22b (C(2)O(1) 1.235(3) and C(4)O(2) 1.237(2) Å).…”

Section: Resultssupporting

confidence: 59%

Synthesis and Structures of Se Analogues of the Antithyroid Drug 6‐n‐Propyl‐2‐thiouracil and Its Alkyl Derivatives: Formation of Dimeric Se–Se Compounds and Deselenation Reactions of Charge‐Transfer Adducts of Diiodine

Antoniadis

Hadjikakou

Hadjiliadis

et al. 2006

Chemistry A European J

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Four selenium analogues of the antithyroid drug 6-n-propyl-2-thiouracil (PTU), of formulae RSeU, (R = methyl (Me) (1), ethyl (Et) (2), n-propyl (nPr) (3), and isopropyl (iPr) 4), have been synthesized. Reaction of 1-4 with diiodine in a 1:1 molar ratio in dichloromethane results in the formation of [(RSeU)I(2)] (R = methyl (5), ethyl (6), n-propyl (7) and isopropyl (8)). All compounds have been characterized by elemental analysis, FT-Raman, FT-IR, UV/Vis, (1)H-, (13)C-, (77)Se-1D and -2D NMR spectroscopy, and ESI-MS spectrometric techniques. Recrystallization of 4 from dichloromethane afforded (4CH(2)Cl(2)). Crystals of [(nPrSeU)I(2)] (7), a charge-transfer complex, were obtained from chloroform solutions, while crystallization of 6 and 7 from acetone afforded the diselenides [N-(6-Et-4-pyrimidone)(6-EtSeU)(2)] (92 H(2)O) and [N-(6-nPr-4-pyrimidone)(6-nPrSeU)(2)] (10) as oxidation products. Recrystallization of 7 from methanol/acetonitrile solutions led to deselenation with the formation of 6-n-propyl-2-uracil (nPrU) (11). [(nPrSeU)I(2)] (7) was found to be a charge-transfer complex with a Se--I bond. These results are discussed in relation to the mechanism of action of antithyroid drugs.

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Section: Resultssupporting

confidence: 59%

Synthesis and Structures of Se Analogues of the Antithyroid Drug 6‐n‐Propyl‐2‐thiouracil and Its Alkyl Derivatives: Formation of Dimeric Se–Se Compounds and Deselenation Reactions of Charge‐Transfer Adducts of Diiodine

Antoniadis

Hadjikakou

Hadjiliadis

et al. 2006

Chemistry A European J

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“…The C-Se bond distances in (1)-(4) and in (4ÁCH 2 Cl 2 ) vary from 1.824 (2) to 1.848 (6) Å ( Table 2). The two C O bond distances found in (11) are almost equal [1.2286 (16), 1.2387 (16) Å ; Table 4] and are within the range of the C O bonds found for other similar compounds such as 1,3-di-methyl-6-R-trisubstituted uracils [R = Me, 1.233 (3) Å ; R = Et, 1.224 (2) Å ; R = n Pr, 1.212 (3), 1.221 (3), 1.220 (3) Å ; R = n Bu, 1.220 (5), 1.226 (5) Å ; Suwinska, 1995] and triethylammonium 2,4-dioxo-6-(1,1,2,2,3,3-hexafluoropropyl)-5-benzylsulfonyl-3H-2,4-dihydropyrimidine [1.235 (3), 1.237 (2) Å ] (Timoshenko et al, 2002).…”

Section: Resultssupporting

confidence: 67%

Structural characterization of selenium and selenium-diiodine analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives

Antoniadis

Blake

Hadjikakou

et al. 2006

Acta Crystallogr B Struct Sci

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The structures of four selenium analogues of the antithyroid drug 6-n-propyl-2-thiouracil [systematic name: 2,3-dihydro-6-n-propyl-2-thioxopyrimidin-4(1H)-one], namely 6-methyl-2-selenouracil, C(5)H(6)N(2)OSe (1), 6-ethyl-2-selenouracil, C(6)H(8)N(2)OSe (2), 6-n-propyl-2-selenouracil, C(7)H(10)N(2)OSe (3), and 6-isopropyl-2-selenouracil, C(7)H(10)N(2)OSe (4), are described, along with that of the dichloromethane monosolvate of 6-isopropyl-2-selenouracil, C(7)H(10)N(2)OSe.CH(2)Cl(2) (4.CH(2)Cl(2)). The extended structure of (1) is a two-dimensional sheet of topology 6(3) with a brick-wall architecture. The extended structures of (2) and (4) are analogous, being based on a chain of eight-membered R(8)(6)(32) hydrogen-bonded rings. In (3) and (4.CH(2)Cl(2)), R(2)(2)(8) hydrogen bonding links molecules into chains. 6-n-Propyl-2-selenouracil.I(2), C(7)H(10)N(2)OSe.I(2) (7), is a charge-transfer complex with a ;spoke' structure, the extended structure of which is based on a linear chain formed principally by intermolecular N-H...O hydrogen bonds. Re-crystallization of 6-ethyl-2-selenouracil or (7) from acetone gave crystals of the diselenides [N-(6'-ethyl-4'-pyrimidone)(6-ethyl-2-selenouracil)(2)(Se-Se)].2H(2)O (9.2H(2)O) or [N-(6'-n-propyl-4'-pyrimidone)(6-n-propyl-2-selenouracil)(2)(Se-Se)] (10), respectively: these have similar extended chain structures formed via N-H...O and C-H...O hydrogen bonds, stacked to give two-dimensional sheets. Re-crystallization of (7) from methanol/acetonitrile led via deselenation to the formation of crystals of 6-n-propyl-2-uracil (11), in which six symmetry-related molecules combine to form a six-membered R(6)(6)(24) hydrogen-bonded ring, with each pair of molecules linked by an R(2)(2)(8) motif.

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Synthesis of Fluorine‐Containing Heterocycles from α,α‐Dihydropolyfluoroalkylsulfides and Fluorinated Thiocarboxylic Acids Derivatives

Timoshemko

Shermolovich

2012

Efficient Preparations of Fluorine Compounds

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

Cited by 13 publications

References 24 publications

Synthesis and Structures of Se Analogues of the Antithyroid Drug 6‐n‐Propyl‐2‐thiouracil and Its Alkyl Derivatives: Formation of Dimeric Se–Se Compounds and Deselenation Reactions of Charge‐Transfer Adducts of Diiodine

Synthesis and Structures of Se Analogues of the Antithyroid Drug 6‐n‐Propyl‐2‐thiouracil and Its Alkyl Derivatives: Formation of Dimeric Se–Se Compounds and Deselenation Reactions of Charge‐Transfer Adducts of Diiodine

Structural characterization of selenium and selenium-diiodine analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives

Synthesis of Fluorine‐Containing Heterocycles from α,α‐Dihydropolyfluoroalkylsulfides and Fluorinated Thiocarboxylic Acids Derivatives

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