Tautomerism of 5-fluoro-4-hydroxy-2-methoxypyrimidine. Conditions for stabilization of the zwitterionic tautomer

Kheifets, G. M.; Gindin, V. A.; Studentsov, E. P.

doi:10.1134/s1070428006040166

Cited by 2 publications

(2 citation statements)

References 14 publications

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“…For cyclic systems such as 4-hydroxypyrimide, in which the iminol form represents an aromatic system, one would expect greater iminol content. In fact, this does seem to be true in the gas phase, where the equilibrium has been reported to be near unity, although the oxo form is again thought to predominate in either solution or the crystalline state . For compound 10 , the combination of a cyclic system capable of an aromatic form and two different amide groups both able to undergo tautomerism could further favor the iminol form.…”

Section: Resultsmentioning

confidence: 99%

“…In fact, this does seem to be true in the gas phase, where the equilibrium has been reported to be near unity, although the oxo form is again thought to predominate in either solution or the crystalline state. 34 For compound 10, the combination of a cyclic system capable of an aromatic form and two different amide groups both able to undergo tautomerism could further favor the iminol form. However, this does not seem to be the case, and the determined solid-state structure of 10 appears to consist exclusively of the dione tautomer.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials

Schwiderski

Rasmussen

2013

J. Org. Chem.

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Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5,7-bis(2-thienyl)thieno[3,4-b]pyrazines. From these reactive intermediates, a variety of new 2,3-difunctionalized 5,7-bis(2-thienyl)thieno[3,4-b]pyrazines have been produced as precursors to conjugated materials. Structural, electronic, and optical characterization of these new analogues illustrate the extent to which the electronic nature of the functional groups can be used to tune the electronic properties of these thieno[3,4-b]pyrazine-based terthienyl units.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials

Schwiderski

Rasmussen

2013

J. Org. Chem.

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Novel 5-Fluorouracil Derivatives: Synthesis and Cytotoxic Activity of 2-Butoxy-4-Substituted 5-Fluoropyrimidines

Sun¹,

Zhang²,

Li³

et al. 2013

Bulletin of the Korean Chemical Society

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Twenty two new 5-fluorouracil (5-FU) derivatives, 2-butoxy-4-substituted 5-fluoropyrimidines, were synthesized and characterized by IR, 1 H NMR, MS, HRMS. All compounds were preliminarily evaluated by MTT assay on human liver BEL-7402 cancer cell line in vitro. Ten compounds were selected to test their cytotoxic activity against A549, HL-60 and MCF-7 cancer cell lines in vitro. These compounds were more sensitive to BEL-7402 than other cell lines, particularly, cytotoxic activity of compounds 6b, 6d-f, 6p, 6s-u were in sub-micromolar scale. The highest cytotoxic potency against A549, HL-60 and MCF-7 was shown by 2-butoxy-4-chloro-5-fluoropyrimidine (5) with IC 50 values of 0.10, 1.66 and 0.59 µM, respectively. Compounds 6d and 6e were effective against MCF-7 with IC 50 9.73 µM and HL-60 with IC 50 8.83 µM, respectively.

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Tautomerism of 5-fluoro-4-hydroxy-2-methoxypyrimidine. Conditions for stabilization of the zwitterionic tautomer

Cited by 2 publications

References 14 publications

Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials

Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials

Novel 5-Fluorouracil Derivatives: Synthesis and Cytotoxic Activity of 2-Butoxy-4-Substituted 5-Fluoropyrimidines

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