• Title/Summary/Keyword: Pyrimidine

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Synthesis of Several New Isoxazole, Imidazo[1, 2-a]pyridine, Imidazo[1, 2-a]pyrimidine, Benzoxadiazine and Benzothiazine Derivatives from Hydroximoyl Halides

  • Abdelhamid, Abdou O.;Abdou, Sadek E.;Mahgoub, Sayed A.
    • Archives of Pharmacal Research
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    • v.15 no.4
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    • pp.317-321
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    • 1992
  • Furoyldroximoyl chloride 3d reacted with 2-aminopyridine, 2-aminopyrimidine. O-aminophenol, O-phenylenediamine and aminothiophenol to afford imidazo [1, 2-a]pyridine 6. imidazo[1, 2-a]pyrimidine 8, benzoxadiazine 10, nitrosobenzopyrizine 13a and nitrosobenzothiazine 13b, respectively. Isoxazoline 18 and pyrrolidino[3, 4-d]isoxazolin-4, 6-dione derivatives 19a and 19b obtained by the reaction of 3 with acrylonitrile and N-arylmaleimide. Hydroximoyl chloride 3 reacted with thiophenol and sodium benzene-sulfinate to yield furylglyoxaloxime 16a and 16b, respectively. Hydroximoyl chloride 3 reacted also with some active methylene compound to give isoxazole derivatives 20-23, respectively.

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Synthesis of N,N-Diaryl-(pyridin-3-yl)pyrimidin-2-amine Derivatives and Their Photochemical Properties

  • El-Deeb, Ibrahim Mustafa;Lee, So-Ha
    • Journal of the Korean Applied Science and Technology
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    • v.25 no.3
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    • pp.291-298
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    • 2008
  • Although the pyrimidine derivatives were obtained in low yields ranging from 8% to 20%, we reported the successful preparation of N,N-diaryl-pyrimidin-2-amine derivatives starting from the corresponding 2-aminopyrimidines (1a-1c), by direct palladium-catalyzed arylation using different arylbromides. The reasons of low yields are thought to be the electronic and steric effects by the neighboring aromatic systems. The absorption spectra and photoluminescent spectra of compounds (3a 3g and 4a-4c) were measured using dichloromethane on the concentration of 25 mM by UV vis spectroscopy and luminescent spectroscopy. Pyrimidine derivatives 4a, 4b, and 4c showed moderate emission maxima at 474 nm, 481 nm, and 367 nm, respectively, while other compounds showed very weak photoluminescence or no photoluminescence at all.

Synthesis of D-1,3-Dioxolane and L-1,3-Oxathiolane 5-Phenylselenyl Pyrimidine Nucleosides as Potential Antiviral Agents (D-1,3-디옥솔란 및 L-1,3-옥사티올란 5-페닐세레닐 피리미딘 뉴크레오사이드의 합성)

  • Yoo, Jung-Man;Moon, Hyun-Ju;Chung, Byung-Ho;Choi, Bo-Gil;Hong, Joong-Hee;Chun, Moon-Woo
    • YAKHAK HOEJI
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    • v.40 no.1
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    • pp.46-51
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    • 1996
  • Eight new D-1.3-dioxolanyl and L-1,3-oxathiolanyl nucleosides containing 5-phenyl- selenyl pyrimidine bases which are expected to have antiviral activity were synthesized. Condensation of D-1,3-dioxolane acetate and L-1,3-oxathiolane acetate with 5-phenylselenyl pyrimidines gave anomeric mixtures of their nucleosides which were separated by silicagel column chromatography.

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Solid-phase Synthesis and Preliminary Evaluation of 1,6,8-Trisubstituted Tetrahydro-2H-pyrazino[1,2-a]pyrimidine-4,7-diones as a NF-kB Inhibitor

  • Kim, Jin-Woong;Cho, Jung-Hyuck;Han, Tae-hee;Lee, Jong-Baek;Oh, Chang-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.27 no.4
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    • pp.484-488
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    • 2006
  • The solid-phase synthesis of new series of 1,6,8-trisubstituted tetrahydro-2H-pyrazino[1,2-a]pyrimidine-4,7-diones as bicyclic $\beta$-turn mimetics is described. Their NF-kB inhibition activities were tested and the effect of substituents on bicyclic ring was investigated. Among the prepared compounds, the fluorobenzyl and methoxybenzyl group substituted compounds 26 and 27 at C-1 and C-8 position showed more inhibitory activities than the others. Tested at a concentration of 10 uM, these two compounds showed a 60% inhibition against the target NF kB 549.

A Facile One-pot Synthesis of Fused 2-Thiouracils: Dipyrimidinopyridine, Pyrazolopyrimidine and Pyridazinopyrimidines

  • Youssif, Shaker;EI-Bahaie, Said;Nabih, Esam
    • Bulletin of the Korean Chemical Society
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    • v.24 no.10
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    • pp.1429-1432
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    • 2003
  • A novel fused thiouracil containing a heterocyclic ring system, dipyrimidinopyridine (3), has been prepared through the cyclization of compound 2. Compound 2 was formed by the formylation of 6-amino-2-thiouracil 1, pyrazolopyrimidines 8-10 via the heating of 6-arylhydrazono-2-thiouracils 5-7, compound 11, using Vilsmeier reagent with compound 4, pyrazolylpyrimidine 12, indolodiazinopyrimidine 14 and pyridazinopyrimidine 15. Pyridazino-pyrimidine 15 was formed by the condensation of compound 4 with acetylacetone, isatin and benzyl, respectively.

Synthesis of Some New Condensed Pyrimidine Derivatives

  • Mohamed, Enaiat K.;Shehab, Wesam S.
    • Journal of the Korean Chemical Society
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    • v.55 no.6
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    • pp.988-993
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    • 2011
  • Cyclodehydration of 6-amino-5-cyano pyrimidine derivative (2) afforded pyrimidoisoindole derivatives (3). Compound (3) reacted with carbethoxymethylene derivative to give pyridopyrimidine derivatives (5a,b). Compound (3) was also reacted with formamide to give the corresponding pyrimidopyrimdine derivatives (6) that condensed with benzaldehyde to give Schiff's base (7). Refluxing of compound (3) with triethyl orthoformate afforded compound (8) that cyclized with ammonium hydroxide giving the same compound (6). Compound (8) cyclized with hydrazine hydrate giving compound (9) which also cyclized with triethyl orthoformate affording compound (10). Diazotization of compound (3) led to the formation of triazinopyrimidine derivative (11). Cyclization of compound (11) upon treatment with hydrazine hydrate afforded compound (12). Compound (15) was prepared from reaction of compound (3) and ethylenediamine in presence of carbon disulfide. The behaviour of compound (15) toward benzoyl chloride, triethyl orthoformate, nitrous acid and/or carbon disulfide was also described. All proposed structures were supported by elemental analyses, spectroscopic data and some of the new products showed antimicrobial activity.

Loss of HCN from the Pyrimidine Molecular Ion: A Computational Study

  • Yim, Min Kyoung;Jung, Sun Hwa;Kim, Myung Soo;Choe, Joong Chul
    • Bulletin of the Korean Chemical Society
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    • v.33 no.12
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    • pp.4098-4102
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    • 2012
  • The potential energy surface (PES) for the loss of HCN from the pyrimidine molecular ion has been explored using quantum chemical calculations. Possible reaction pathways to form five $C_3H_3N^{+{\bullet}}$ isomers have been obtained with Gaussian 4 model calculations. The rate constant for the HCN loss and the product branching ratio have been calculated using the Rice-Ramsperger-Kassel-Marcus theory on the basis of the obtained PES. The resultant rate constant agrees with the previous experimental result. By a kinetic analysis, it is proposed that the formation of $CH=CHC{\equiv}NH^{+{\bullet}}$ is favored near the dissociation threshold, while the formation of $CH=CHN{\equiv}CH^{+{\bullet}}$ is favored at high energies.

Synthesis of New 5-Benzyl-4-cyanomethyl-2-methylpyrimidine Derivatives (새로운 5-Benzyl-4-cyanomethyl-2-methylpyrimidine 유도체들의 합성)

  • Kim, Jung Hwan;Han, Mun Su
    • Journal of the Korean Chemical Society
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    • v.40 no.4
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    • pp.249-253
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    • 1996
  • The synthesis of new 5-benzyl-4-cyanomethyl-2-methylpyrimidine derivatives (5) containing chloro, methoxy, ethoxy, phenoxy and anilino groups at 6-position on the pyrimidine ring were prepared from 5-benzyl-4-chloro-2-methylpyrimidine derivatives (3) and tert-butylcyanoacetate. The derivatives of 5-benzyl-4-chloro-2-methylpyrimidine (3) containing chloro, methoxy, ethoxy, isopropoxy, phenoxy and anilino groups at 6-position on the pyrimidine ring were prepared from 5-benzyl-4,6-dichloro-2-methylpyrimidine (2).

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