15018-56-1Relevant articles and documents
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Nishiwaki,Goto
, p. 26 (1960)
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Johnson
, (1944)
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Sasaki,Ando
, p. 2215 (1968)
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Fe(III) and cobalt(II) coordination compounds of 5-bromo-6-methyl-2- morpholinepyrimidinium-4-amine pyridine-2,6-dicarboxylate
Eshtiagh-Hosseini, Hossein,Yousefi, Zakieh,Shafiee, Maryam,Mirzaei, Masoud
, p. 3187 - 3197 (2010)
New coordination compounds, (bmmpaH)[Fe(pydc)2] (EtOH) 0.8(H2O)0.2 (1), (8QH)[Fe(pydc)2] H2O (2), (2ampyH)2[Mn(pydc)2] H2O (3), (2ampyH)[Cr(pydc)2](2ampy)0.5 H2O (4), [Co(H2O)5-μ (pydc)Co(pydc)] 2H2O (5), [Ni(pydcH)2] H2O (6), and [Cu(pydcH)2] (7), where bmmpa, 8Q, 2ampy, pydcH2 are 5-bromo-6-methyl-2-morpholinepyrimidine-4- amine, 8-hydroxyquinoline, 2-amino-6-methylpyridine, and pyridine-2,6- dicarboxylic acid, respectively, have been synthesized and structurally characterized by elemental analyses, infrared, UV spectroscopic methods, and X-ray crystallography. Metal ions of 1 and 5 are six-coordinate with distorted octahedral geometries. Compound 1 is an anionic mononuclear complex and 5 is a binuclear compound constructed from cationic and anionic parts. The crystal data of 5 reveal that the cationic part is formed by five terminal waters and one μ-carboxylate oxygen O2 from the anionic portion and the anionic complex is built from two deprotonated (pydc)2- moieties. In the compounds, pydcH2 is tridentate by one nitrogen of pyridine ring and two oxygens of carboxylate.
Electrophilic ipso-substitution in uracil derivatives
Chernikova,Khursan,Spirikhin,Yunusov
, p. 2445 - 2453 (2014/11/07)
Treatment of 5-iodo-1,3,6-trimethyluracil with 50% H2SO 4 gives 1,3,6-trimethyluracil; with 5-bromo-1,3,6-trimethyluracil, a mixture of 1,3,6-trimethyluracil and 6-bromomethyl-1,3-dimethyluracil is obtained. 5-Chloro-1,3,6-trimethyluracil remains inert under these conditions. According to the DFT modeling of the reactions of 5-halo-1,3,6-trimethyluracils, a nucleophilic agent can abstract either Hal+ or the methyl proton from the carbocation formed by protonation of the starting halouracil at position 5, which accounts for the formation of two products from the 5-bromo derivative. Under similar conditions, 6-methyluracil dibromohydrin yields N-bromo-5-bromo-6-hydroxymethyluracil. Bromination or chlorination of 5-hydroxymethyl- or 5-formyl-6-methyluracils follows the ipso-substitution scheme leading to 6-methyluracil 5-halo- and 5,5-dihalohydrins.
Oxidative halogenation of 6-methyluracil
Kasradze,Ignatyeva,Khusnutdinov,Suponitskii, K. Yu.,Antipin, M. Yu.,Yunusov
, p. 1018 - 1027 (2013/03/13)
An efficient method has been developed for the preparation of halo derivatives of 6-methyluracil by employing oxidative halogenation. Elemental halogens and potassium halides were used as the halogenating agents, while NaNO3 and H2O2 were used as the oxidizing agents. Iodination of 6-methyl-uracil leads to 5-iodo-6-methyluracil as the single reaction product, while bromination or chlorination lead to 5-halo-6-methyluracil, 5,5-dihalo-6-hydroxy-6-methyl-5,6-dihydrouracil, or their mixture depending on the acidity of the medium and the ratio of the substrate and reagents. Bromination of 5-chloro-6-methyluracil leads to 5-bromo-5-chloro-6-hydroxy-6-methyl-5,6-dihydrouracil, while chlorination of 6-methyl-, 5-bromo-6-methyl-, and 5-chloro-6-methyluracils using gaseous chlorine yields 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil.