- Highly efficient, chemoselective syntheses of 2-methoxy-4-substituted pyrimidines
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Three 2-methoxy-4-substituted pyrimidine compounds were chemoselectively synthesized by diazotization, using 2,4-dichloropyrimidine as the starting material. In nonaqueous diazotization reaction system, halo-substituted 6 and 7 were efficiently prepared, and in aqueous medium, hydrolysis product 8 was afforded.
- Xu, Chunyan,Cheng, Chuanjie,Liu, Hongtao,Liu, Bo
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scheme or table
p. 545 - 548
(2012/06/01)
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- Reactions of benzonitrile oxide with methoxypyrimidines and pyrimidones
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Methoxypyrimidines preferentially add to benzonitrile oxide to give cycloadducts to their C=N double bonds. These, however, lose benzonitrile affording the corresponding pyrimidones. Cycloadditions to their C=C double bonds take place to a very low extent, and products generally undergo a ring opening process which affords the corresponding oximes. Pyrimidones preferentially give addition products to their nitrogen atoms, and only in the case of 4-pyrimidone, the cycloadduct to its C=C double bond was isolated.
- Corsaro, Antonino,Pistara, Venerando,Rescifina, Antonio,Chiacchio, Maria A.,Piperno, Anna,Romeo, Giovanni
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p. 1079 - 1097
(2007/10/03)
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- HSAB driven chemoselectivity in alkylation of uracil derivatives. A high yielding preparation of 3-alkylated and unsymmetrically 1,3-dialkylated uracils
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A qualitative hardness scale (N134) has been found for the conjugated bases of 2-methoxy-4(3H)-pyrimidinones 1-3 and applied to high yielding chemoselective N3 methylation, ethylation and benzylation reactions. Removal of the 2-methoxy group followed by a second alkylation affords unsymmetrically 1,3-disubstituted uracils.
- Gambacorta, Augusto,Farah, Mohamed Elmi,Tofani, Daniela
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p. 12615 - 12628
(2007/10/03)
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- A kinetic and nuclear magnetic resonance study of methylated pyrimidine nucleosides
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Alkylated pyrimidine nucleosides are of interest from the viewpoint of mutagenesis and carcinogenesis. (1)H and (13)C nmr data are presented for a series of 2'-deoxynucleosides methylated at the O2-, O4-, and N3-positions of the base, and discussed in terms of their physical properties.The pH dependence of the stability of the O2- and O4-methylated 2'-deoxyribosides as well as the corresponding ribosides was examined by (1)H nmr and ultraviolet (uv) spectrophotometric methods.
- Allore, B. D.,Queen, A.,Blonski, W. J.,Hruska, F. E.
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p. 2397 - 2402
(2007/10/02)
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