- One-pot synthesis of azanucleosides from proline derivatives stereoselectivity in sequential processes
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Common amino acid derivatives can be transformed in onestep fashion into N-azanucleosides. The method is a sequential process initiated, by a domino radical decarboxylation/ oxidation reaction; an acyliminium ion is formed as an intermediate and can be trapped by nitrogen bases (purines, pyrimidines, and benzotriazole). The mildness of the reaction conditions and the good, yields obtained make this procedure an interesting alternative to the conventional processes. Good stereoselectivities were obtained with 4-(silyloxy)proline derivatives as substrates.
- Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo
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experimental part
p. 3847 - 3857
(2010/09/05)
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- One-pot synthesis of acyclic nucleosides from carbohydrate derivatives, by combination of tandem and sequential reactions
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(Chemical Equation Presented) The design of processes which combine tandem and sequential reactions allows the transformation of readily available precursors into high-profit products. This strategy is illustrated by the one-pot synthesis of acyclic nucle
- Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo,Alvarez, Eleuterio
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p. 9523 - 9532
(2008/03/28)
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- Chemistry of N,N-bis(silyloxy)enamines: Part 5 - Interaction with N-trialkylsilylated azoles. Convenient method for the synthesis of α-azolyl-substituted oximes
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Aliphatic nitro compounds can be considered as good precursors of a wide variety of α-azolyl-substituted oximes. The double silylation of convenient aliphatic nitro compounds and the subsequent N,C-coupling of the resulting N,N-bis(silyloxy)enamines 3 with N-silylated azoles 4 lead to the formation of the silylated α-azolylsubstituted oximes 6, which can be smoothly desilylated to give the target α-azolyl-substituted oximes 5. The mechanism of the key step of this process - N,C-coupling - includes the generation of corresponding conjugated nitrosoalkenes 7 (Schemes 4 and 5). The contribution of the chain mechanism in the overall process is considered as well, The studies of the scope and limitations of this reaction, as well as the optimization of its conditions were accomplished. The configuration of the C=N bond in oximes was established by NMR.
- Lesiv, Alexey V.,Ioffe, Sema L.,Strelenko, Yury A.,Tartakovsky, Vladimir A.
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p. 3489 - 3507
(2007/10/03)
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- Acyclic Analogs of Nucleosides. Synthesis of Hydroxyalkylbenzimidazoles and -Benzotriazoles
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Condensation of trimethylsilyl derivatives of benzimidazole and benzotriazole with alkylating agents in the presence of trimethylsilyl trifluoromethanesulfonate or SnCl4, or direct alkylation of the sodium salts of benzimidazole and benzotriazole, gives 1-(2,3-dihydroxypropyl)-, 1-(3-hydroxy-2-oxabutyl)-, 1-(3-hydroxymethyl-4-hydroxy-2-oxabutyl)-, and 1-(1,5-dihydroxy-3-oxapent-2-yl)benzimidazole and -benzotriazole.
- Yavorskii, A. E.,Stetsenko, A. V.,Zavgorodnii, S. G.,Florent'ev, V. L.
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p. 163 - 167
(2007/10/02)
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