Alkylation of some 6-substituted purines under interphase catalysis conditions |
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Authors: | N P Ramzaeva I N Goncharova M Yu Lidak Yu Sh Gol'dberg M V Shimanskaya |
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Institution: | (1) Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006 Riga |
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Abstract: | The mixture of 9-, 3-, and 7-benzyl-6-substituted purines is formed in almost quantitative yield by the alkylation of 6-benzylamino-, 6-furfurylamino-, 6-methylthio-, and 6-chloropurine with benzyl halides in the biphasic system of the liquid-liquid or liquid-solid type in the presence of interphase catalysts (quaternary ammonium salts, 18-crown-6). The catalytic activity of the quaternary ammonium salts increases with the increase in the lipophilicity of the cation. Taking the alkylation of 6-benzylaminopurine as an example, the possibility of the application of triphasic catalysis in the alkylation reaction of purines is indicated. The alkylation of 6-substituted purines with isopropyl bromide proceeds regioselectively under the conditions of the interphase catalysis with the formation of the corresponding 9-isopropylpurines.For the preliminary communication, see 1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 113–118, January, 1987. |
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