Reactions of 9-substituted guanine derivatives with NaH/1,2-dibromoethane, 1,3-dibromopropane, or 1,4-dibromobutane at room temperature resulted in the isolation of tricyclic 1,N2-(1,2-ethano)guanine, 1,N2-(1,3-propano)guanine, or 1,N2-(1,4-butano)guanine products, respectively. O6-Haloalkyl and N1-haloalkyl products were obtained following the use of NaH/1,4-dibromobutane, higher α,ω-dibromoalkanes, or α-bromo-ω-fluoroalkanes. Raising the reaction temperature opened the synthetic way toward O6-guanine-alkylene-O6-guanine and N1-guanine-alkylene-O6-guanine symmetric and unsymmetric dimers. Protection of the substrate amine group to form N,N-dialkylformamidine provided the access to N1-guanine-alkylene-N1-guanine dimers.

中文翻译：

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9-取代鸟嘌呤衍生物与 α,ω-二卤代烷烃的烷基化

9-取代鸟嘌呤衍生物与 NaH/1,2-二溴乙烷、1,3-二溴丙烷或 1,4-二溴丁烷在室温下的反应导致三环 1,N2-(1,2-乙醇)鸟嘌呤的分离，分别为 1,N2-(1,3-丙烷)鸟嘌呤或 1,N2-(1,4-丁烷)鸟嘌呤产品。使用 NaH/1,4-二溴丁烷、高级 α,ω-二溴烷烃或 α-溴-ω-氟烷烃后，得到 O6-卤代烷基和 N1-卤代烷基产物。提高反应温度为 O6-鸟嘌呤-亚烷基-O6-鸟嘌呤和 N1-鸟嘌呤-亚烷基-O6-鸟嘌呤对称和不对称二聚体的合成开辟了道路。保护底物胺基以形成 N,N-二烷基甲脒提供了获得 N1-鸟嘌呤-亚烷基-N1-鸟嘌呤二聚体的途径。