Alkylation of 9-substituted guanine derivatives with α,ω-dihaloalkanes

Abstract

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.

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