Alkylation of 9-substituted guanine derivatives with [alpha],[omega]-dihaloalkanes

Alkylation of 9-substituted guanine derivatives with [alpha],[omega]-dihaloalkanes

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-...

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Veröffentlicht in:Heteroatom chemistry 2017-09, Vol.28 (5)
Hauptverfasser: Framski, Grzegorz, Goslinski, Tomasz, Januszczyk, Piotr, Golankiewicz, Bozenna, Ostrowski, Tomasz
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Alkylation
Derivatives
Dimers
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container_issue 5
container_start_page
container_title Heteroatom chemistry
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creator Framski, Grzegorz
Goslinski, Tomasz
Januszczyk, Piotr
Golankiewicz, Bozenna
Ostrowski, Tomasz
description 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 [alpha],[omega]-dibromoalkanes, or [alpha]-bromo-[omega]-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.
doi_str_mv 10.1002/hc.21399
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subjects Alkylation
Derivatives
Dimers
title Alkylation of 9-substituted guanine derivatives with [alpha],[omega]-dihaloalkanes
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