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Preparation and Crystal Structures of Purine 2,2′‐, 6,6′‐, and 8,8′‐Dimers
Author(s) -
Tobrman Tomáš,
Štěpnička Petr,
Císařová Ivana,
Dvořák Dalimil
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800017
Subject(s) - chemistry , halogenation , crystal structure , carboxylate , stacking , hydrogen bond , dimethylformamide , copper , yield (engineering) , salt (chemistry) , thiophene , purine analogue , crystallography , purine , stereochemistry , medicinal chemistry , molecule , solvent , organic chemistry , materials science , enzyme , metallurgy
Abstract Treatment of 9‐ or 7‐substituted 6‐, 2‐, or 8‐iodopurine derivatives with copper(I) thiophene‐2‐carboxylate or copper(I) 3‐methylsalicylate in N , N ‐dimethylformamide affords the corresponding 6,6′‐, 2,2′‐, and 8,8′‐purine dimers in high yield. Cross‐dimerization reactions of different iodo derivatives were attempted, but only mixtures containing the cross‐coupled products, homodimers, or dehalogenation products were obtained. The crystal structures of 9,9′‐dibenzyl‐ ( 1a ) and 9,9′‐bis(1‐methylethyl)‐9 H ,9′ H ‐[6,6′]bipurinyl ( 1c ) and the salt [ 1a H 2 ]Br 2 were determined by single‐crystal X‐ray diffraction analysis, which revealed extensive hydrogen bonding and π ··· π stacking interactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)