A site selective C-H arylation of free-(NH2) adenines with aryl chlorides: application to the synthesis of 6,8-disubstituted adenines.
An efficient site selective method for the direct arylation of free-(NH2) adenines 1 to provide a range of C-8 arylated adenines 3 in excellent yields is described. This process based on the use of Pd(OH)2/C as the catalyst and a stoichiometric amount of CuI under ligandless conditions is general. It allows the coupling to proceed with a variety of aryl halides, including for the first time cheaper and less reactive aryl chlorides. The extension of this process for the sequential preparation of non-symmetrical C8/N6-arylated adenines 4 is also reported.
Sahnoun
Sophian
S
Université Paris-Sud, CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, F-92296, France.
Messaoudi
Samir
S
Brion
Jean-Daniel
JD
Alami
Mouâd
M
D000225:Adenine / Q000138:chemical synthesis* / Q000737:chemistry*; D001665:Binding Sites; D002244:Carbon / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013379:Substrate Specificity
D002713:Chlorine; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; D000225:Adenine