New Approach to the Synthesis of  N  7 ‐Arylguanines and  N  7 ‐Aryladenines | Zendy

Keder Roman | Zendy; Dvořáková Hana | Zendy; Dvořák Dalimil | Zendy

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New Approach to the Synthesis of N 7 ‐Arylguanines and N 7 ‐Aryladenines

Author(s) -

Keder Roman,

Dvořáková Hana,

Dvořák Dalimil

Publication year - 2009

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.200801002

Subject(s) - chemistry , dichloromethane , hydrolysis , aryl , methanol , ligand (biochemistry) , medicinal chemistry , copper , base (topology) , stereochemistry , organic chemistry , solvent , receptor , mathematical analysis , biochemistry , alkyl , mathematics

The copper‐mediated arylation of 7‐methylpyrimido[1,2‐ a ]purin‐10(3 H )‐one ( 1 ) in dichloromethane or of N 2 ‐(dimethylamino)methyleneguanine ( 2 ) in methanol in the presence of TMEDA as a base/ligand led to the preferential formation of 1‐aryl‐7‐methylpyrimido[1,2‐ a ]purin‐10(3 H )‐ones ( 4 ) and 7‐aryl‐ N 2 ‐(dimethylamino)methyleneguanines ( 7 ), respectively. These compounds can be easily hydrolysed to the corresponding 7‐arylguanines. Similar arylation of N 6 ‐(dimethylamino)methyleneadenine ( 15 ) in the presence of o ‐phenanthroline instead of TMEDA afforded mainly 7‐aryladenines after hydrolysis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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