ABSTRACT
A highly regioselective Pd-catalyzed C(Ar)-H bond activation method was developed for the modification of purines (nucleosides) with different functional groups by using purine as a directing group. This approach provides a new access to a variety of functionalized purines (nucleosides) which are potentially of great importance in medicinal chemistry.
Subject(s)
Carbon/chemistry , Hydrogen/chemistry , Palladium/chemistry , Purines/chemistry , Catalysis , Stereoisomerism , Substrate SpecificityABSTRACT
Novel C6-phosphonated purine nucleosides were obtained in good to excellent isolated yields by the simple and catalyst-free SNAr-Arbuzov reaction of trialkyl phosphite with 6-choloropurine nucleosides, including a series of nonsugar carbon nucleosides. Shorter reaction times were needed, and substantially higher yields were obtained under microwave irradiation conditions compared with conventional heating conditions.
