1-Substituted 2′-deoxyinosine analogues

Abstract

The base 2-carbon of 2′,3′-di-O-acetyl-2′-deoxyinosine is strongly activated towards nucleophilic attack when either the 4-nitrophenyl or 2,4-dinitrophenyl group is attached to its N-1 position (product 1 or 2). 1-(ω-Aminoalkyl)- and 1-(ω-hydroxyalkyl)-2′-deoxyinosine derivatives 5, 8–10 have been efficiently synthesized by a rearrangement of the purine ring upon treatment of compound 1 or 2 with the appropriate α,ω-diamine or α,ω-hydroxyamine. Moreover 1-amino-2′-deoxyinosine 11 and 1-hydroxy-2′-deoxyinosine 13 have been easily prepared in high yields by reaction of substrate 1 or 2, respectively, with hydrazine or hydroxylamine.