M. Wanner, J. Hageman, G. Koomen
1978
Citations
0
Influential Citations
7
Citations
Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
Treatment of 6-chloro-9-(tetrahydro-2-pyranyl)purine (8) with 2 equivalents of methylene triphenylphosphorane (−30°) yields the corresponding purinyl ylide 9. Reaction of the latter with ethyl glyoxylate gives the expected acrylic ester derivative 10. Ethyl (dimethylsulfuranylidene)acetate adds to the acrylic ester moiety to form a mixture of isomeric purinyl substituted cyclopropanedicarboxylic esters (11a and 12a). The ylide 9 reacts with cis-dimethyl epoxysuccinate (13) to give the oxaphospholane derivative 14, which undergoes ring opening (DMSO, 80°) to 6-[2,3-(diethoxycarbonyl)-1-propenyl]-9-(tetrahydro-2-pyranyl)purine (15). Hydrogenation (H2/Pd) of 15 leads to the corresponding propyl derivative 17; while its treatment with base (NaH/DME) produces the tricyclic product 16. The significance of purinyl derivatives 16 and 17 (R = H) as potential inhibitors in the biosynthesis of adenosine monophosphate (AMP, 3) is discussed.