HYDROLYTIC CLEAVAGE OF 6-OXOPURINES AFTER INTRAMOLECULAR ACYLATION AT N-3
Reaction of 9H-hypoxanthin-9-yl propionic acid (2c) as well as of its 6-mercapto analogue (2d) with N--N'-ethylcarbodiimide hydrochloride results in an intramolecular acylation at N-3 followed by a spontaneous hydroxylation at C-2 and opening of the pyrimidine ring.The products of these reaction sequences are the imidazopyrimidines (5c,d) which were deformylated to give the compounds 6a,b.The half-life values of the ring transformations of 2c,d as well as of its isosteres 2a,b imply that the "over-all" kinetics are 1. independent of the structure of the five-membered ring and 2. strongly effected by the 6-substituent.It is proposed that the intramolecular acylation is the rate-limiting step of the reaction cascade.
Rosemeyer, Helmut,Seela, Frank
p. 2669 - 2676
(2007/10/02)
More Articles about upstream products of 4367-64-0