Ferrocenoyl-adenines: substituent effects on regioselective acylation.

ABSTRACT: A series of N ⁶-substituted adenine-ferrocene conjugates was prepared and the reaction mechanism underlying the synthesis was explored. The S_N2-like reaction between ferrocenoyl chloride and adenine anions is a regioselective process in which the product ratio (N7/N9-ferrocenoyl isomers) is governed by the steric property of the substituent at the N ⁶-position. Steric effects were evaluated by using Charton (empirical) and Sterimol (computational) parameters. The bulky substituents may shield the proximal N7 region of space, which prevents the approach of an electrophile towards the N7 atom. As a consequence, the formation of N7-isomer is a kinetically less feasible process, i.e., the corresponding transition

SUBMITTER: Toma M 

PROVIDER: S-EPMC9520867 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature