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N ‐acylation of 1,3‐dimethyl‐6‐aminouracils. A reversal in the regiospecificity of an electrophilic substitution induced by an intramolecular proton‐transfer
Author(s) -
Bernier JeanLuc,
HÉnichart JeanPierre,
Warin Vincent
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210440
Subject(s) - chemistry , acylation , intramolecular force , electrophile , electrophilic substitution , proton , enamine , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics
Electrophilic reactions of 1,3‐dimethyl‐6‐aminouracil lead to 5‐substituted derivatives. The introduction of a dialkylaminoalkylamino chain in the 6‐position of 1,3‐dimethyluracil modifies the regiospecificity of the acylation reaction to give N‐6 acylated compounds. This reversal in acylation is induced by an intramolecular proton‐transfer which introduces a change in the electron density of the enamine system. The cyclic transition state and the spatial conformation of the final products substantiate the proposed mechanism, on the basis of X‐ray and 1 H nmr data.