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Synthesis of 5‐(functionalized acyl)‐1,3‐dialkyl‐substituted barbituric and 2‐thiobarbituric acids
Author(s) -
Zoorob Hanafi H.,
Ismail Mohamed A.,
Strekowski Lucjan
Publication year - 2001
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.5570380207
Subject(s) - chemistry , barbituric acid , tetrahydrofuran , nucleophile , pyridine , sodium methoxide , medicinal chemistry , organic chemistry , derivative (finance) , chlorine , base (topology) , intramolecular force , thiobarbituric acid , methanol , catalysis , solvent , mathematical analysis , mathematics , antioxidant , financial economics , economics , lipid peroxidation
A sodium derivative of 1,3‐dimefhylbarbituric acid or 1,3‐diethyl‐2‐thiobarbituric acid undergoes an efficient monoacylation at C5 by the reaction with ω‐chloroalkanoyl chloride or diacid dichloride in the presence of pyridine in tetrahydrofuran. A nucleophilic displacement of the chlorine in a 5‐chloroacetyl‐bartiburate can be accomplished by using a one‐pot procedure. By contrast, a similar transformation of a 5‐(chlorobutanoyl)barbituric acid requires intramolecular cyclization in the presence of a nonnucleophilic base followed by treatment with a nucleophile of the resultant 5‐[4,5‐dihydro(3 H )‐2‐furylidene]barbiturate.