Synthesis of 5‐(functionalized acyl)‐1,3‐dialkyl‐substituted barbituric and 2‐thiobarbituric acids | Zendy

Zoorob Hanafi H. | Zendy; Ismail Mohamed A. | Zendy; Strekowski Lucjan | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research