Some Synthetical Experiments with 4-Quinazolone

Citation

Mirza, Rafat (1949) Some Synthetical Experiments with 4-Quinazolone. Master's thesis, California Institute of Technology. doi:10.7907/1kmx-c424. https://resolver.caltech.edu/CaltechTHESIS:06172025-224633884

Abstract

An exceedingly labile compound has been isolated by the direct acetylation of 4-quinazolone. The same compound was obtained by reacting silver acetate and 4-chlorquinazoline. Attempts to prepare 3-acetyl-4-quinaazolone by the oxidation of 3-acetyl-3, 4-dihydroquinazoline were not successful, and only 4-quinazolone was isolated as the oxidation product.

Attempts to attach the alkylaminoalkyl side chains to 4-quinazolone showed that such secondary amines undergo self condensation rather than react with 4-quinazolone. However, it was possible to introduce a dialkylaminoalkyl side chain, and 3-(diethylaminoethyl)-4-quinazolone has been synthesized and is being tested for possible antimalarial activity.

3-Acetonyl-4-quinazolone gave a well defined crystalline solid with diethylamine under the conditions of the Mannich reaction. The analysis of this compound did not agree with the values for the expected compound, and the structure has not been elucidated.

Thesis Files