On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. III. Reaction of 4-Quinazolinecarbonitrile with Ketones

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Reactions of 4-quinazolinecarbonitrile (I) with ketones in the presence of 50% sodium hydroxide were carried out in order to elucidate the chemical properties of (I). With acetone afforded 1-(4-quinazolinyl)-2-propanone (II), with 2-butanone, 1-(4-quinazolinyl)-2-butanone (III) and 4-ethylquinazoline (IV), with 3-pentanone (IV), with 3-methyl-2-butanone, 1-(4-quinazolinyl)-3-methyl-2-butanone (V) and 4-isopropylquinazoline (VI), with acetophenone, 2-(4-quinazolinyl) acetophenone (VII), with propiophenone, (IV) and benzoic acid (VIII), w ith cyclohexanone, 4-quinazolinehexanoic acid (IX), and with cyclopentanone, 2-(4-quinazolinyl) cyclopentanone (X). The foregoing experiments showed that the 4-position in (I) was very reactive to anionoid reagents, as already demonstrated in Part I and II of this series.

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