On the Reaction of 4-Quinazolinecabonitrile with Nucleophilic Reagents. IV. Reaction of 4-Quinazolinecarbonitrile with Active Methylene Compounds

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The reactions of 4-quinazolinecarbonitrile (I) with active methylene compounds were carried out in order to elucidate the chemical properties of (I). In the presence of sodium amide, reactions of (I) with ethyl acetoacetate, diethyl malonate, or ethyl cyanoacetate give ethyl 4-quinazolineacetate (II), and ethyl α-cyano-4-quinazolineacetate (III), respectively. In the presence of potassium carbonate, reactions of (I) with nitromethane, or nitroethane give 4-nitromethylquinazoline (IV), and 4-(1-nitroethyl) quinazoline (V), respectively. The foregoing results showed that the 4-position of (I) was very reactive to anionoid reagents, as was already demonstrated in Parts I, II, and III of this series.

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