Early degradation experiments on the Hydrangea alkaloid (1) indicated that this molecule was a derivative of 4-quinazolone with a side chain on the 3-position containing one basic nitrogen and two oxygens. With this limited information on hand a number of 3-alkyl-4-quinazolones with functional groups in the side chain were synthesized in order to obtain (a) suitable models for degradation experiments (l), (b) compounds to be tested for antimalarial activity,' and (e) information on the synthesis and transformations of these functional groups.2There are a number of methods described in the literature for the synthesis of molecules of this type, three of which were employed. Clark and Wagner (7) ha,ve heated primary aromatic amines with isatoic anhydride (I) and ethyl orthoformate to form 3-aryl-4-quinazolones (11). This procedure has now been 0 0 0

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The Hydrangea alkaloid (I) has been observed to form an N-carbamyl derivative (II) with potassium cyanate which cyclized to III when heated with acid (1). In order for this cyclization to take place the NH group would have to be 0Similar hydrolyses are listed in Table III under method B.

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