On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. II. Reaction of 4-Quinazolinecarbonitrile with Grignard Reagents

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Grignard reagents reacted as anionoid with 4-quinazolinecarbonitrile (I).<BR>Reaction of (I) with methylmagnesium iodide, ethylmagnesium bromide, isopropylmagnesium bromide, phenylmagnesium bromide, and benzylmagnesium chloride afforded 4-methyl-(II), 4-ethyl-(III), 4-isopropyl-(IV), 4-phenyl-(V), and 4-benzylquinazoline-(VI), respectively.<BR>The mechanism for these reactions may be suggested as in Chart 2.<BR>Reactions of 4-chloroquinazoline (VII) with Grignard reagents were carried out in order to compare them with those of (I) using the same reagents.<BR>(VII), with isopropylmagnesium bromide, afforded (W) and 4, 4'-biquinazoline (VIII), with phenylmagnesium bromide, (VIII), and with benzylmagnesium chloride, (VI).<BR>The foregoing results showed that the 4-position in (I) was very reactive to anionoid reagents, and some differences in chemical properties existed between (VIII) and (I).

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