On the Reaction of 4-Quinazolinecarbonitrile with Nucleophilic Reagents. II. Reaction of 4-Quinazolinecarbonitrile with Grignard Reagents
1962 年 10 巻 11 号 p. 1043-1047
詳細
1962 年 10 巻 11 号 p. 1043-1047
Grignard reagents reacted as anionoid with 4-quinazolinecarbonitrile (I).
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.
The mechanism for these reactions may be suggested as in Chart 2.
Reactions of 4-chloroquinazoline (VII) with Grignard reagents were carried out in order to compare them with those of (I) using the same reagents.
(VII), with isopropylmagnesium bromide, afforded (W) and 4, 4'-biquinazoline (VIII), with phenylmagnesium bromide, (VIII), and with benzylmagnesium chloride, (VI).
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).
