Quinazolineに対するアニオノイド試薬の反応

抄録

The 2- or 4-position of quinazoline is expected to be active to anionoid reagent. In fact, reaction of quinazoline with several anionoid reagents showed that the 4-position of quinazoline is extremely reactive. The reaction of quinazoline with sodium amide, Grignard reagent, phenyllithium, hydrogen cyanide, sodium hydrogensulfite, sulfurous acid, and hydrazine respectively afforded 4-aminoquinazoline (I), 4-methyl-3, 4-dihydroquinazoline (III), 4-phenyl-3, 4-dihydroquinazoline (VI), quinazoline-4-carbonitrile (VII), 3, 4-dihydroquinazoline-4-carbonitrile (X), 3, 4-dihydroquin-azoline-4-sulfonic acid (XII), and 4-hydrazinoquinazoline (XIII).
The preparation of the starting quinazoline was made by the modified method. 4-Quinazolone was derived to the chloro compound, which was purified by passing through alumina column, and submitted to catalytic reduction in neutral medium, at ordinary temperature and pressure, using a catalyst of palladium on magnesium oxide carrier, affording quinazoline in a high yield.