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Reactions of 3-Benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (2-Methylquinazoline Reissert Compound) with Acid, Base, Sodium Hydride, and Electrophiles
Acid hydrolysis of 3-benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (11, 2-methylquinazoline Reissert compound) resulted in the formation of the oxazole (13).Alkaline hydrolysis gave 2-methylquinazoline (12) and banzoic acid (8).The anion (D1), generated from 11 and NaH in dimethylformamide (DMF), underwent decomposition to give the ketone (14) and the cyanoquinazoline (15) together with by-products 12 and O-benzoylbenzoin (9).Compound 11 reacted with aromatic aldehydes (10a-c) in the presence of NaH to give the benzoates (16a-c) and by-products 12 and 15.Alkylation (or arylation) with alkyl (or aryl) halides (11a, b) afforded the corresponding 4-substituted derivatives (19a, b) and a by-product 14.The reactivities of 11 and 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile (21, quinazoline Reissert compound) are compared. Keywords—Reissert compound; quinazoline; hydrolysis; Reissert compound anion; rearrengement; aromatization; electronic effect; electrophilic substitution
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Reference£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem