Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3, 4-dihydro-4-quinazolinecarbonitrile) with Electrophiles

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Reactions of the quinazoline Reissert compound (2) with various electrophiles in the presence of sodium hydride in N, N-dimethylformamide were investigated. The reactions with aldehydes (3) and ketones (12) gave α-aryl (or alkyl)-(7) and α-alkyl-α-aryl (or alkyl)-4-quinazolinylmethyl benzoates (16), respectively. The reaction with π-deficient heteroaromatics (10a-c) gave 4-heteroarylquinazolines (20a-c). Alkylation (or arylation) with alkyl (or aryl) halides (23a-c) afforded 4-substituted 3-benzoyl-3, 4-dihydro-4-quinazolinecarbonitriles (24a-c). The reaction with dimethyl acetylenedicarboxylate proceeded in two ways, giving dimethyl 3-phenylpyrrolo [1, 2-c] quinazoline-1, 2-dicarboxylate (27) and dimethyl 3-benzoyl-4-cyano-1, 2, 3, 4-tetrahydro-2, 4-ethenoquinazoline-9, 10-dicarboxylate (28). The reaction with 2-alkenonitriles (29a, b) resulted in the formation of 2-benzoyl-3-(4-quinanolinyl) alkanonitriles (32a, b).