Synthesis of 8-amino- and 8-acetyl(benzoyl) aminomackinazolinones and their condensation with aldehydes

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From: Chemistry of Natural Compounds(Vol. 49, Issue 2)
Publisher: Springer
Document Type: Article
Length: 3,963 words
Lexile Measure: 1550L

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Abstract :

Methods for preparing of 8-nitro- and 8-aminomackinazolinones were improved. 8-Acetyl(benzoyl)aminomackinazolinones reacted smoothly with aromatic aldehydes and furfurol in glacial acetic acid to give the corresponding 4-arylidene-substituted derivatives. Reaction of 8-aminomackinazolinone with aromatic aldehydes in glacial acetic acid was accompanied by acetylation of the amine and gave 8-acetylamino-4-arylidenemackinazolinones. Reaction of 8-aminomackinazolinone and p-nitrobenzaldehyde in propionic acid produced 8-[(4'-nitrobenzylidene)amino]-4 (4"-nitrobenzylidene)mackinazolinone. In contrast, the reaction in Py occurred selectively at the amine to form the corresponding Schiff base 8-[(4'-nitrobenzylidene)amino]mackinazolinone. Keywords: mackinazolinone, aldehydes, condensation, 4-arylidene derivatives.

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Gale Document Number: GALE|A340807719