Structural revision in the reactions of 3-cyanochromones with primary aromatic amines. Improved synthesis of 2-amino-3-(aryliminomethyl)chromones

✍ Scribed by Vyacheslav Ya. Sosnovskikh; Vladimir S. Moshkin; Mikhail I. Kodess

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 247 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.09.028

✦ Synopsis

3-(aryl/ alkylimino)methylchromones 3-Anilino-2-salicyloylacrylonitriles a b s t r a c t 3-Cyanochromones react with primary aromatic amines to give 2-amino-3-(aryliminomethyl)chromones as the sole products or as their mixtures with Z-and E-3-anilino-2-salicyloylacrylonitriles, depending on the reaction conditions. With aliphatic amines, 2-amino-3-(alkyliminomethyl)chromones are obtained in good yields. The reaction of 3-cyanochromone with o-phenylenediamine is reinvestigated and proof for the product structure and a possible reaction pathway are presented.