Synthesis of benzopyran[2,3-b]quinolinone derivatives

✍ Scribed by Guangfan Han; Bin Cui; Lizhuang Chen; Yan Jin

• Book ID: 102344082
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 213 KB
• Volume: 47
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.470

✦ Synopsis

Abstract

magnified image A series of novel 11‐amino‐3,3‐dimethyl‐8‐substituted‐12‐aryl‐3,4,7,8,9,12‐hexahydro‐2__H__‐benzopyran[2,3‐b]quinoline‐1,10‐dione derivatives 4 were synthesized by 2‐amino‐3‐cyano‐4‐aryl‐5,6,7,8‐tetrahydro‐7,7‐dimethyl‐5‐oxo‐4__H__‐benzopyran 2 with 5‐substituted‐1,3‐cyclohexanedione using p‐toluenesulfonic acid, K~2~CO~3~, and Cu~2~Cl~2~ as catalysts. The compounds 2 as easily accessible precursors were obtained from 5,5‐dimethyl‐1,3‐cyclohexanedione by Michael addition with β‐dicyanostyrenes 1, prepared by Knoevenagel condensation of different aromatic aldehydes and malononitrile. The synthesis of the title compounds 4 completed by one‐pot reaction of 4‐aryl‐4__H__‐benzopyran derivatives with 5‐substituted‐1,3‐cyclohexanediones by refluxing in toluene using TsOH as catalyst. The structures of all compounds were characterized by elemental analysis, IR, MS, and ^1^H NMR spectra. J. Heterocyclic Chem., (2010).