title: Synthesis of 2-aminoquinoline-3-carboamides and pyrimido[4,5-b]quinolin-4-ones through copper-catalyzed one-pot multicomponent reactions.
abstract: Pyrimido[4,5-b]quinolinones have attracted considerable interest from both chemical and medicinal scientists as these compounds display remarkable antimicrobial, anti-inflammatory, antitumor, antiallergy, analgesic, and antioxidant activities. The importance of pyrimido[4,5-b]quinolinones has stimulated enormous efforts to develop efficient methodologies for their synthesis. Herein, we disclose a novel synthetic protocol toward pyrimido[4,5-b]quinolin-4-ones through Cu(OAc)2 -catalyzed one-pot four-component reactions of 2-bromobenzaldehydes, aqueous ammonia, cyanoacetamides and aldehydes. The synthetic procedure combines amination/condensation/cyclization/dehydrogenation reactions in one pot, allowing synthesis of complex compounds in a simple and practical manner. Compared with literature procedures, the synthetic strategies developed herein showed advantages such as readily available and economically sustainable starting materials, structural diversity of products, good functional group tolerance, and a remarkably simple operation process.
authors.affiliation: School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, 46 Jianshe Road, Xinxiang, Henan 453007 (P. R. China), Fax: (+86) 373-332-6336. xinyingzhang@htu.cn.
authors.forename: Xin-Ying
authors.initials: XY
authors.lastname: Zhang
authors.forename: Xiao-Jie
authors.initials: XJ
authors.lastname: Guo
authors.forename: Xue-Sen
authors.initials: XS
authors.lastname: Fan
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D000634:Aminoquinolines / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D009570:Nitriles / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000577:Amides; D000634:Aminoquinolines; D009570:Nitriles; D015363:Quinolones; D000641:Ammonia; D003300:Copper; C031594:2-cyanoacetamide
keywords: 2-aminoquinoline-3-carboamides; copper catalysis; multicomponent reactions; one-pot reactions; pyrimido-[4,5-b]quinolin-4-ones