《A novel synthesis of 5-aryl-3-cyano-2-pyridones by using vinamidinium salts》.pdfVIP

Available online at Chinese Chemical Letters 20 (2009) 771–774 /locate/cclet A novel synthesis of 5-aryl-3-cyano-2-pyridones by using vinamidinium salts Xue Hui Zhang, Wu Zhong, Xing Zhou Li, Song Li * Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China Received 15 December 2008 Abstract A variety of vinamidinium salts were condensated with cyanoacetamide in refluxing methanol that contained sodium methoxide to produce 5-aryl-3-cyano-2-pyridones in good yield. Simple experimental conditions were used to prepare ten different 5-aryl-3- cyano-2-pyridones, four of which are new compounds. # 2009 Song Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. Keywords: 5-Aryl-3-cyano-2-pyridones; Vinamidinium salts; Cyclization The 2-pyridones are a class of important heteroaromatic compounds. 5-Aryl-3-cyano-2-pyridones have been prepared by the cyclization of cyanoacetamide condensated with 2-aryl-3-dimethylamino-2-propenals [1,2]. The vinamidinium salts undergo condensation reactions, similar to malonaldehyde derivatives, with bifunctional nucleophiles to form heterocycles [3]. While the vinamidinium salts have been used to prepare many different heterocycles [3] including isoxazoles, pyrazoles, pyrimidines, pyrroles [4] and thiophenes [5,6], they have not yet been used to prepare 5-aryl-3-cyano-2-pyridones. In this report, an application of 2-arylvinamidinium salts to prepare 5- aryl-3-cyano-2-pyridones is presented. The vinamidinium salts (1a–j) used i