Regioselective synthesis of two types of highly substituted 2-pyridones through similar multicomponent reactions

详细信息	查看全文 | 推荐本文 |

• 作者：Sudipta Pathak ; Ashis Kundu ; Animesh Pramanik ; ^{animesh_in2001@yahoo.co.in}
• 关键词：2-Pyridones ; Zwitterion ; Aromatic aldehyde ; Ethylcyanoacetate ; Primary diamines ; Primary monoamines ; Three component reaction ; Aerial oxidation
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：13 June, 2012
• 卷：53
• 期：24
• 页码：3030-3034
• 文件大小：2591 K

摘要

The refluxing of a mixture of ethylcyanoacetate, aromatic aldehydes, and primary monoamines in ethanol produces highly substituted 2-amino-6-pyridones such as 2-amino-1-(alkyl)-5-cyano-6-oxo-4-(aryl)-1,6-dihydropyridine-3-ethylcarboxylates in one-pot. On the other hand the refluxing of a mixture of ethylcyanoacetate, aromatic aldehydes, and primary diamines (1,2-ethylenediamine/1,3-propylenediamine) in ethanol furnishes symmetrical zwitterionic 2-pyridones such as 1-(2-amino-ethyl/3-amino-propyl)-6-hydroxy-2-oxo-4-(aryl)-1,2-dihydropyridine-3,5-dicarbonitriles. The result shows that primary diamines and monoamines react differently in the reactions, which provides new mechanistic insight into the regioselective synthesis of these biologically important compounds.