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Paper | Regular issue | Vol 48, No. 6, 1998, pp.1185-1192
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8136
A Novel Synthesis of 1,6-Diamino-2-pyridones and [1,2,4]Triazolo-[1,5-a]pyridine Derivatives

Yoichi Yamada,* Heinosuke Yasuda, and Akiko Takayama

*Department of Chemistry, Faculty of Education, Utsunomiya University, 350 Mine, Utsunomiya 321-8505, Japan

Abstract

3-Cyano-1,6-diamino-2-pyridone derivatives (3) posessing various alkoxycarbonyl groups are prepared directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates (1) with cyanoacetohydrazide (2). The resulting diamine (3) (R = Et) is readily cyclized to 2-substituted [1,2,4]triazolo[1,5-a]pridine derivatives (5) in high yields by treatment with orthocarboxylic esters (4) such as trimethyl orthoformate or triethyl orthoacetate etc. Furthermore, 3-cyano-6-amino-2-pyridones (6) are although abtained in excellent yields by the reductive deamination of 3. The structural study of 6 was carried out by spectroscopic methods in some details.