Abstract
Polyfunctional 4-(3-cyanopyridin-2-ylthio)acetoacetates were used in the synthesis
of 4-hydroxy-1H -thieno[2,3-b :4,5-b ]dipyridin-2-ones. The latter were used in reactions with arylidenemalononitriles
or in three-component reactions with aldehydes and malononitrile to give 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H -pyrano[2,3-d ]pyrido[3′,2′:4,5]thieno[3,2-b ]pyridines. Utilizing 4-(3-cyanopyridin-2-ylthio)acetoacetates and arylidenemalononitriles
or aldehydes and malononitrile, we developed a method for the synthesis of substituted
3-alkoxycarbonyl-6-amino-4-aryl-2-(3-cyanopyridin-2-ylthiomethyl)-4H -pyrans. Reactions of substituted 4-(3-cyanopyridin-2-ylthio)acetoacetates with hydrazine
hydrate yielded substituted 3-hydroxypyrazoles, which were further used for the preparation
of 6-amino-4-aryl-5-cyano-3-(pyrid-2-ylthiomethylene)-2,4-dihydropyrano[2,3-c ]pyrazoles. Analogously, ethyl 4-(3-cyano-1,4-dihydropyridin-2-ylthio)acetoacetates
were used for the synthesis of substituted 2-amino-4H -pyrans.
Key words
2-amino-4H -pyrans - thienopyridines - 4-(3-cyanopyridin-2-ylthio)acetoacetates - pyranopyridines
- multi-component reactions
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