Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives

The reaction of cyanoselenoacetamide with a 2-anilinomethylene derivative of Meldrum's acid (2 equiv. KOH, EtOH, 20A degrees C) gives the 5-cyano-6-hydroseleno-2-oxo-1,2-dihydropyridine-3-carboxylic acid dipotassium salt. The latter reacts with alkyl halides to yield 5-cyano-6-(R-methylseleno)-2-oxo-1,2-dihydropyridine-3-carboxylic acids. Treatment of cyanoselenoacetamide with 2-anilinomethyl derivatives of dimedone and 1,3-cyclohexanedione is accompanied by oxidation and gives 2,2'-di-selane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles). The obtained diselanes undergo cleavage using alkyl halides in KOH to give 2-(R-methylseleno)-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles or selenopheno[2,3-b]quinolines as Thorpe-Ziegler cyclization products of the latter in low yields.