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, 20°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-dihy...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2013-12, Vol.49 (9), p.1301-1307
Main Authors: Frolov, K. A., Dotsenko, V. V., Krivokolysko, S. G.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Nitriles
Organic acids
Organic Chemistry
Pharmacy
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Summary:The reaction of cyanoselenoacetamide with a 2-anilinomethylene derivative of Meldrum’s acid (2 equiv. KOH, EtOH, 20°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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-013-1379-x