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1980•Bulletin of the Chemical Society of JapanRequires access

Studies on the Tautomerism of 2-Anilinopyridine and Related Heterocycles. II. 2-Anilino-5-nitropyridine and 2-Anilinopyrimidine

Minoru Hirota, Toshiyuki Sekiya, Akira Hishikura, Hiroko Endo, Yoshiki Hamada, Yoshio Ito

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Abstract

Abstract The tautomeric behavior of 5-nitro-2-anilinopyridine and 2-anilinopyrimidine was studied. 2-(N-Methylanilino) and l-methyl-2-(phenylimino)-1,2-dihydro derivatives were prepared as models for the amino and imino tautomers, respectively, and their spectra were compared. The results and the assumed tautomeric equilibrium constants strongly suggest the equilibria to be favorable to the amino tautomers, the Kt values being considerably smaller than that of the parent 2-anilinopyridine.

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Abstract The tautomeric behavior of 5-nitro-2-anilinopyridine and 2-anilinopyrimidine was studied. 2-(N-Methylanilino) and l-methyl-2-(phenylimino)-1,2-dihydro derivatives were prepared as models for the amino and imino tautomers, respectively, and their spectra were compared. The results and the assumed tautomeric equilibrium constants strongly suggest the equilibria to be favorable to the amino tautomers, the Kt values being considerably smaller than that of the parent 2-anilinopyridine.

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Available abstract

Abstract The tautomeric behavior of 5-nitro-2-anilinopyridine and 2-anilinopyrimidine was studied. 2-(N-Methylanilino) and l-methyl-2-(phenylimino)-1,2-dihydro derivatives were prepared as models for the amino and imino tautomers, respectively, and their spectra were compared. The results and the assumed tautomeric equilibrium constants strongly suggest the equilibria to be favorable to the amino tautomers, the Kt values being considerably smaller than that of the parent 2-anilinopyridine.

Key concepts: Tautomer, Chemistry, Medicinal chemistry, Computational chemistry, Stereochemistry

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Studies on the Tautomerism of 2-Anilinopyridine and Related Heterocycles. II. 2-Anilino-5-nitropyridine and 2-Anilinopyrimidine — Research Paper | ScholarLens