1,2,4-Triazoles. IV. Tautomerism of 3,5-Disubstituted 1,2,4-Triazoles

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概要

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• Tautomerism of ten 3,5-disubstituted 1,2,4-triazoles, which can exist in three tautomeric forms, has been studied. The nuclear magnetic resonance (NMR) and ultraviolet (UV) spectra of these 1,2,4-triazoles were compared with those of the N-methyl derivatives, which are the model compounds of the three kinds of tautomeric forms. Results indicate that a tautomeric hydrogen atom of the predominant tautomer of 3,5-disubstituted 1,2,4-triazoles is attached to the nitrogen atom at position 1 or 2 which is closer to the more electron-releasing substituents in the 3 or 5 position. For instance, 3-p-nitrophenyl-, 3-p-chlorophenyl-, and 3-γ-pyridyl-5-methylthio-1,2,4-triazole exist predominantly in the 1H form, while 3-p-aminophenyl- and 3-p-methoxyphenyl-5-methylthio-1,2,4-triazole exist predominantly in the 2H form. These results are explained in terms of the formation of cyclic dimer-type hydrogen bonds involving the N-1 and N-2 atoms of triazole rings with an exchange of a proton between the molecules. However, 5-methylthio-3-α-pyridyl-1,2,4-triazole is exceptional in existing in the 2H form, since this compound can form hydrogen bonds of another type involving the nitrogen atom of the α-pyridyl group.

• 公益社団法人日本薬学会の論文
• 1975-05-25

著者

• 久保田 晴寿

  Faculty of Pharmaceutical Sciences, University of Tokushima

• 宇多 正行

  Faculty of Pharmaceutical Sciences, University of Tokushima

• 久保田 晴寿

  徳島大学薬学部

• 久保田 晴寿

  Faculty Of Pharmaceutical Sciences University Of Tokushima

• 宇多 正行

  Faculty Of Pharmaceutical Sciences University Of Tokushima

関連論文

• Synthesis of 2-Substituted 1,3,4-Thiadiazol-5-ylacetic, Propionic, and Gltaric Acids
• Synthesis and Absolute Configuration of Optically Active 2,3-Disubstituted 2,3-Dihydro-1,3,4-thiadiazoles
• Synthesis and Uncoupling Activities of Hydrophobic Thioureas
• Synthesis of 3-Acylamino-4-hydroxymethyl-2-oxo-1-sulfoazetidines and Related Compounds
• Phenolic Components from Leaf Oil of Illicium anisatum L.
• Effect of 2,4-Dihydro-3H-1,2,4-triazole-3-thiones and Thiosemicarbazones on Iodide Uptake by the Mouse Thyroid : the Relationship between Their Structure and Anti-thyroid Activity
• 8-キノリンスルホニルクロライドとヒドラジンの反応
• オクテット
• 中日天然薬物研討会
• 2-シアノピリジンとヒドラジンの反応について
• Studies on the Synthesis of 1,3,4-Thiadiazole Derivatives. II. Synthesis of 1,3,4-Thiadiazoline-5-thiones from Amidrazones and Carbon Disulfide
• 1,3,4-Thiadiazole誘導体の合成研究(第1報) : Pyridyl-1,3,4-thiadiazole誘導体の合成について
• オクテット
• Synthesis of Novel Dihydro-1,2,4-triazoles from Thiosemicarbozones via 1,4-Diacetyl-3-methylsulfonyl-4,5-dihydro-1H-1,2,4-triazoles as Key Intermediates
• Synthesis of 2-Substituted 5-(1-Oxido-4-pyridyl)- and 5-(1-Oxido-2-pyridyl)-1,3,4-thiadiazole Derivatives by Substitution of 2-Methylsulfonyl Group with Various Nucleophiles(Organic,Chemical)
• 1,2,4-Triazoles. VIII. Synthesis and Antimicrobial Activity of 3-Alkylthio-5-pyridyl-1,2,4-triazoles and Related Compounds
• 1,2,4-Triazoles. VII. Methylation of 1,2,4-Triazoles
• 1,2,4-Triazoles. VI. Methylation of 3-Phenyl-1,2,4-triazolin-5-one, 3-Phenyl-1,2,4-triazoline-5-thione, and Their Monomethylated Derivatives
• 1,2,4-Triazoles. IV. Tautomerism of 3,5-Disubstituted 1,2,4-Triazoles
• 1,2,4-Triazoles. III. The Tautomerism of 3-Phenyl-1,2,4-triazolin-5-one, 3-Phenyl-1,2,4-triazoline-5-thione and Their N-Methyl Derivatives
• 1,2,4-Triazoles. II. The Tautomerism of 3-α-Pyridyl-1,2,4-triazoline-5-thione and Its Methyl Derivatives
• 1,2,4-Triazoles. I. Methylation of 3-α-Pyridyl-1,2,4-triazoline-5-thione

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