3-Oxy-5-phenyl-1H-1,2,3-triazole-4-carboxylic Acid. Synthesis, Structure, and Properties

Autor:	Ch. Nather, I. V. Tselinskii, S. F. Mel'nikova, S. D. Shaposhnikov, Tim Traulsen, Willy Friedrichsen, O. V. Shtabova
Rok vydání:	2005
Předmět:	1 2 3-Triazole Organic Chemistry Alkylation Chloride Medicinal chemistry Crystal chemistry.chemical_compound chemistry Nitration medicine Organic chemistry Hydrate Derivative (chemistry) Methyl iodide medicine.drug
Zdroj:	Russian Journal of Organic Chemistry. 41:591-598
ISSN:	1608-3393 1070-4280
DOI:	10.1007/s11178-005-0209-8
Popis:	The structure of 3-oxy-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid was determined both experimentally (by the X-ray diffraction method) and by quantum-chemical calculations. Alkylation of 3-oxy-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid (as crystal hydrate) with methyl iodide, depending on the reactant ratio, gives 1-methoxy-4-phenyl-1H-1,2,3-triazole-5-carboxylic acid and methyl 1-methoxy-4-phenyl-1H-1,2,3-triazole-5-carboxylate. Nitration of the title compound under mild conditions occurs at the 5-phenyl group with formation of meta-nitro derivative, while under more severe conditions 3,5-dinitrobenzoic acid is obtained. 3-Oxy-5-phenyl-1H-1,2,3-triazole-4-carboxylic acid was also converted into the corresponding acid chloride and substituted amide.
Databáze:	OpenAIRE
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