ChemInform Abstract: An Efficient Route to Ethyl 5‐Alkyl‐ (Aryl)‐1H‐1,2,4‐triazole‐3‐carboxylates.

Chudinov, M. V.; Matveev, A. V.; Zhurilo, Nikolay; Prutkov, Alexander N.; Швец, В. И.

doi:10.1002/chin.201608151

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“…Первый [33] дает возможность параллельного синтеза ряда соединений из единого предшественника β-N-Boc-оксаламидразона (a), (где Boc -трет-бутилоксикарбонильная защитная группа), но имеет недостаток -относительно низкие выходы целевых соединений. Второй [34] позволяет получать 5-замещенные 1,2,4-триазол-3-карбоновые кислоты с высокими выходами, но требует получения индивидуальных синтетических предшественников для каждого целевого соединения, что увеличивает время проведения эксперимента [35]. В итоге, для решения задачи комбинаторного синтеза, нами был выбран именно параллельный способ получения производных 1,2,4-триазол-3-карбоновых кислот c (метод I на схеме 1).…”

Section: результаты и их обсуждениеunclassified

Synthesis of 5-oxymethyl-1,2,4-triazole-3-carboxamides

Grebenkina

Prutkov

Matveev

et al. 2022

Fine Chem. Technol.

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Objectives. A key step in the synthesis of natural nucleoside analogs is the formation of a glycosidic bond between the carbohydrate fragment and the heterocyclic base. Glycosylation methods differ in terms of regio- and stereoselectivity. A promising method for the highly specific synthesis of new pharmacologically active compounds involves an enzymatic reaction catalyzed by genetically engineered nucleoside phosphorylases. This study is devoted to the synthesis of a library of analogs of nucleoside heterocyclic bases—5-oxymethyl-1,2,4-triazole- 3-carboxamides—in order to investigate the substrate specificity of genetically engineered nucleoside phosphorylases.Methods. A method of cyclization of acylamidrazones obtained from the single synthetic precursor β-N-tert-butyloxycarbonyl-oxalamidrazone was used to parallel-synthesize new 5-alkoxy/ aryloxymethyl-1,2,4-triazole-3-carboxamides. Silica gel column chromatography was used to isolate and purify the synthesized compounds. A complex of physicochemical analysis methods (nuclear magnetic resonance spectroscopy, chromatography, and mass spectrometry) confirmed the structure of the compounds obtained in the work.Results. 5-alkoxy/aryloxymethyl-1,2,4-triazole-3-carboxamides were obtained to study the substrate specificity of genetically engineered nucleoside phosphorylases. The possibility of obtaining new nucleoside analogs by the chemico-enzymatic method was demonstrated on the basis of preliminary assessment results.Conclusions. The physicochemical characteristics of a series of novel 5-alkoxy/aryloxymethyl- 1,2,4-triazole-3-carboxamides were studied along with their potential to act as substrates for the transglycosylation reaction catalyzed by nucleoside phosphorylases.

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Section: результаты и их обсуждениеunclassified