Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles

Pokhodylo, Nazariy T.; Tupychak, M.; Обушак, Н. Д.

doi:10.1134/s1070428022020087

Cited by 2 publications

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References 44 publications

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“…In the 13 Also, evidence of the dominance of the open form is indirectly indicated by the fact that when the compound is heated to 175 • C, its decomposition process is very similar to decarboxylation, which is characteristic of 1,2,3-triazole-4-carboxylic acids [15]. Also, evidence of the dominance of the open form is indirectly indicated by the fact that when the compound is heated to 175 °C, its decomposition process is very similar to decarboxylation, which is characteristic of 1,2,3-triazole-4-carboxylic acids [15].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series

Pokhodylo¹,

Обушак²

2022

Molbank

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Synthesis of the first representative of a 5-formyl-1H-1,2,3-triazole-4-carboxylic acids series – 1-(4-ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic acid was performed. The 1-azido-4-ethoxybenzene was chosen as a starting reagent in a two-step synthesis, which reacted with the ethyl 4,4-diethoxy-3-oxobutanoate under base catalysis to form ethyl 5-(diethoxymethyl)-1-(4-ethoxyphenyl)-1H-1,2,3-triazole-4-carboxylate with protected formyl and acid groups. By the subsequent saponification of the ester group and removing of acetal protection, the target 1-(4-ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic acid was obtained. It has been found that the free acid form predominated in the solution under its cyclic 6-hydroxy-1,6-dihydro-4H-furo[3,4-d][1,2,3]triazol-4-one tautomer. According to 1H NMR, cyclic hemiacetal is about 20%.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series

Pokhodylo¹,

Обушак²

2022

Molbank

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“…Obushak et al found that the reaction of aryl azides with phosphorus ketoylides was a convenient method for the synthesis of 1,5-disubstituted 1,2,3-triazoles ( Scheme 42 ) [ 65 ]. The 1,5-disubstituted 1,2,3-triazoles could be obtained by eliminating phosphorus-containing compounds in near quantitative yields.…”

Section: Formal 15-selective Click Reaction Of Azide With Alkynementioning

confidence: 99%

Overview of 1,5-Selective Click Reaction of Azides with Alkynes or Their Synthetic Equivalents

et al. 2023

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Nowadays, the click reaction of azides with alkynes has evolved rapidly and become one of the most efficient methods to synthesize 1,2,3-triazoles, which are an important class of N-containing heterocycles. While the 1,4-selective click reaction of azides with alkynes is well established to synthesize 1,4-substituted 1,2,3-triazoles, the corresponding 1,5-selective click reaction for the generation of 1,5-substituted-1,2,3-triazoles is much less explored, and there is no systematic review for the 1,5-selective click reaction. This timely review summarizes the discovery and development of 1,5-selective click reactions of azides with alkynes for the synthesis of 1,5-substituted 1,2,3-triazoles. The 1,5-selective click reactions will be divided into three types according to the critical reactive intermediates: metallacyclic intermediates, acetylide intermediate, and formal 1,5-selective azide-alkyne cycloaddition. The related mechanistic studies will also be involved in this review.

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Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles

Cited by 2 publications

References 44 publications

Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series

Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series

Overview of 1,5-Selective Click Reaction of Azides with Alkynes or Their Synthetic Equivalents

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