A novel one-pot synthesis method of 3,4,5-triaryl-substituted 1,2,4-triazoles

Yakuschenko, Igor K.; Pozdeeva, N. N.; Gadomsky, S. Ya.

doi:10.1007/s10593-019-02545-y

Cited by 6 publications

(5 citation statements)

References 19 publications

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“…Polyphosphate ester (PPE) is a known mild reagent for cyclo-dehydration reactions [21,22], and it can be used even without additional protection of the phenol groups [21]. Here we report for the first time the usage of PPE as the dehydration additive for imidization reaction.…”

Section: Resultsmentioning

confidence: 98%

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

Tretyakov¹,

Gadomsky²,

Terentiev³

2023

Preprint

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We describe a new reaction for the synthesis of compounds with a hydroxylamide group (hydroxamic acids) which are widely known for their biological activity (histone deacetylase inhibitors, matrix metalloproteinases inhibitors and others). The reaction involves the interaction between N-substituted succinimides and hydroxylamine in aqueous solution. A novel two step approach to the synthesis of hydroxamic acids was developed based on the new reaction. The first stage is the synthesis of N-substituted succinimide via the reaction of aromatic amine or carboxylic acid hydrazide with succinic anhydride. The second step involves the imide ring opening reaction in the presence of hydroxylamine. For the both stages, universal synthetic methods have been developed that exclude additional purification stages for the target compounds. Sixteen hydroxamic acids were synthesized using the developed approach. Most of the compounds were obtained for the first time.

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Section: Resultsmentioning

confidence: 98%

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

Tretyakov¹,

Gadomsky²,

Terentiev³

2023

Preprint

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“…Therefore, we hypothesize that thermal imidization is not universal for N-substituted succinimides synthesis, especially for compounds with less thermal stability than 4-anilino-4-oxobutanoic acid. Using acetic anhydride can result in a side acetylation reaction (e.g., the reaction with phenol groups [32,33]).…”

Section: Resultsmentioning

confidence: 99%

A Reaction of N-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

2023

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We describe a novel two-step approach for the synthesis of compounds with a hydroxyl-amide group (hydroxamic acids), which are widely known for their biological activity (histone deacetylase inhibitors, matrix metalloproteinases inhibitors and others). The first stage is the synthesis of N-substituted succinimide via the reaction of aromatic amine or carboxylic acid hydrazide with succinic anhydride. The second step involves the imide ring opening reaction by hydroxylamine. For both stages, universal synthetic methods are developed to exclude additional purification procedures for the target compounds. Sixteen hydroxamic acids are synthesized using the developed approach. Most of the compounds are obtained for the first time.

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“…We also found that chloroform is a convenient dilution solvent for the reaction since its insertion which gives a homogeneous reaction mixture and simplifies temperature control. The latter is very important since the temperature for the reactions using PPE must be below 85 °C [ 19 ]. Table 1 presents the results of the approach developed for 2-amino-1,3,4-thiadiazole synthesis based on Scheme 1 .…”

Section: Resultsmentioning

confidence: 99%

“…Thus, the development of cost-efficient and safe one-pot methods for 2-amino-1,3,4-thiadiazoles synthesis remains relevant. It was shown recently that polyphosphate ester (PPE) is suitable for the synthesis of five-membered nitrogen-containing heterocyclic structures under mild conditions at a temperature not higher than 85 °C [ 19 ]. Based on the general concept of the reaction mechanism of PPE [ 19 ], one might expect that this reagent might also be used to carry out the reaction depicted in Scheme 1 .…”

Section: Introductionmentioning

confidence: 99%

“…It was shown recently that polyphosphate ester (PPE) is suitable for the synthesis of five-membered nitrogen-containing heterocyclic structures under mild conditions at a temperature not higher than 85 °C [ 19 ]. Based on the general concept of the reaction mechanism of PPE [ 19 ], one might expect that this reagent might also be used to carry out the reaction depicted in Scheme 1 . In this regard, our work aimed at investigating the reaction between thiosemicarbazide and different carboxylic acids in the presence of PPE as a new approach to a 2-amino-1,3,4-thiadiazole one-pot synthesis.…”

Section: Introductionmentioning

confidence: 99%

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A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives

et al. 2021

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The main purpose of the study was the development of a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl3 or SOCl2. The reaction was investigated in the presence of polyphosphate ester (PPE). It was found that, in the presence of PPE, the reaction between the thiosemicarbazide and carboxylic acid proceeds in one-pot through three steps with the formation of corresponding 2-amino-1,3,4-thiadiazole. Using the developed approach five, 2-amino-1,3,4-thiadiazoles were synthesized. The structures of all compounds were proven by mass spectrometry, IR, and NMR spectroscopies.

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A novel one-pot synthesis method of 3,4,5-triaryl-substituted 1,2,4-triazoles

Cited by 6 publications

References 19 publications

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

A Reaction of N-substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

A Reaction of N-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids

A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives

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