Microwave-assisted synthesis of 1,2,4-triazole-3-carboxamides from esters and amines under neutral conditions

Jaisankar, K. R.; Kumaran, Kubaran; Kamil, S. Raja Mohamed; Srinivasan, T.

doi:10.1007/s11164-013-1325-7

Cited by 7 publications

(4 citation statements)

References 13 publications

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“…After completion of the reaction, petroleum ether was added to the reaction mixture with continuous stirring to obtain the final products in the form of precipitates. The precipitates were filtered, washed with distilled waterand purified by recrystallization.The advantages of these preparatory protocols are simplicity, very short reaction times, generality and the elaboration of substituted benzofuran–oxadiazole and benzofuran–triazole with high to excellent yields compared toconventional synthetic approaches and microwave methods already cited for generally synthetic approaches for oxadiazole and triazole derivatives, and specifically benzofuran–oxadiazole and benzofuran–triazole scaffolds [ 29 , 34 , 35 , 36 , 37 , 38 , 39 ].…”

Section: Methodsmentioning

confidence: 99%

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

et al. 2022

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Ultrasound- and microwave-assisted green synthetic strategies were applied to furnish benzofuran–oxadiazole 5a–g and benzofuran–triazole 7a–h derivatives in good to excellent yields (60–96%), in comparison with conventional methods (36–80% yield). These synthesized derivatives were screened for hemolysis, thrombolysis and anticancer therapeutic potential against an A549 lung cancer cell line using an MTT assay. Derivatives 7b (0.1%) and 5e (0.5%) showed the least toxicity against RBCs. Hybrid 7f showed excellent thrombolysis activity (61.4%) when compared against reference ABTS. The highest anticancer activity was displayed by the 5d structural hybridwith cell viability 27.49 ± 1.90 and IC50 6.3 ± 0.7 μM values, which were considerably lower than the reference drug crizotinib (IC50 8.54 ± 0.84 μM). Conformational analysis revealed the spatial arrangement of compound 5d, which demonstrated its significant potency in comparison with crizotinib; therefore, scaffold 5d would be a promising anticancer agent on the basis of cytotoxicity studies, as well as in silico modeling studies.

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Section: Methodsmentioning

confidence: 99%

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

et al. 2022

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“…After evaporating the solvent at 35-40°C, a white solid of ethyl carboxylate acyl hydrazones (158) and the part that did not dissolve in petroleum ether was recrystallized from ethanol; thus, 2,5-dialkyl 1,3,4oxadiazole (159) obtained. The corresponding compound 158 (10mmol) refluxed with hydrazine hydrate (25mmol) in propanol for 24h & then, cooled to RT to obtain the compound 160 80 .…”

Section: Synthesis Of 4-amino-35-dialkyl-124-triazolesmentioning

confidence: 99%

A Review on Methods of Synthesis of 1,2,4-Triazole Derivatives

Kaur¹,

Kaur²,

Goswami³

2018

Int Res J Pharm

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In the last few decades, heterocyclic compounds have been studied extensively owing to their interesting biological activities. One of them is triazole nucleus which exist in two isomeric forms: 1,2,3-triazole & 1,2,4-triazole. Out of which 1,2,4-triazole nucleus possess broad spectrum of pharmacological activities. This diversity in the pharmacological activity has attracted the attention of many researchers to explore the skeleton for its wide potential. This review summarizes the literature dealing with the conventional and green synthesis of 1,2,4-triazole nucleus.

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“…1) [6]. The aim of producing new powerful small molecules is to have novel therapeutic heterocyclic hybrid molecules in which two or more bioactive scaffolds are encapsulated inside a single molecule to perform multiple or combination biological activities [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Substituted 1,2,4-Triazole Containing Novel Small Molecules by Using Microwave

Gohil,

Noolvi

2023

JSMPM

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Green chemistry finds its most promising use in the synthesis of compounds using ecologically friendly, non-hazardous, non-irritant, gentle, and reproducible catalysts and solvents. The adoption of green chemistry approaches has recently been shown to significantly reduce chemical waste and reaction times in a number of organic synthesis processes. The objective of this research work is to develop an eco-friendly method for the Substituted 1,2,4-Triazole containing novel small molecules. The approach makes use of acid as starting material on reaction with hydrazine forms Acetyl-hydrazide. On condensation with nitrile and subsequent ring closure forms substituted 1,2,4-Triazole derivatives. This research work describes the synthesis of thirty-two unique 1,2,4-triazole containing novel small molecules. It has been shown that this technique is superior to other synthetic methods in terms of reaction time, yield, and energy efficiency along with use of green chemistry and microwave.

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Microwave-assisted synthesis of 1,2,4-triazole-3-carboxamides from esters and amines under neutral conditions

Cited by 7 publications

References 13 publications

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

A Review on Methods of Synthesis of 1,2,4-Triazole Derivatives

Synthesis of Substituted 1,2,4-Triazole Containing Novel Small Molecules by Using Microwave

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