Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety

Sayed, Samia M.; Khalil, Mohamed A.; Raslan, Mohamed A.

doi:10.5155/eurjchem.5.2.356-362.1022

Cited by 13 publications

(9 citation statements)

References 29 publications

(26 reference statements)

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“…In view of the previously mentioned findings and in continuation of our previous work aimed at the synthesis of a variety of heterocyclic ring systems for biological and pharmacological evaluation , we report here an efficient method for the synthesis of some pyrazole, 1,3,4‐thiadiazole, pyridine and 1,2,4‐triazolo[1,5‐a] pyrimidine derivatives attached to benzimidazole moieties.…”

Section: Introductionmentioning

confidence: 93%

Synthesis and Reactivity of Enaminones: Synthesis of Some 1,3,4‐Thiadiazole Linked to Pyrazole, Pyridine, Benzimidazolopyrimidine, Pyrazolopyrimidine, Pyrazolotriazine and Triazolotriazine Derivatives

Raslan

Omran

2015

Journal of Heterocyclic Chem

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1,3,4‐Thiadiazole‐enaminone (6) was synthesized via reaction of the benzamide (5) with DMF‐DMA. The simple thiadiazole‐enaminone (6) was used as a synthetic precursor for the synthesis of a wide variety of new heterocyclic compounds, including the 5‐substituted‐1,3,4‐thiadiazole derivatives (7), (8), (16), (17) and (18), which were obtained via reactions of (6) with nitrogen nucleophiles. Also, reactions of enaminone (6) with carbon nucleophiles afforded the respective 1,3,4‐thiadiazoles (10a,10b). Diazotization of the benzamide (20) with the heteroaromatic amine salts gave the hydrazone derivatives (21) and (22). Cyclization of the latter hydrazones yielded the corresponding pyrazolotriazine and 1,2,4‐triazolotriazine derivatives (23) and (24), respectively. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis.

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Section: Introductionmentioning

confidence: 93%

Synthesis and Reactivity of Enaminones: Synthesis of Some 1,3,4‐Thiadiazole Linked to Pyrazole, Pyridine, Benzimidazolopyrimidine, Pyrazolopyrimidine, Pyrazolotriazine and Triazolotriazine Derivatives

Raslan

Omran

2015

Journal of Heterocyclic Chem

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“…1,2,4-Triazole derivatives have physical-chemical and pharmacological properties that determine their widespread use, including as biologically active substances [1]. The objective reasons for this are the high synthetic potential of this heterocycle and the possibility of introducing various substitutes at the stage of ring formation [2,7]. In the literature there is a lot of data on a wide range of pharmacological activity of pyrazole derivatives (analgesic activity) and 1,2,4-triazole (antifungal, antipsychotic, antioxidant, anti-cancer activity) [1,[3][4][5][6][7][8][9].…”

Section: выводы получены с высокими выходами и чистотой N-r-2-(5-(5-mentioning

confidence: 99%

Synthesis, structure and properties of N-R-2-(5-(5-methyl-1H-pyrazole-3-yl)-4-phenyl-4H-1,2,4-triazole-3-ylthio)acetamides

Gotsulya

Fedotov

2019

Current Issues in Pharmacy and Medicine: Science and Practice

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Heterocyclic compounds remain the most promising group of compounds, through which the new drugs with characteristic list of properties are successfully created. Examples of this systems are 1,2,4-triazole and pyrazole. The presence in one molecule structure of fragments of two different azaheterocycles is synthetically interesting and allows increasing the probability to obtain biologically active substance with a wide spectrum of action. The aim of the work was to optimize the synthesis conditions and investigate the properties of N-R-2-(5-(5-methyl-1H-pyrazole-3-yl)-4phenyl-4H-1,2,4-triazole-3-ylthio)acetamides in case of change of chemical process conditions. Methods and results. Ethyl 5-methyl-1H-pyrazole-3-carboxylate, which was obtained by known techniques using acetone, diethyl oxalate, sodium methoxide, followed by hydrazine hydrate in equivalent amount, was used as the key starting reagent. The resulting ethyl 5-methyl-1H-pyrazole-3-carboxylate was used to carry out hydrazinolysis reactions and nucleophilic addition of phenyl isothiocyanate with subsequent alkaline heterocyclicization. The synthesized 5-(5-methyl-1H-pyrazol-3-yl)-4-phenyl-4H-1,2,4-triazole-3-thiole was used in alkylation reactions with promising reagents for the design of pharmacophoric fragments. The products of such reaction are N-R-2-(5-(5-methyl-1H-pyrazole-3-yl)-4-phenyl-4H-1,2,4-triazole-3-ylthio)acetamides. The structure of the resulting compounds was confirmed by elemental analysis, 1 H NMR spectroscopy, IR spectrophotometry. The individuality of the substances was determined by thin-layer chromatography and chromatographic mass spectrometry. For synthesized compounds, preliminary screening was performed using the PASS On-line ® software and molecular docking. Conclusions. N-R-2-5-(5-methyl-1H-pyrazole-3-yl)-4-phenyl-4H-1,2,4-triazole-3-ylthio)acetamides are obtained with high yields and purity, their properties are investigated. Синтез, будова та властивості N-R-2-(5-(5-метил-1H-піразол-3-іл)-4-феніл-4H-1,2,4-тріазол-3-ілтіо)ацетамідів А. С. Гоцуля, С. О. Федотов Гетероциклічні сполуки залишаються найбільш перспективною групою, за їхньою допомогою відбувається успішне створення нових лікарських засобів із характерним переліком властивостей. Прикладами таких систем є 1,2,4-тріазол і піразол. Наявність у структурі однієї молекули фрагментів двох різних азагетероциклів є синтетично цікавим і дає змогу збільшити ймовірність одержання біологічно активної субстанції з широким спектром дії. Мета роботи-оптимізація умов синтезу та дослідження властивостей N-R-2-(5-(5-метил-1H-піразол-3-іл)-4-феніл-4H-1,2,4-тріазол-3-ілтіо)ацетамідів при зміні умов перебігу хімічного процесу. Методи та результати. Як ключовий вихідний реагент використали етил 5-метил-1Н-піразол-3-карбоксилат, який одержали за відомими методиками з використанням ацетону, діетилоксалату, натрій метилату та з наступним використанням гідразин гідрату в еквівалентній кількості. Одержаний етил 5-метил-1Н-піразол-3-карбоксилат використали для реакцій гідразинолізу та нуклеофіл...

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“…In view of the aforementioned biological importance and in continuation of our interest in the synthesis of various heterocycles and its pharmacological properties , we report herein a facile synthetic strategy for synthesis of pyrazole, pyrazolo[1,5‐ a ][1,3,5]triazine, pyrazolo[1,5‐ a ]pyrimidines, imidazo[1,2‐ b ]pyrazole derivatives, and Schiff‐based derivatives linked to imidazo[2,1‐ b ]thiazole. The biological activities of the synthesized products will be reported in the extended work.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrazolo[1,5‐a][1,3,5]triazine, Pyrazolo[1,5‐a]pyrimidine, and Imidazo[1,2‐b]pyrazole Derivatives Based on Imidazo[2,1‐b]thiazole Moiety

Dawood

Sayed

Raslan

2017

Journal of Heterocyclic Chem

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3(5)‐Aminopyrazole derivative (6) has been synthesized by the reactions of the versatile unreported 2‐cyano‐N′‐(1‐(3‐methyl‐6‐phenylimidazo[2,1‐b]thiazol‐2‐yl)ethylidene)acetohydrazide (3) with phenyl isothiocyanate in KOH/DMF solution followed by reaction with methyl iodide and hydrazine hydrate. Reaction of compound 6 with some 1,3‐dicarbonyl compounds yielded pyrazolo[1,5‐a]pyrimidine derivatives (14–17). Alkylation of compound 6 with various halo reagents, followed by intramolecular cyclization, yielded the corresponding imidazo[1,2‐b]pyrazole derivatives 27, 29, 31, and 33. All newly synthesized compounds were elucidated by considering the data of both elemental analysis and spectral data.

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Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety

Cited by 13 publications

References 29 publications

Synthesis and Reactivity of Enaminones: Synthesis of Some 1,3,4‐Thiadiazole Linked to Pyrazole, Pyridine, Benzimidazolopyrimidine, Pyrazolopyrimidine, Pyrazolotriazine and Triazolotriazine Derivatives

Synthesis and Reactivity of Enaminones: Synthesis of Some 1,3,4‐Thiadiazole Linked to Pyrazole, Pyridine, Benzimidazolopyrimidine, Pyrazolopyrimidine, Pyrazolotriazine and Triazolotriazine Derivatives

Synthesis, structure and properties of N-R-2-(5-(5-methyl-1H-pyrazole-3-yl)-4-phenyl-4H-1,2,4-triazole-3-ylthio)acetamides

Synthesis of Pyrazolo[1,5‐a][1,3,5]triazine, Pyrazolo[1,5‐a]pyrimidine, and Imidazo[1,2‐b]pyrazole Derivatives Based on Imidazo[2,1‐b]thiazole Moiety

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