A simple procedure for the synthesis of novel 3-(benzofur-2-yl)pyrazole-based heterocycles

Baashen, Mohammed; Abdel‐Wahab, Bakr F.; El‐Hiti, Gamal A.

doi:10.1007/s11696-017-0209-5

Cited by 9 publications

(9 citation statements)

References 39 publications

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“…[24] In the current work, a novel series of azines was produced by simple and efficient synthetic procedures from phosphonic dihydrazide, as part of our research program on the synthesis of novel heterocycles. [25][26][27][28][29] KEYWORDS Phosphonic dihydrazide; azines; nucleophilic substitution reaction; heterocycles; bis(N'arylpropanehydrazonoyl produced in low yields along with 1. Such results are not in agreement with the reported ones.…”

Section: Resultsmentioning

confidence: 99%

Facile, mild and efficient synthesis of azines using phosphonic dihydrazide

Khidre

Mohamed

Kariuki

et al. 2019

Phosphorus, Sulfur, and Silicon and the Related Elements

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Several bis(N'-arylpropanehydrazonoyl chlorides) were synthesized in good yields from condensation reactions of hydrazonoyl chlorides and phosphonic dihydrazide. Under the conditions employed, none of the expected phosphorylhydrazines were isolated. Nucleophilic substitution of bis(N'arylpropanehydrazonoyl chlorides) with thiophenol, sodium phenylsulfinate, hydroxyl amine, and piperidine afforded the corresponding azines. Similarly, 1,2-bis(heteroaryl)ethylidene)hydra-zines were produced from reaction of phosphonic dihydrazide and heteroaryl methyl ketones. The structures of the products were confirmed by NMR and IR spectral data along with X-ray crystal structure determination and their purities were confirmed by the elemental analyses.

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Section: Resultsmentioning

confidence: 99%

Facile, mild and efficient synthesis of azines using phosphonic dihydrazide

Khidre

Mohamed

Kariuki

et al. 2019

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…[29][30][31][32][33][34] Recently, we have reported several procedures for the synthesis of various heterocycles. [35][36][37][38][39][40] Herein, we report efficient and simple methods for the synthesis of heterocycles containing the 1,2,3-triazole moieties. These heterocycles, synthesized from 1,2,3-triazole-4-carbohydrazides, have important applications in many fields.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel heterocycles using 1,2,3‐triazole‐4‐carbohydrazides as precursors

Mohamed

Khidre

Kariuki

et al. 2019

Journal of Heterocyclic Chem

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Herein, we report the synthesis of various heterocyclic ring systems containing 1,2,3‐triazole from the reactions of acid hydrazides and commercially available reagents, using efficient and simple procedures. Reactions of certain 1,2,3‐triazole‐4‐carbohydrazides and α‐bromoketones in boiling ethanol afforded the corresponding hydrazones rather than the expected triazines. The hydrazones could also be synthesized in 85‐90% yield via an alternative pathway that involved the reaction of 1,2,3‐triazole‐4‐carbohydrazides and 4‐acetyl‐1,2,3‐triazoles in boiling ethanol containing glacial acetic acid. Reaction of one of the 4‐carbohydrazides with carbon disulfide, followed by the reaction with hydrazine hydrate, gave 4H‐1,2,4‐triazole‐3‐thiol in 73% yield, which further reacted with other α‐bromoketones in boiling ethanol to afford 7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines in 82‐84% yields. Additionally, reactions of certain carbohydrazides with ethyl 2‐cyano‐3,3‐bis(methylthio)acrylate gave 1‐aryl‐1H‐1,2,3‐triazole‐4‐carbohydrazides rather than the expected 1H‐pyrazole‐4‐carboxylates.

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“…They have a range of medicinal and pharmaceutical importance and can be used as antibacterial, antifungal, and anticancer agents . Therefore, we became interested in the synthesis of heterocycles using both benzofuran and thiocarbohydrazides as precursors as a contribution of our research in the area heterocycles chemistry . The synthetic processes reported in this work are simple and does not require the use of expensive or hazardous catalysts.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Efficient Process for the Synthesis of Novel Heterocycles Containing Benzofuran Moiety Using Thiocarbohydrazide as a Precursor

Baashen

2019

Journal of Heterocyclic Chem

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A simple and efficient process for the synthesis of novel heterocycles starting from thiocarbohydrazide was reported. Reaction of 2‐acetylbenzofuran (1) and thiocarbohydrazide (2) in ethanol containing acetic acid produced the corresponding thiocarbohydrazone 3 in 86% yield. Reaction of 3 and isatin (4) gave N,2‐bis(2‐oxoindolin‐3‐ylidene)hydrazine‐1‐carbothiohydrazine (6) in 65% yield, rather than the expected product, 3‐[(1‐methyl‐1‐benzofur‐2‐ylmethylidene)amino]‐1‐{[(3Z)‐2‐oxo‐2,3‐dihydro‐1H‐indol‐3‐ylidene]amino}thiourea (5). Reaction of 2‐((3‐(benzofuran‐2‐yl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)methylene)hydrazine carbothioamide (9) and chloroacetic acid or hydrazonoyl chloride 11 in basic medium gave (Z)‐2‐((E)‐((3‐(benzofuran‐2‐yl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)methylene)hydrazono)thiazolidin‐4‐one (10) or 2‐((E)‐2‐((3‐(benzofuran‐2‐yl)‐1‐ phenyl‐1H‐pyrazol‐4‐yl)methylene)hydrazinyl)‐4‐((E)‐(4‐fluorophenyl)diazenyl)‐5‐methylthiazole (12) in 62% or 74%, respectively.

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A simple procedure for the synthesis of novel 3-(benzofur-2-yl)pyrazole-based heterocycles

Cited by 9 publications

References 39 publications

Facile, mild and efficient synthesis of azines using phosphonic dihydrazide

Facile, mild and efficient synthesis of azines using phosphonic dihydrazide

Synthesis of novel heterocycles using 1,2,3‐triazole‐4‐carbohydrazides as precursors

A Simple and Efficient Process for the Synthesis of Novel Heterocycles Containing Benzofuran Moiety Using Thiocarbohydrazide as a Precursor

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