Phenacyl Bromides Revisited: Facile Synthesis of Some New Pyrazoles, Pyridazines, and Their Fused Derivatives

Abdelrazek, Fathy M.; Hassaneen, Hamdi M.; Nassar, Ekhlass; Jager, Anna

doi:10.1002/jhet.1664

Cited by 6 publications

(3 citation statements)

References 12 publications

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“…Because of the enormous request on these compounds, some new functional compounds bearing two or more of the aforementioned units were required for biological activity studies. 1,4‐Diacetyl benzene 1 seemed a suitable candidate to fulfill this objective via a sequence of reactions similar to that recently reported .…”

Section: Introductionmentioning

confidence: 53%

A Novel Synthesis of Some 1,4‐Phenylene‐bis‐heterocyclic Derivatives and of Some Pyran, Pyrano[2,3‐c]pyrazole, and Pyrano[2,3‐d]pyrimidine Derivatives [1]

Abdelrazek

Helal

Hebishy

et al. 2014

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).p-Diacetyl benzene 1 undergoes bromination to afford p-bromoacetyl phenacyl bromide 2. Compound 2 reacts with twofold excess of malononitrile to afford 2-{2-[4-(3,3-Dicyanopropionyl)-phenyl]-2-oxo-ethyl}malononitrile 3. Compound 3 could be cyclized to afford the 1,4-phenylene-bis-furan derivative 4. Compound 3 reacts also with a twofold excess of hydrazine hydrate and phenyl hydrazine under dry conditions at RT to afford the bis-pyrazole derivatives 5a,b, respectively. The reaction of 5a,b with the same reagents in refluxing dioxane afforded the bis-pyrazolopyridazine derivatives 7a,b, respectively. The azo coupling of compound 3 with arene diazonium salts afforded the bis-pyrazole derivatives 9a-c. The β-keto esters 10a,b react with benzaldehyde and malononitrile in a one pot synthesis to afford the pyran derivatives 11a,b. These latter compounds react with hydrazine hydrate and urea derivatives to afford the pyrano[2,3-c]pyrazoles 15a,b and the pyrano[2,3-d]pyrimidine derivatives 17a,b, respectively.

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Section: Introductionmentioning

confidence: 53%

A Novel Synthesis of Some 1,4‐Phenylene‐bis‐heterocyclic Derivatives and of Some Pyran, Pyrano[2,3‐c]pyrazole, and Pyrano[2,3‐d]pyrimidine Derivatives [1]

Abdelrazek

Helal

Hebishy

et al. 2014

Journal of Heterocyclic Chem

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“…All compounds were within ± 0.4% of the theoretical values. Compounds 13, 15a 66 and 17a-f 67 , 68 were prepared according to previously reported procedures.…”

Section: Methodsmentioning

confidence: 99%

New 1,2,3-triazole/1,2,4-triazole hybrids linked to oxime moiety as nitric oxide donor selective COX-2, aromatase, B-RAF ^V600E and EGFR inhibitors celecoxib analogs: design, synthesis, anti-inflammatory/anti-proliferative activities, apoptosis and molecular modeling study

Fadaly,

Nemr,

Zidan

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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A new series of bis-triazole 19a-l was synthesised for the purpose of being hybrid molecules with both anti-inflammatory and anti-cancer activities and assessed for cell cycle arrest, NO release. Compounds 19c , 19f , 19h , 19 l exhibited COX-2 selectivity indexes in the range of 18.48 to 49.38 compared to celecoxib S.I. = 21.10), inhibit MCF-7 with IC 50 = 9–16 μM compared to tamoxifen (IC 50 = 27.9 μM). and showed good inhibitory activity against HEP-3B with IC 50 = 4.5–14 μM compared to sorafenib (IC 50 = 3.5 μM) (HEP-3B). Moreover, derivatives 19e , 19j , 19k , 19 l inhibit HCT-116 with IC 50 = 5.3–13.7 μM compared to 5-FU with IC 50 = 4.8 μM (HCT-116). Compounds 19c , 19f , 19h , 19 l showed excellent inhibitory activity against A549 with IC 50 = 3–4.5 μM compared to 5-FU with IC 50 = 6 μM (A549). Compounds 19c, 19f, 19h, 19 l inhibit aromatase (IC 50 of 22.40, 23.20, 22.70, 30.30 μM), EGFR (IC 50 of 0.112, 0.205, 0.169 and 0.066 μM) and B-RAF V600E (IC 50 of 0.09, 0.06, 0.07 and 0.05 μM).

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“…[6,[8][9][10] In related studies, mono-substituted malononitriles 1b-f were shown to be useful for the efficient synthesis of diaminopyrazoles 2b-f. [11][12][13][14] However, the formation of 2g via reaction of phenacyl malononitrile (1g) with hydrazine hydrate could not be repeated in our hands. [15][16][17] Treatment of 1g with hydrazine hydrate in ethanolic solution as described by Abdelrazek et al [15][16][17] or in absence of solvent in dry condition as suggested recently [18] has only result in the formation of 6 in 97% yield. What is more, the use of dry conditions was claimed even though hydrazine hydrate already contains one molecule of water.…”

Section: Introductionmentioning

confidence: 99%

Simple Efficient Routes for the Preparation of Pyrazoleamines and Pyrazolopyrimidines: Regioselectivity of Pyrazoleamines Reactions with Bidentate Reagents

Moustafa¹,

Al‐Mousawi²,

Elnagdi³

2016

Croat. Chem. Acta

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Simple and efficient routes for the preparation of 2-amino-5-phenyl-4,5-dihydrofuran-3-carbonitrile (12), 2-oxo-5-phenyl-tetrahydrofuran-3-carbonitrile (13) and the 3,5-diaminopyrazole derivative 2h were developed. The results of the reactivity profiles of 12 and 2h are reported and the previously investigated reaction of pyrazole-3,5-diamine (2b) with acrylonitrile to yield compound (31), a N-1 acylation product, is currently justified by using X-ray crystallographic analysis. Taken together, the observation of alkenes and alkynes substitution when reacting with 3,5-diaminopyrazole derivative 2h is explained by the terminal electron withdrawing group. This pattern of substitution is attributed to involvement of sterically unhindered electrophiles primarily at the N-1 position.

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Phenacyl Bromides Revisited: Facile Synthesis of Some New Pyrazoles, Pyridazines, and Their Fused Derivatives

Cited by 6 publications

References 12 publications

A Novel Synthesis of Some 1,4‐Phenylene‐bis‐heterocyclic Derivatives and of Some Pyran, Pyrano[2,3‐c]pyrazole, and Pyrano[2,3‐d]pyrimidine Derivatives [1]

A Novel Synthesis of Some 1,4‐Phenylene‐bis‐heterocyclic Derivatives and of Some Pyran, Pyrano[2,3‐c]pyrazole, and Pyrano[2,3‐d]pyrimidine Derivatives [1]

New 1,2,3-triazole/1,2,4-triazole hybrids linked to oxime moiety as nitric oxide donor selective COX-2, aromatase, B-RAF ^V600E and EGFR inhibitors celecoxib analogs: design, synthesis, anti-inflammatory/anti-proliferative activities, apoptosis and molecular modeling study

Simple Efficient Routes for the Preparation of Pyrazoleamines and Pyrazolopyrimidines: Regioselectivity of Pyrazoleamines Reactions with Bidentate Reagents

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Phenacyl Bromides Revisited: Facile Synthesis of Some New Pyrazoles, Pyridazines, and Their Fused Derivatives

Cited by 6 publications

References 12 publications

A Novel Synthesis of Some 1,4‐Phenylene‐bis‐heterocyclic Derivatives and of Some Pyran, Pyrano[2,3‐c]pyrazole, and Pyrano[2,3‐d]pyrimidine Derivatives [1]

A Novel Synthesis of Some 1,4‐Phenylene‐bis‐heterocyclic Derivatives and of Some Pyran, Pyrano[2,3‐c]pyrazole, and Pyrano[2,3‐d]pyrimidine Derivatives [1]

New 1,2,3-triazole/1,2,4-triazole hybrids linked to oxime moiety as nitric oxide donor selective COX-2, aromatase, B-RAF V600E and EGFR inhibitors celecoxib analogs: design, synthesis, anti-inflammatory/anti-proliferative activities, apoptosis and molecular modeling study

Simple Efficient Routes for the Preparation of Pyrazoleamines and Pyrazolopyrimidines: Regioselectivity of Pyrazoleamines Reactions with Bidentate Reagents

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New 1,2,3-triazole/1,2,4-triazole hybrids linked to oxime moiety as nitric oxide donor selective COX-2, aromatase, B-RAF ^V600E and EGFR inhibitors celecoxib analogs: design, synthesis, anti-inflammatory/anti-proliferative activities, apoptosis and molecular modeling study