A bicyclo[3.1.1]heptano[4,3-c]pyrazole derived chiral auxiliary for dipolar cycloadditions

Molteni, Giorgio; Buttero, Paola Del

doi:10.1016/j.tetasy.2005.04.014

Cited by 23 publications

(10 citation statements)

References 12 publications

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“…[ 13 ] Additionally, they act as liquid crystals, [ 14 ] semiconductors, [ 15 ] and organic light‐emitting diodes. [ 16 ] Pyrazole and its analogs have also received considerable attention because of their synthetic application as chiral auxiliaries, [ 17 ] reagents in various multicomponent reactions, [ 18 ] and guanylating agents. [ 19 ] From the literature survey, it has also revealed that substituted pyrazoles are also utilized as chelating agents for the detoxification of undesired metal ions.…”

Section: Introductionmentioning

confidence: 99%

Exploration of pyrazole based aldo‐x bifunctional building blocks for the synthesis of pyrazole annulated molecular architectures

Sharma

Singh

2020

Journal of Heterocyclic Chem

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Over the last decade, the synthetic chemist's community has attracted attention towards aldo‐x precursors due to their versatility to afforded variety of heterocyclic frameworks. The aldo‐x bifunctional building blocks (AXB3s) contain two or more reactive sites with different reactivity, which may offer new opportunities for the introduction of diversity in core skeleton, which may be of great biological and medicinal relevance. In this context, pyrazole based AXB3s such as 4‐iodopyrazole‐3/5‐carbaldehyde may be explored for achieving pyrazole fused/linked heterocyclic skeletons by employing different organic transformations. Specifically, iodo substituted pyrazoles provide a new platform for the installation of desired pattern via transition‐metal catalyzed approaches. Herein, we have assembled the strategies towards the development of pyrazole substituted and fused molecular architectures by using 4‐iodopyrazole‐3/5‐carbaldehydes and pyrazole C‐3)/C5‐ carbaldehydes. The photophysical data of some fluorescent pyrazole derivatives have also been discussed.

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Section: Introductionmentioning

confidence: 99%

Exploration of pyrazole based aldo‐x bifunctional building blocks for the synthesis of pyrazole annulated molecular architectures

Sharma

Singh

2020

Journal of Heterocyclic Chem

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“…Some of the pyrazole derivatives have significant applications in material liquid crystals39 and electroluminescence40 properties. Besides, pyrazole rings not only used as synthetic reagents in multicomponent reactions41 and chiral auxiliaries,42 butit is also used as extraction reagents for many metal ions 43. In addition, some different companies successfully developed many pyrazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

<p>Grafting of multiwalled carbon nanotubes with pyrazole derivatives: characterization, antimicrobial activity and molecular docking study</p>

Metwally¹,

Saad²,

El-Wahab³

2019

IJN

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IntroductionIt is well known that the grafted multiwalled carbon nanotubes (MWCNTs) have antibacterial activity and lower cytotoxicity. Moreover, pyrazole derivatives have a broad spectrum of biological activity due to their fertile template for many medicinal drugs. On view of these findings we report herein the hybridization between MWCNTs and some pyrazole derivatives as antibacterial agents.Materials and methodsPyrazole and pyrazolone derivatives were grafted onto the surface of carboxylated MWCNTs via the reaction of carboxylated MWCNTs and the diazonium salts of pyrazoles and pyrazolones using mixed acid treatment. The insertion of the pyrazole and pyrazolone moieties was characterized by Fourier transform infrared (FTIR) spectroscopy, energy dispersion spectroscopy, transmission electron microscopy, X-ray diffraction and thermogravimetric (TGA).ResultsThe results indicate that pyrazole and pyrazolone moieties successfully attached on carboxylated MWCNTs surface. The neat pyrazole and pyrazolone derivatives and their corresponding carbon nanotubes were tested against Staphylococcus aureus, Bacillus subtilus, Escherichia coli, and Candida albicans bacteria, and Aspergillusniger fungi. The results showed that the grafted carbon nanotubes of pyrazole and pyrazolone derivatives have better antimicrobial activity than the neat pyrazole and pyrazolone derivatives. The molecular docking studies were performed on the most potent antimicrobial compounds to investigate the existence of the interactions between the most active inhibitors and Farnesyl pyrophosphate synthase (FPPS).ConclusionThe surface of the carboxylated MWCNTs was successfully grafted with some pyrazole derivatives. The antibacterial activity was investigated for the newly synthesized compounds and indicated that the grafted MWCNTs have good antibacterial activity toward some pathogenic types of bacteria.

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“…152-154°C; R f = 0.21 (hexane/EtOAc, 90 : 10, v/v); IR (neat): ν max (cm À 1 ) = 764 (CÀ S); 1 H NMR (500 MHz, CDCl 3 ): δ = 7.02-7.05 (m, 2 H, ArH), 7.24-7.25 (m, 1 H, ArH), 7.26-7.27 (m, 1 H, ArH), 7.37-7.43 (m, 7 H, ArH), 7.49-7.52 (m, 1 H, ArH), 7.93 (d, J = 7.9 Hz, 1 H, ArH), 8.10 (d, J = 8.1 Hz, 1 H, ArH) ppm; 13 C NMR (125 MHz, CDCl 3 ): δ = 106. 6,115.9 (d,J = 22.5 Hz),121.9,123.2,125.4,125.6,126.0,(d,J = 2.52 Hz),126.3,128.4,129.1 (d,J = 69.3 Hz),129.2,130.7 (d,J = 8.8 Hz),134.9,139.5,144.2,147.5,153.8,161.8,162.9 40.0, 105.9, 121.6, 123.7, 125.9, 126.7, 126.9, 129.0, 131.2, 133.8, 134.6, 137.0, 149.5, 153.9, 156.9 Ethyl 4-(benzo[d]thiazol-2-yl)-1-phenyl-1H-pyrazole-3-carboxylate (10D). Yield: 90% (0.172 g from 0.15 g) as a white solid; m.p.…”

Section: -(5-(4-fluorophenyl)-1-phenyl-1h-pyrazol-3-yl)benzo[d]thiazmentioning

confidence: 99%

“…[3] Relevance of this observation can be described due to their notable synthetic operations, favorable chemical characteristics and multiple reactive sites in pyrazole building blocks. [4] The pyrazole derivatives exhibit potential pharmacological properties [5] and application as chiral auxiliaries, [6] synthetic reagents in multicomponent reactions, [7] guanylating agents, [8] and chelating agents for several metal ions. [9] The pyrazole framework has also displayed enormous scope in smart materials and chemosensors due to its fluorescence properties.…”

Section: Introductionmentioning

confidence: 99%

Transition‐Metal‐Free C‐S Bond Forming Strategy towards Synthesis of Highly Diverse Pyrazole Tethered Benzothiazoles: Investigation of their Photophysical Properties

2020

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A metal-free domino approach has been devised towards construction of two CÀ S bonds for the synthesis of bioactive N, S-heterocycles. The developed method was extended for the preparation of structurally diverse pyrazole tethered benzothiazole frameworks by using one-pot operation of pyrazole C-3/4/5 carbaldehydes, electron rich aromatic amines and elemental sulfur. This protocol provides excellent fluorophores with several additional advantages such as transition metal-free approach, inexpensive and odorless sulfur source, superior atom economy, and broad substrate scope including gram scale synthesis. The synthesized pyrazole tethered benzothiazole fluorophores were evaluated for their luminescent properties including absorbance, excitation, emission, molar extinction coefficient, brightness, and Stokes shift. The photophysical studies revealed that these pyrazole and benzothiazole hybrids emerged as excellent fluorophores and could exhibit fluorescence quantum yield up to 66%.

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A bicyclo[3.1.1]heptano[4,3-c]pyrazole derived chiral auxiliary for dipolar cycloadditions

Cited by 23 publications

References 12 publications

Exploration of pyrazole based aldo‐x bifunctional building blocks for the synthesis of pyrazole annulated molecular architectures

Exploration of pyrazole based aldo‐x bifunctional building blocks for the synthesis of pyrazole annulated molecular architectures

<p>Grafting of multiwalled carbon nanotubes with pyrazole derivatives: characterization, antimicrobial activity and molecular docking study</p>

Transition‐Metal‐Free C‐S Bond Forming Strategy towards Synthesis of Highly Diverse Pyrazole Tethered Benzothiazoles: Investigation of their Photophysical Properties

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