Straightforward copper-catalyzed synthesis of pyrrolopyrazoles from halogenated pyrazolecarbaldehydes

Nayak, Maloy; Batchu, Harikrishna; Batra, Sanjay

doi:10.1016/j.tetlet.2012.05.148

Cited by 27 publications

(8 citation statements)

References 29 publications

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“…A Cu‐catalyzed C‐N cross‐coupling reaction between 4‐iodo‐pyrazole‐3‐carbaldehyde 17 and ethyl isocyanoacetate ( 105 ) furnished the pyrrolopyrazoles 106 as presented in Scheme 24. [ 41 ] Gratifyingly, all pyrazole carbaldehydes 17 gave the products 106 in good to excellent yields (68‐80%).…”

Section: Copper‐catalyzed Approaches For the Synthesis Of Pyrazole Fumentioning

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: Copper‐catalyzed Approaches For the Synthesis Of Pyrazole Fumentioning

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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“…The organic layer was separated, while the aqueous layer was further extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and concentrated over reduced pressure to afford a pure product as a white solid ( Figure 4 ) [ 53 , 54 ]. Edaravone ( Figure 5 ) has been used to treat acute-phase cerebral infarction for almost 20 years in Japan.…”

Section: Therapeutic Strategies For Als Targetsmentioning

confidence: 99%

Comprehensive Research on Past and Future Therapeutic Strategies Devoted to Treatment of Amyotrophic Lateral Sclerosis

Sever

Çi̇ftçi̇

DeMi̇rci̇

et al. 2022

IJMS

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Amyotrophic lateral sclerosis (ALS) is a rapidly debilitating fatal neurodegenerative disorder, causing muscle atrophy and weakness, which leads to paralysis and eventual death. ALS has a multifaceted nature affected by many pathological mechanisms, including oxidative stress (also via protein aggregation), mitochondrial dysfunction, glutamate-induced excitotoxicity, apoptosis, neuroinflammation, axonal degeneration, skeletal muscle deterioration and viruses. This complexity is a major obstacle in defeating ALS. At present, riluzole and edaravone are the only drugs that have passed clinical trials for the treatment of ALS, notwithstanding that they showed modest benefits in a limited population of ALS. A dextromethorphan hydrobromide and quinidine sulfate combination was also approved to treat pseudobulbar affect (PBA) in the course of ALS. Globally, there is a struggle to prevent or alleviate the symptoms of this neurodegenerative disease, including implementation of antisense oligonucleotides (ASOs), induced pluripotent stem cells (iPSCs), CRISPR-9/Cas technique, non-invasive brain stimulation (NIBS) or ALS-on-a-chip technology. Additionally, researchers have synthesized and screened new compounds to be effective in ALS beyond the drug repurposing strategy. Despite all these efforts, ALS treatment is largely limited to palliative care, and there is a strong need for new therapeutics to be developed. This review focuses on and discusses which therapeutic strategies have been followed so far and what can be done in the future for the treatment of ALS.

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“…One should notice that the authors used both tautomeric halogeno pyrazolecarbaldehyde 82 and 85 to get the corresponding pyrrolopyrazoles 84 and 86. 54 A plausible mechanism for the formation of pyrrolopyrazole involving a condensation reaction of Cu-mediated C-N cross coupling and deformylation sequence was proposed by the authors (Scheme 23). In addition, even less substituted pyrazoles could react under such conditions and gave pyrrole-fused heterocycle in similar yields.…”

Section: Scheme 22 Synthesis Of Indole-fused Pyrazole With Potent Revmentioning

confidence: 99%

‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space

Passador

Thorimbert

Botuha³

2018

Synthesis

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William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.1 Introduction2 Heteroaromatic Rings of the Future: The Synthetic challenge?2.1 4-Pyrido[1,3]oxazin-4-one-P1 2.2 Pyrrolo[2,1-b][1,3]oxazin-4-one-P4 2.3 Furo[2,1-e]pyridazin-4(1H)-one-P5 2.4 Isoxazolo[3,4-c]pyridin-7-one-P6 2.5 5H,6H-[1,2]Thiazolo[5,4-c]pyridin-5-one-P7 2.6 4H,5H-Furo[3,2-b]pyridin-5-one-P8 2.7 1H,5H,6H-Pyrazolo[3,4-c]pyridin-5-one-P9 2.8 Thieno[3,4-c]pyridazine-P10 2.9 Pyrrolo[1,2-c][1,2,3]triazine-P11 2.10 Thieno[3,4-a]oxazole-P12 2.11 2,4-Dihydropyrrolo[3,2-c]pyrazole-P13 2.12 Pyrazolo[1,5-b]isoxazole-P14 2.13 Imidazo[1,5-c]pyrimidin-3(2H)-one-P16 2.14 Cyclopenta[b][1,4]oxazin-5(4H)-one-P17 2.15 2,3-Dihydro-2,6-naphthyridin-3-one-P18 3 Conclusion

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Straightforward copper-catalyzed synthesis of pyrrolopyrazoles from halogenated pyrazolecarbaldehydes

Cited by 27 publications

References 29 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

Comprehensive Research on Past and Future Therapeutic Strategies Devoted to Treatment of Amyotrophic Lateral Sclerosis

‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space

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