Synthesis and antimicrobial study of 1,4-dihydropyrano[2,3-c]pyrazole derivatives in the presence of amino-functionalized silica-coated cobalt oxide nanostructures as catalyst

Shahbazi, Shakiba; Ghasemzadeh, Mohammad Ali; Shakib, Pegah; Zolfaghari, Mohammad Reza; Bahmani, Mahmoud

doi:10.1016/j.poly.2019.04.063

Cited by 40 publications

(20 citation statements)

References 28 publications

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“…Finally, to demonstrate the potential of the present catalyst, for the preparative purpose, the reaction was also carried out with p ‐nitrobenzaldehyde on a gram scale, gave the excellent isolated yield 97 % (table , entry 2) which is comparable to those obtained for a small‐scale reaction. Though NGO efficiently catalyses the one‐pot synthesis of pyranopyrazole with a minimum catalyst load under a simple grinding condition in a shorter time, to understand the inherent catalytic potential of the NGO, control experiments were carried out with another similar type of catalysts such as graphite, GO, RGO (Reduced Graphene Oxide), GO‐APTES (aminopropyltriethoxysilane functionalized graphene oxide), liq. ammonia and con.…”

Section: Resultsmentioning

confidence: 99%

“…Pyrano[2,3‐ c ] pyrazoles are one of the privileged heterocyclic scaffolds know to exhibits different biological properties and also heterocyclic compounds bearing 4 H ‐pyran units have been playing a pivotal role in medicinal chemistry . Due to the continuous demand for pyranopyrazoles in medicinal chemistry, a variety of catalysts such as meglumine, nano‐Fe[phenyl salicylaldimine methyl pyranopyrazole]Cl 2 , isonicotinic acid, nano‐Fe 3 O 4 , glycine, montmorillonite K‐10, disulfonic acid imidazolium chloroaluminate, nanocrystalline zinc oxide, Y‐alumina, β‐cyclodextrin, per ‐6‐amino‐β‐cyclodextrin, bovine serum albumin and piperidine, has been used to synthesis of pyranopyrazoles . Though the synthesis of pyrano[2,3‐ c ] pyrazoles have studied in‐detail with different catalysts, owing to its paramount importance in pharmaceutical applications, the development of a greener and facile synthetic strategy still under investigation.…”

Section: Introductionmentioning

confidence: 99%

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Nitrogen‐Doped Graphene Oxide as a Sustainable Carbonaceous Catalyst for Greener Synthesis: Benign and Solvent‐free Synthesis of Pyranopyrazoles

Ganesan

Suresh

2020

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The development of benign strategies using the greener catalytic system is one of the prime tasks to improvise the greenness and sustainability in the synthesis of bioactive molecules. In the present work, a straightforward and sustainable methodology for the one-pot synthesis of dihydropyrano [2,3-c] pyrazole has been developed using nitrogen-doped graphene oxide (NGO) as a solid carbocatalyst under neat condition. The presence of high-density different types of nitrogen on the basal plane and the edges of the graphitic surface renders excellent active alkali sites and make it as a carbonaceous catalyst for the synthesis of a wide range of pyranopyrazoles with excellent yield. Present carbonaceous NGO catalysis the formation of pyranopyrazoles from diverse aldehydes and ketones under a solvent-free simple grinding condition that avoids chromatographic purifications. In this benign multicomponent synthesis, the NGO is highly stable and reusable without any loss in its catalytic activity even after eight successive reuses, which strongly enlighten the sustainable nature of the catalyst. Further analytical studies of the reused catalyst confirm the stability of the catalyst even after several reuses. The NGO catalyst paves a path for the development of sustainable nitrogen-based carbocatalyst for the benign multicomponent synthesis of bioactive molecules.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nitrogen‐Doped Graphene Oxide as a Sustainable Carbonaceous Catalyst for Greener Synthesis: Benign and Solvent‐free Synthesis of Pyranopyrazoles

Ganesan

Suresh

2020

ChemistrySelect

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“…Pyranopyrazoles 118 were efficiently synthesized in 88–95% yields via the one-pot four-component reactions of ethyl acetoacetate ( 6 ), hydrazine hydrate, aldehydes 34 , and malononitrile in the presence of Co 3 O 4 -SiO 2 -NH 2 nanocomposites as a catalyst ( Scheme 54 ) [ 90 ].…”

Section: Synthesis Of Pyrazolesmentioning

confidence: 99%

Substituted Pyrazoles and Their Heteroannulated Analogs—Recent Syntheses and Biological Activities

et al. 2021

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Pyrazoles are considered privileged scaffolds in medicinal chemistry. Previous reviews have discussed the importance of pyrazoles and their biological activities; however, few have dealt with the chemistry and the biology of heteroannulated derivatives. Therefore, we focused our attention on recent topics, up until 2020, for the synthesis of pyrazoles, their heteroannulated derivatives, and their applications as biologically active moieties. Moreover, we focused on traditional procedures used in the synthesis of pyrazoles.

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“…Shahbazi et al synthesized Co 3 O 4 @SiO 2 À NH 2 nanocomposites as a heterogeneous catalyst for an efficient one-pot multicomponent synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives via condensation of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile (Scheme 20). [43] The advantages of this protocol were high yields, short reaction times, ease of separation, recyclability of the magnetic nanocatalyst, and eco-friendly reaction conditions.…”

Section: Functionalized Metal Catalysts Immobilized On Silicamentioning

confidence: 99%

Recent Advances in Synthesis of Pyrazole Derivatives using Functionalized Catalysts Immobilized on Silica

et al. 2021

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The pyrazole moiety is found as an integral structural unit in a variety of pharmacologically and agrochemically significant chemicals. The anti-inflammatory (celecoxib), anti-obesity (rimonabant), analgesic (difenamizole), antipsychotic (CDPPB), H2-receptor agonist (betazole), and antidepressant (fezolamide) activities of pyrazole-based drugs have demonstrated their pharmacological importance. Various synthetic methodologies have been devised as a result of the above-mentioned advantages of pyrazole-based compounds, including solvent-free approach, catalyst-free method, homogeneous catalysis, heterogeneous catalysis, microwave irradiation technique, ultrasonication, etc. In the area of heterogeneous catalysis, silica functionalized catalysts have garnered a lot of interest among diverse heterogeneous catalysts. The significant advancements in silica functionalized heterogeneous catalysts for the production of pyrazole-based compounds are highlighted in this review.

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Synthesis and antimicrobial study of 1,4-dihydropyrano[2,3-c]pyrazole derivatives in the presence of amino-functionalized silica-coated cobalt oxide nanostructures as catalyst

Cited by 40 publications

References 28 publications

Nitrogen‐Doped Graphene Oxide as a Sustainable Carbonaceous Catalyst for Greener Synthesis: Benign and Solvent‐free Synthesis of Pyranopyrazoles

Nitrogen‐Doped Graphene Oxide as a Sustainable Carbonaceous Catalyst for Greener Synthesis: Benign and Solvent‐free Synthesis of Pyranopyrazoles

Substituted Pyrazoles and Their Heteroannulated Analogs—Recent Syntheses and Biological Activities

Recent Advances in Synthesis of Pyrazole Derivatives using Functionalized Catalysts Immobilized on Silica

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