Regioselective synthesis of pyrazole and pyridazine esters from chalcones and α-diazo-β-ketoesters

Nair, Deepa; Pavashe, Prashant; Katiyar, Savita; Namboothiri, Irishi N. N.

doi:10.1016/j.tetlet.2016.06.020

Cited by 30 publications

(15 citation statements)

References 54 publications

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“…The two-pot route is widely used for various synthesis of epoxy chalcone derivatives namely naphthofurans [73], 2-arylbenzo-furan [25], hydroxy ketone [74][75][76], hydrazinopyrimidine [77], pyridazine esters [24], azaisoflavones [78], bis-hydrazinecarboximidamide [79], difluoroboron ketoiminate […”

Section: Two-pot Routementioning

confidence: 99%

“…Pyrazine (20) is a reactive compound derived from the reaction of epoxy chalcones with diazo ester. Pyrazoline plays a vital role in drugs synthesis of minaprine (antidepressant) and pyridazomycin (anti-fungal) [24]. Other derivatives such as 1,2-isoxazole (21a) and pyrazoline (21b) have been prepared from the reaction of epoxy chalcone and hydroxylamine hydrochloride and hydrazine hydrate derivative, respectively.…”

Section: Anti-fungal and Anti-depressantmentioning

confidence: 99%

“…Epoxy chalcone and its derivatives are inimitable pharmacophore [15] for drug synthesis (e.g. diltiazem [16], rapamycin [17], epoxomicin [18], eponemycine [19], carmaphycin [20]) with virtuous anti-oxidant [21], anti-bacteria [22], anticancer [23], anti-depressant [24], anti-fungi [25] and antimicrobial [26] activities. Epoxy chalcone derivatives also offers numerous synthetic strategies of organic compounds via ring opening reaction under specific conditions to form C-C bond [27][28][29].…”

Section: Introductionmentioning

confidence: 99%

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One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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Epoxy chalcone is a heterocyclic molecule and an important precursor for the synthesis of biologically active compounds. This mini-review is elucidating the synthetic strategies of chalcone epoxide via one pot and two pot routes including nature of reactants, nature of catalyst and variety of catalyst to improve yield of desired product, biological applications and advantages and drawbacks of these synthetic strategies. One pot route has wide variety of reactants and efficient one is the condensation of aldehyde and ketone. However, two pot route is consisted of chalcone synthesis preceding to epoxy chalcone. The synthetic routes for the preparation of epoxy chalcone and the usage as a precursor for the synthesis of various organic molecules with biological application is comprehensively discussed. This review is outstanding in organic chemistry and pharmaceutical industries to produce new molecules with various applications. Graphic AbstractO O

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Section: Two-pot Routementioning

confidence: 99%

Section: Anti-fungal and Anti-depressantmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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“…In addition to BOR 2 and α ‐diazo‐ β ‐ketosulfone 48 , we employed α ‐diazo‐ β ‐ketoester 65 as a dipole with chalcone and synthesized the corresponding pyrazole derivatives 66 in moderate yields . An extensive optimization study was conducted to improve the yield of pyrazole ester formed by the 1,3‐dipolar cycloaddition of α ‐diazo‐ β ‐ketoester 65 and chalcone 64 using EtOH as the solvent of choice.…”

Section: Synthesis Of Pyrazoles From α‐Diazo‐β‐keto Substratesmentioning

confidence: 99%

Synthesis of Functionalized Pyrazoles via 1,3‐Dipolar Cycloaddition of α‐Diazo‐β‐ketophosphonates, Sufones and Esters with Electron‐Deficient Alkenes

Baiju

Namboothiri

2017

The Chemical Record

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1,3-Dipolar cycloaddition of diazo compounds with olefinic substrates is a promising atom-economic strategy for the construction of functionalized pyrazoles. Over the last few years, our group has been engaged in the synthesis of phosphonyl/sulfonylpyrazoles and pyrazole esters by employing Bestmann-Ohira Reagent (BOR) and its sulfur and ester analogs as 1,3-dipole precursors with various dipolarophiles. This account describes the novel synthetic methods developed in our laboratory, in the perspective of closely related work by others, for the synthesis of phosphonyl/sulfonylpyrazoles, pyrazole esters and the total synthesis of Withasomnine, a natural product, by using 1,3-dipolar cycloaddition as the key step.

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“…Indeed, during our literature survey, it is clearly noticeable that, pyridazine nucleus constructed by variant methods [18,20,[22][23][24][25], one of them involving reaction of β-aroyl acrylic acid and/or β-aroyl propionic acid with hydrazine monohydrate, which has been previously prepared in our lab [26,27].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Pharmacological Assay of Novel Compounds Based on Pyridazine Moiety as Potential Antitumor Agents

Ali

Ismail

El‐Azm

et al. 2019

Journal of Heterocyclic Chem

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In an endeavor to develop antitumor agents, we made a credible survey regarding synthesis, structure, and pharmacological assay of novel pyridazine derivatives, so that 2‐((6‐(4‐chloro‐3‐methylphenyl)pyridazin‐3‐yl)oxy)acetohydrazide 3 was utilized as scaffold to build novel compounds 4–19 by reaction with various electrophilic reagents, followed by determination and explanation atropisomerism phenomena and tauomerism ratio such as keto‐enol and lactam–lactim tautomers for some synthesized compounds. In vitro, these compounds were screened for antitumor efficacy versus two cell lines, namely, hepatocellular carcinoma and mammary gland breast cancer, by using MTT assay. Among the examined compounds, compound 16 was exhibited promising potent activity (IC50 = 8.67 ± 0.7 μM) versus HepG2 cell line. Meanwhile, compounds 3 and 16 were manifested the very highest efficacy (IC50 = 5.68 ± 0.6 and 9.41 ± 0.9 μM) versus MCF‐7 cell line.

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Regioselective synthesis of pyrazole and pyridazine esters from chalcones and α-diazo-β-ketoesters

Cited by 30 publications

References 54 publications

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Synthesis of Functionalized Pyrazoles via 1,3‐Dipolar Cycloaddition of α‐Diazo‐β‐ketophosphonates, Sufones and Esters with Electron‐Deficient Alkenes

Design, Synthesis, and Pharmacological Assay of Novel Compounds Based on Pyridazine Moiety as Potential Antitumor Agents

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