A simple and efficient synthesis of imidazoquinoxalines and spiroquinoxalinones via pictect-spengler reaction using Wang resin

Gorle, Simhachalam; L, Vaikunta Rao; Chiranjeevi, Y.; V, Dhanunjaya Rao A.; Mekala, Ramamohan; Tadiparthi, Krishnaji; Raghunadh, Akula

doi:10.1080/00397911.2021.2015783

Cited by 3 publications

(2 citation statements)

References 16 publications

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“…Therefore, developing new methodologies to prepare these heterocyclic molecules is an interesting goal in synthesis. Most of the approaches for the preparation of imidazoquinoxalines consist in the modified Pictet‐Spengler reaction between 2‐imidazolilarilamines and an aldehyde catalyzed by acids such as p ‐TsOH, [28] or Wang‐OSO 3 H resin [29] . In this field, Akula et al reported a one‐pot, two‐step synthesis of quinoxalines from nitrocompounds employing D ‐glucose as reductant and subsequent condensation of the amine catalyzed by acetic acid [30] .…”

Section: Resultsmentioning

confidence: 99%

“…Most of the approaches for the preparation of imidazoquinoxalines consist in the modified Pictet-Spengler reaction between 2-imidazolilarilamines and an aldehyde catalyzed by acids such as p-TsOH, [28] or Wang-OSO 3 H resin. [29] In this field, Akula et al reported a one-pot, two-step synthesis of quinoxalines from nitrocompounds employing Dglucose as reductant and subsequent condensation of the amine catalyzed by acetic acid. [30] In addition, Hulme et al have developed a multicomponent reaction for the synthesis of imidazo[1,5-a]quinoxalines from aryldiamines and 1,2ketoaldehydes.…”

Section: Synthesis Of Imidazo[15-a]quinoxalinesmentioning

confidence: 99%

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Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

Gómez‐Gil,

Cases,

Hernández‐Ruiz

et al. 2024

Eur J Org Chem

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We report the efficient, sustainable one‐pot synthesis of a wide variety of N‐polyheterocycles, such as imidazo‐quinolines and quinoxalines, and furoquinolines, from easily available nitroaromatics and glycols via a molybdenum catalytic domino reduction‐imine formation‐intramolecular cyclization‐oxidation sequence. It is worth highlighting that the recycling and incorporation of the waste carbonyl byproduct, generated in the reduction step, into the final compound is realized. In addition, the overall efficiency and atom economy of the process are further improved owing to the participation of one reaction intermediate as reductant that allows lowering the amount of external reducing agent employed.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Imidazo[15-a]quinoxalinesmentioning

confidence: 99%

Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

Gómez‐Gil,

Cases,

Hernández‐Ruiz

et al. 2024

Eur J Org Chem

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Design, Synthesis and Biological Evaluation of Imidazole-Substituted/Fused Aryl Derivatives Targeting Tubulin Polymerization as Anticancer Agents

Goel

Kharb

Rajput

2023

SynOpen

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The development of new pharmacologically active molecules targeting tubulin polymerization has recently attracted great interest in research groups. In efforts to develop new potent anticancer compounds, imidazole-tethered/fused pharmacologically active aryl derivatives possessing different substitution patterns targeting tubulin polymerization have been rationally designed and synthesized. The target molecules (P1-5 and KG1-5) were synthesized by multistep syntheses involving the reaction of intermediate 2-aminophenyl-tethered imidazoles with appropriate reactants in the presence of p-TsOH under different conditions. The synthesized compounds displayed moderate to good cytotoxicity, comparable to that of colchicine, against four cancer cell lines (MCF-7, MD-MBA-231, A549, and HCT-116). Compounds P2 and P5, with an imidazoloquinoxaline moiety, emerged as potential leads with cytotoxicity profiles against these cell lines similar to colchicine. Compounds P2 and P5 arrested cell division at the G2/M phase and prevented cancerous cell growth through induced apoptosis. These results favored the hypothesis that the compounds might act by binding to the colchicine binding site, which was further confirmed with the help of a tubulin polymerization inhibition assay. The results encourage the further exploration of imidazoloquinoxalines as promising leads that deserve advanced clinical investigation.

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Glucose as an eco-friendly reducing agent for a one-pot multicomponent synthesis of quinoxalines

Gorle

V.N.

et al. 2023

Synthetic Communications

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A simple and efficient synthesis of imidazoquinoxalines and spiroquinoxalinones via pictect-spengler reaction using Wang resin

Cited by 3 publications

References 16 publications

Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

Design, Synthesis and Biological Evaluation of Imidazole-Substituted/Fused Aryl Derivatives Targeting Tubulin Polymerization as Anticancer Agents

Glucose as an eco-friendly reducing agent for a one-pot multicomponent synthesis of quinoxalines

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