Three-Component Synthesis of Spiro[Indoline-3,4'-Pyrano[3,2-b]Pyran]- 2,8'-Diones Using a One-Pot Reaction

Rahmati, Abbas; Khalesi, Zahra; Kenarkoohi, Tahmineh

doi:10.2174/13862073113166660067

Cited by 8 publications

(3 citation statements)

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“…Thus, the research for the development of a synthetic methodology for the synthesis of these bioactive motifs is in great demand. These series of kojic acid derivatives have been synthesized with threecomponent reaction of a primary or secondary amine, aldehydes and kojic acid by Mannich-type condensation reaction in the presence of a different catalysts such as DABCO [26], nano-SiO 2 -sulfuric acid [27], Ce 2 (SO 4 ) 3 •5H 2 O [28], InCl 3 [29], NiFe 2 O 4 @MOF-5 [30] and βCD [31].…”

Section: Introductionmentioning

confidence: 99%

Hyper-cross-linked β-cyclodextrin nanosponge: a three-dimensional, porous and biodegradable catalyst in the one-pot synthesis of kojic acid-based heterocyclic compounds

2020

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In the present study, β-cyclodextrin-based nanosponges were prepared by reaction of β-cyclodextrin with dicarbonyl imidazole as a crosslinker agent. The synthesized polycarbonate nanosponge was characterized by FT-IR spectroscopy, thermogravimetric analysis, scanning electron microscopy and Brunauer-Emmett-Teller. The catalytic activity of β-cyclodextrin-based nanosponges was successfully tested in the one-pot three-component condensation of kojic acid, aromatic aldehydes and various aromatic amines. The superiority of this new strategy is short reaction times, high yields and utilizing of biodegradable and nontoxic nanocatalyst.

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Section: Introductionmentioning

confidence: 99%

Hyper-cross-linked β-cyclodextrin nanosponge: a three-dimensional, porous and biodegradable catalyst in the one-pot synthesis of kojic acid-based heterocyclic compounds

2020

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“…Earlier 3a , d were obtained in reactions catalyzed by N ‐doped graphene quantum dots modified with CuO (0D)/ZnO (1D) heterojunctions nanocatalyst, [ 52 ] or Cu(OTf) 2 [ 53 ] or DABCO [ 54 ] in 85–95% yields.…”

Section: Resultsmentioning

confidence: 99%

Electrochemically induced assembling of isatins, kojic acid, and malonic acid derivatives into substituted spiro[indole‐3,4′‐pyran]‐2(1H)‐one scaffold and predicting potential protein targets

Elinson

Ryzhkova

Vereshchagin

et al. 2022

Journal of Heterocyclic Chem

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Electrochemically induced multicomponent assembling of isatins, kojic acid, and malonic acid derivatives in n-propanol in the presence of sodium iodide as an electrolyte in an undivided cell results in the formation of unsymmetrical spiro(indole-3,4 0 -pyrano[3,2-b]pyranes) in 86-98% yields. The optimized reaction conditions and a mechanistic rationale for this catalytic electrochemical transformation are presented. This new electrocatalytic multicomponent process is a facile and efficient environmentally benign way to the functionalized unsymmetrical spiro(indole-3,4 0 -pyrano[3,2-b]pyranes), containing inserted kojic acid fragment, which are perspective compounds for different biomedical applications, among them anticonvulsant, anti-cancer, anti-AIDS agents, and anti-inflammatory remedies. All synthesized compounds were investigated using a molecular docking procedure. The results of prediction were incorporated in one pool of potential targets. The automated method was proposed and performed for the docking procedure. It is distinct from screening by higher accuracy, and it is much more scalable than the classic docking procedure. It was found that the synthesized compounds are potential ligands for 4OHK (glucokinase regulatory protein) and 3V2B (human poly [adp-ribose] polymerase 15) proteins.

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“…Thus, there has been a rising significance of developing a general and diverse method for the synthesis of pyrano[4,3‐ b ]pyran derivatives. A number of synthetic approaches have been introduced in recent years . As per the literature survey, few methods were reported for the synthesis of pyrano[4,3‐ b ]pyran derivatives using a variety of reagents have been employed to accomplish this transformation.…”

Section: Introductionmentioning

confidence: 99%

Protic Ionic Liquid Promoted One Pot Synthesis of 2‐amino‐4‐(phenyl)‐7‐methyl‐5‐oxo‐4H,5H‐pyrano[4,3‐b]pyran‐3‐carbonitrile Derivatives in Water and Their Antimycobacterial Activity

Mohire

Chandam

Patil

et al. 2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).One pot three component reaction of 4-hydroxy-6-methylpyran-2-one, 3-methoxy benzaldehyde, and malononitrile in water using protic ionic liquid as a catalyst at room temperature afforded pyrano[4,3-b]pyran derivatives. Protic ionic liquid has been proved to be an efficient and mild catalyst for the synthesis of pyrano[4,3-b]pyran scaffolds due to their highly polar nature. The notable aspects of protic ionic liquid are easy availability, improved reaction rates, high product yields, simple workup procedure, recyclability, and reusability. Molecules docking studies have been performed on enzyme enoyl-ACP-reductase from Mycobacterium tuberculosis. The molecular docking simulation indicated plausible π-alkyl and alkyl-alkyl interactions between the amino acids and scaffolds. The synthesized derivatives have been evaluated for their in vitro antituberculotic activity against M. tuberculosis H 37 RV strain using Microplate Alamar Blue Assay method. Together, biological activity data and docking data showed that the tested scaffolds exhibited excellent antituberculotic activity.

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Three-Component Synthesis of Spiro[Indoline-3,4'-Pyrano[3,2-b]Pyran]- 2,8'-Diones Using a One-Pot Reaction

Cited by 8 publications

References 0 publications

Hyper-cross-linked β-cyclodextrin nanosponge: a three-dimensional, porous and biodegradable catalyst in the one-pot synthesis of kojic acid-based heterocyclic compounds

Hyper-cross-linked β-cyclodextrin nanosponge: a three-dimensional, porous and biodegradable catalyst in the one-pot synthesis of kojic acid-based heterocyclic compounds

Electrochemically induced assembling of isatins, kojic acid, and malonic acid derivatives into substituted spiro[indole‐3,4′‐pyran]‐2(1H)‐one scaffold and predicting potential protein targets

Protic Ionic Liquid Promoted One Pot Synthesis of 2‐amino‐4‐(phenyl)‐7‐methyl‐5‐oxo‐4H,5H‐pyrano[4,3‐b]pyran‐3‐carbonitrile Derivatives in Water and Their Antimycobacterial Activity

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