An Efficient One‐Pot Four‐Component Synthesis of Some New Spirooxindole Dihydropyridine Using Alum as a Heterogeneous Green Catalyst

Mohammadi, Ali A.; Taheri, Salman; Amouzegar, Ali

doi:10.1002/jhet.2757

Cited by 14 publications

(3 citation statements)

References 51 publications

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“…The researchers decided to use this heterogeneous catalyst in the one‐pot 4‐MCR between isatin derivatives, 1,1‐bis(methylthio)‐2‐nitroethylene, diamines and 1,3‐indandione, affording the 4‐nitro‐2,3‐dihydrospiroimidazo[1,2‐ a ]indeno[2,1‐ e ]pyridine‐5,3′‐indoline‐2′,6(1 H )‐dione derivatives in good to excellent yields (10 examples). The reaction showed good scope, short reaction times, mild conditions and easy work‐up [183] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

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Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Section: Spirooxindole Derivativesmentioning

confidence: 99%

“…trisodium citrate dehydrate [60] Borax [68] SDS [108] sodium p ‐toluene sulfonate [132] TBAB [133] KAl(SO 4 ) 2 .12H 2 O [183] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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“…In 2016, Mohammadi and co-workers have synthesized 1 H -imidazol[1,2- a ]indeno[2,1- e ]pyridine-6(5 H )-one derivatives via a one-pot four-component condensation of aldehydes, 1,3-indandione, diamine, and nitro ketene dithioacetal using KAl(SO 4 ) 2 .12H 2 O (alum) in good to excellent yields 31 . In 2017, Mohammadi et al have described a one-pot four-component, and efficient method by reaction of isatins, 1,3-indandione, diamine, and nitro ketene dithioacetal in the presence of Alum as a green catalyst for the synthesis of 4-nitro-2,3-dihydrospiro[imidazo[1,2- a ]indeno[2,1- e ]pyridine-5,3 ' -indoline]-2 ' ,6(1 H )-dione derivatives in good yields 32 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of diverse spiro-imidazo pyridine-indene derivatives via acid-promoted annulation reaction of bindone and heterocyclic ketene aminals

Nasri

Bayat

Miankooshki

2022

Sci Rep

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A new multi-component reaction for the synthesis of novel and diverse spiro-imidazo pyridine-indene derivatives named spiro[imidazo[1,2-a]indeno[2,1-e]pyridine-5,1′-indene and indenylidene-1H-spiro[imidazo[1,2-a]pyridine-7,1′-indene was successfully developed by the reaction between heterocyclic ketene aminals (generated from 1,1-bis(methylthio)-2-nitro ethylene and diamine) and [1,2′-biindenylidene]-1′,3,3′-trione (bindone) (in situ generated from self-condensation of 1,3-indandion) by using malononitrile as a promoter or as one of the precursors respectively in the presence of p-TSA as the acid catalyst in EtOH as reaction medium under reflux conditions. Depending on whether the reaction is single-step or two-step, malononitrile can act as a promoter or reactant. The convenient one-pot operation, straightforward isolation without using additional purification methods, and the use of a variety of diamines and cysteamine hydrochloride causing a variety of structural products are attractive aspects of the present approach. The synthesized bindone and final product contains active methylene and this active site can be involved in further reactions to synthesize more complex heterocycles.

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Nickel supported on magnetic biochar as a highly efficient and recyclable heterogeneous catalyst for the one‐pot synthesis of spirooxindole‐dihydropyridines

Dong

Wang

Zhang

et al. 2022

Applied Organom Chemis

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Magnetic materials show promising applications in heterogeneous catalysis because of their ease of separation and good reusability. The present work reports the design, synthesis, and characterization of a novel magnetic biochar supported nickel catalyst. Fourier infrared spectroscopy (FT‐IR), powder X‐ray diffraction technology (XRD), scanning electron microscope (SEM), transmission electron microscope (TEM), and vibrating sample magnetometer (VSM) techniques were used for analyzing the prepared catalyst. The prepared catalyst exhibited excellent catalytic activity for synthesis of spirooxindole‐dihydropyridines derivatives by a one‐pot three‐component reaction of isatin, barbituric acid, and 6‐amino uracil or 1H‐pyrazol‐5‐amine. This new methodology demonstrated some important features, including high yields, lower loading of the catalyst, easy work‐up, and recyclability of the catalyst for a minimum of six times without an obvious decay of catalytic performance.

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An Efficient One‐Pot Four‐Component Synthesis of Some New Spirooxindole Dihydropyridine Using Alum as a Heterogeneous Green Catalyst

Cited by 14 publications

References 51 publications

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Synthesis of diverse spiro-imidazo pyridine-indene derivatives via acid-promoted annulation reaction of bindone and heterocyclic ketene aminals

Nickel supported on magnetic biochar as a highly efficient and recyclable heterogeneous catalyst for the one‐pot synthesis of spirooxindole‐dihydropyridines

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