Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process

Zaharani, Lia; Khaligh, Nader Ghaffari; Mihankhah, Taraneh; Johan, Mohd Rafie

doi:10.1007/s11030-020-10092-4

Cited by 17 publications

(5 citation statements)

References 62 publications

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“…It was discovered that the copper (I)/bipyridine reagent system in dry organic solvents promotes the Petasis reaction. The synthesis of 2-amino-4H-benzo[b]pyrans (40) was achieved from a 3CR of 4-chlorobenzaldehyde (a), malononitrile (b), and 5,5-dimethyl-1,3-cyclohexadione (dimedone) (c) using mesoporous poly-melamine-formaldehyde (mPMF) as a heterogeneous catalyst for one hour at room temperature, as shown in Scheme 35 [54]. The reaction conditions also adhered to green chemistry principles after using the planetary ball milling process at room temperature with no solvents.…”

Section: Solid-phase Synthesismentioning

confidence: 99%

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Mohlala¹,

Rashamuse²,

Coyanis³

2023

Preprint

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Multicomponent reactions (MCRs) have been used for more than a century; since their discovery in 1850 by Strecker. To date, MCRs route is regarded as a beneficial strategy due to its capacity to quickly produce molecular diversity and structural complexity of interest for a variety of applications. Despite having famous MRCs such as the Ugi, Passerini, Biginelli, and Hantzsch, this re-view portrays the importance of MCRs in the synthesis of desired products towards applications such as medicinal purposes, sustainable chemistry, and polymerisation. MCRs provide ad-vantages such as reducing the number of sequential multiple reactions to one step, atom economy, recyclable catalysts, mild conditions, preventing waste and reduce solvent use.

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Section: Solid-phase Synthesismentioning

confidence: 99%

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Mohlala¹,

Rashamuse²,

Coyanis³

2023

Preprint

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“…Zaharani et al [118] synthesized a nitrogen rich heterogeneous bifunctional catalyst, porous poly-melaamineformaldehyde (mPMF) for benzopyrans. About 20 mg S C H E M E 4 1 Synthesis of bispyran derivatives using piperazine catalyst was used in a milling jar having 6 milling balls at 600 rpm for the reaction at RT.…”

Section: Polymer Supported Synthesismentioning

confidence: 99%

An overview of recent advances in the catalytic synthesis of substituted pyrans

Agarwal¹,

Sethiya²,

Soni³

et al. 2022

Applied Organom Chemis

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Substituted pyrans (4H‐Chromenes) are the most significant structural scaffolds in synthetic and medicinal chemistry. They are found in an array of natural products, medicines, and phytochemical compounds, bearing an explicit of pharmacological activities. The structural importance of substituted pyrans has elicited a huge upsurge in the field of synthesis and biology. Different synthetic approaches of 4H‐chromene scaffolds have been discussed systematically to emphasize their significance in the scientific world. The present article summarizes the different synthetic strategies of substituted pyran derivatives via acid‐base catalysis, ionic liquids, nanomaterials, deep eutectic solvents, bio‐based, visible light, metal catalyzed, and so forth developed in the last decade. Moreover, this article will definitely contribute to the scientific world for developing synthetically and biologically important pyran analogs.

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“…Recognizing such prominent features and therapeutic potential of 2-amino-3-cyano-4 H -chromene, the synthesis of heterocycles possessing chromene moiety is of increasing scientific and academic interest. Accordingly, several synthetic methods to realize this heterocycle by using different catalytic systems such as heterogeneous or homogeneous catalysts 49 – 51 , magnetic nanoparticles 52 – 54 , ionic liquids 55 – 57 , metal complex 58 – 60 , organocatalysts 61 – 64 , polymers 65 , carbon quantum dots 66 , organic–inorganic hybrids 67 , metal–organic frameworks 68 , deep eutectic solvents 69 , as well as catalyst-free conditions 70 , 71 were developed in the last decades.…”

Section: Introductionmentioning

confidence: 99%

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry

Borah

Swain

Patat

et al. 2023

Sci Rep

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Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4H-chromenes, tetrahydrospiro[chromene-3,4′-indoline], 2,2′-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tetrahydro-1H-xanthen-1-one by employing the reactivity of 5,5-dimethylcyclohexane-1,3-dione/cyclohexane-1,3-dione with TsOH⋅H2O as Brønsted acid catalyst under water-assisted grinding conditions at ambient temperature. The ability to accomplish multiple C–C, C=C, C–O, and C–N bonds from readily available starting materials via a domino multicomponent strategy in the absence of metal-catalyst as well as volatile organic solvents with an immediate reduction in the cost of the transformation without necessitates complex operational procedures, features the significant highlights of this approach. The excellent yield of the products, broad functional group tolerances, easy set-up, column-free, scalable synthesis with ultralow catalyst loading, short reaction time, waste-free, ligand-free, and toxic-free, are other notable advantages of this approach. The greenness and sustainability of the protocol were also established by demonstrating several green metrics parameters.

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Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process

Cited by 17 publications

References 62 publications

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

Multicomponent Reactions as an Efficient and Facile Alternative Route in Organic Synthesis and Applications

An overview of recent advances in the catalytic synthesis of substituted pyrans

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry

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