One-pot solvent-free microwave-assisted aza-Michael addition reaction of acrylonitrile

Das, Parineeta; Devi, Nirmala; Пузари, Амрит

doi:10.1016/j.jics.2022.100411

Cited by 6 publications

(17 citation statements)

References 41 publications

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“…The synthesis of five acrylonitrile adducts namely n-propyliminobis-propionitrile (N1), nbutyliminobis-propionitrile (N2), n-hexyliminopropionitrile (N3), ndecyliminopropionitrile (N4) and n-dodecyliminopropionitrile (N5) was carried out by the efficacious aza-Michael addition reaction as outlined in Scheme 1. [51] Acrylonitrile of about 164.57 μL (2.5 mmol) was added to 1 mmol of the corresponding primary aliphatic Scheme 1. Synthesis of acrylonitrile adduct (N1) ChemistrySelect amines.…”

Section: Synthesis Of Acrylonitrile Adductsmentioning

confidence: 99%

“…n-propyliminobispropionitrile (N1), n-butyliminobis-propionitrile (N2), n-hexyliminopropionitrile (N3), n-decyliminopropionitrile (N4) acid and n-dodecyliminopropionitrile (N5). [51] To date a very few reports are available on the application of acrylonitrile adducts as a potent adsorbent for iron removal from water. Following greener approach acrylonitrile adducts were synthesized using microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%

“…The Aza-Michael adducts used for the study were synthesized under microwave irradiation using literature procedure. [51] In this study acrylonitrile adducts was discovered as iron ion adsorbate in water. The lone pair of electrons on the nitrogen atom of the nitrile group attracts the cationic pollutants like iron in aqueous solutions.…”

Section: Introductionmentioning

confidence: 99%

“…The reaction between several primary aliphatic amines and acrylonitrile has been carried out in our previous work to develop several acrylonitrile adducts viz. n‐propyliminobis‐propionitrile (N1), n‐butyliminobis‐propionitrile (N2), n‐hexyliminopropionitrile (N3), n‐decyliminopropionitrile (N4) acid and n‐dodecyliminopropionitrile (N5) [51] …”

Section: Introductionmentioning

confidence: 99%

“…Adsorption‐isotherm studies of such compounds are also limited which prompted us to undertake such study with a series of aza‐Michael adducts to evaluate the efficiency of such molecules for diverse applications, especially as an adsorbent. The Aza‐Michael adducts used for the study were synthesized under microwave irradiation using literature procedure [51] …”

Section: Introductionmentioning

confidence: 99%

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Acrylonitrile Adducts: An Efficient Adsorbent Media for Removal of Iron from Water

et al. 2022

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Present study establishes a series of acrylonitrile adducts as an effective adsorption media for removal of ferrous ion from water. Adduct synthesis was carried out following aza-Michael addition reaction between primary aliphatic amines and acrylonitrile under mild conditions. The synthesized products were characterised by FT-IR, ESI-MS and 1 H NMR spectroscopy and the particle size was analysed by DLS measurements. Adsorption isotherm study of the adducts showed prominent results. The positively charged iron ion interacts with negatively charged acrylonitrile adducts and forms a bulky structure which precipitates out from water. The most interesting feature of these compounds is its electron rich property which facilitates effective interaction with the positively charged iron ions present in water and thus imparting high adsorption capacity. Batch experiments were performed to figure out the best adsorption conditions. These studies were used to investigate the effects of various viable characteristics such as initial metal ion concentration, pH and contact time. The adsorption isotherm was well fitted by Langmuir model. The maximum adsorption capacity of acrylonitrile adducts for iron was recorded as 22.65 mg/g.

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Section: Synthesis Of Acrylonitrile Adductsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Acrylonitrile Adducts: An Efficient Adsorbent Media for Removal of Iron from Water

et al. 2022

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Microwave assisted rapid synthesis of bicyclo aza-sulfone derivatives from aldehydes via aldoxime formation followed by Michael addition-1,3-dipolar cycloaddition with divinyl sulfone in one-pot

Panjikar

Saha

Chatterjee

et al. 2022

Tetrahedron Letters

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Reagentless Chemistry “On-Water”: An Atom-Efficient and “Green” Route to Cyclic and Acyclic β-Amino Sulfones via aza-Michael Addition Using Microwave Irradiation

Saha,

Chatterjee,

Banerjee

2023

J. Org. Chem.

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A reagentless, catalyst-free, and sustainable methodology was developed for facile access to cyclic and acyclic β-amino sulfones "on-water" using a microwave. A variety of aromatic and aliphatic amines undergo double aza-Michael addition on the surface of the water with water-insoluble divinyl sulfones upon microwave irradiation at 150 °C for 10 min to mostly afford solid cyclic β-amino sulfones as easily separable products in excellent yields by simple filtration avoiding any workup steps. Thus, all atoms of the substrates are reflected in the product making it a 100% atom-efficient method. Both electron-rich and electron-deficient amines participated well in the reaction as well as good functional group tolerance was observed. The competitive experiments expectedly revealed faster reaction kinetics for electron-rich amines. The methodology was extended to acyclic β-amino sulfones by interacting phenyl/ethyl vinyl sulfones with various amines in a similar manner. Expectedly, the method afforded very low environmental factors (in a range of 0.05−0.5) and a high Ecoscale score (up to 94). In an attempt toward sustainable development, this reagent-free, metal-free, organic solvent-free, cost-effective protocol is certainly a viable alternative to the available methods for β-amino sulfones.

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One-pot solvent-free microwave-assisted aza-Michael addition reaction of acrylonitrile

Cited by 6 publications

References 41 publications

Acrylonitrile Adducts: An Efficient Adsorbent Media for Removal of Iron from Water

Acrylonitrile Adducts: An Efficient Adsorbent Media for Removal of Iron from Water

Microwave assisted rapid synthesis of bicyclo aza-sulfone derivatives from aldehydes via aldoxime formation followed by Michael addition-1,3-dipolar cycloaddition with divinyl sulfone in one-pot

Reagentless Chemistry “On-Water”: An Atom-Efficient and “Green” Route to Cyclic and Acyclic β-Amino Sulfones via aza-Michael Addition Using Microwave Irradiation

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