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, Padmini C.; Saha, Soumik; Chatterjee, Amrita; Banerjee, Mainak

doi:10.1016/j.tetlet.2022.154209

Cited by 4 publications

(2 citation statements)

References 60 publications

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“…The microwave irradiation tender reactions above the boiling point of the solvents dramatically cut down the solvent volume and offer a huge acceleration of reaction rate benefiting the cost of the overall method. Microwave-assisted aza-Michael addition reactions in organic media are reported by us and others. , Traditionally, Michael addition requires a Lewis acid or a Lewis base to facilitate the reaction. However, there have been limited efforts to develop catalyst-free Michael reactions as well. , Encouraged by the need for a cost-effective and sustainable method for β-amino sulfones, we envisaged adopting a green synergy of microwave irradiation and water as a medium to develop a reagentless approach for these biologically important scaffolds.…”

Section: Introductionmentioning

confidence: 99%

“…33 The microwave irradiation tender reactions above the boiling point of the solvents dramatically cut down the solvent volume and offer a huge acceleration of reaction rate benefiting the cost of the overall method. Microwave-assisted aza-Michael addition reactions in organic media are reported by us 34 and others. 35,36 Traditionally, Michael addition requires a Lewis acid or a Lewis base to facilitate the reaction.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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Five-membered ring systems with O and N atoms

Cordero,

Giomi,

Machetti

2023

Progress in Heterocyclic Chemistry

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Dehydration in Water: A Reagentless and Straightforward Synthesis of Tetrahydroquinazolines under Microwave Irradiation or by Stirring at Room Temperature, and Their Subsequent Conversion into Quinazolines in a Micellar Medium

Panjikar,

Pinheiro,

Chatterjee

et al. 2024

Synthesis

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In a reagent-free, catalyst-free approach, a series of 2-substituted-1,2,3,4-tetrahydroquinazolines were synthesized by cyclo-condensation between various aldehydes and 2-aminobenzylamines via dehydration reaction in water. The reactions took just 2 min under microwave irradiation and proceeded well under stirring at room temperature affording tetrahydroquinazolines in high to excellent yields. The products were water-insoluble and isolated by simple filtration avoiding a conventional work-up step and offering an organic solvent-free process. Furthermore, terahydroquinazolines were efficiently oxidized to quinazolines in cetyltrimethylammonium bromide (CTAB) derived micellar media with cheap commercial bleaching solution (4% NaOCl in water) in high yields. This sustainable protocol has near zero E-factor.

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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

Cited by 4 publications

References 60 publications

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

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

Five-membered ring systems with O and N atoms

Dehydration in Water: A Reagentless and Straightforward Synthesis of Tetrahydroquinazolines under Microwave Irradiation or by Stirring at Room Temperature, and Their Subsequent Conversion into Quinazolines in a Micellar Medium

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