Selective silver (I)-catalyzed four-component gram-scale synthesis of novel 1,4-disubstituted 1,2,3-triazole-sulfonamides under heterogeneous catalysis and microwave irradiation in water

Mahmoudi, Ayoub El; Masaoudi, Hind El; Tachallait, Hamza; Talha, Aicha; Arshad, Suhana; Benhida, Rachid; Jaber, B.; Benaïssa, Mohammed; Bougrin, Khalid

doi:10.1016/j.rechem.2022.100552

Cited by 5 publications

(5 citation statements)

References 72 publications

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“…The reaction exhibited an excellent yield, with 94% of the desired product 4 (Scheme 1). The structure of 4 was fully characterized by IR, 13 C, 1 H NMR, and LCMS spectra, and confirmed by single-crystal X-ray diffraction. Theoretical calculations, besides measuring the activity of molecules, give important information about many properties of these molecules [14].…”

Section: Synthesismentioning

confidence: 91%

Section: Synthesismentioning

confidence: 91%

“…NMR spectra were recorded on a Bruker AC 200 spectrometer (Bruker Biospin, Rheinstetten, Germany) at 200 MHz for 1 H NMR and 50 MHz for 13 C NMR in dry CDCl 3 solvent. Mass spectral analyses (ESI-MS) were recorded on an Agilent Technologies 1260 Infinity II LC/MSD (Agilent Technologies, Santa Clara, CA, USA) and the samples were diluted in acetonitrile.…”

Section: Methodsmentioning

confidence: 99%

“…The following supporting materials, containing 1 H, 13 C NMR, mass, and IR spectra (see Supplementary Materials Figures S1-S4) of the synthesized compound 4 can be downloaded online.…”

Section: Supplementary Materialsmentioning

confidence: 99%

“…Therefore, finding a green and efficient source for the synthesis of secondary sulfonamide derivatives should be a priority. Our research group has recently developed the synthesis of a new series of heterocyclic units bearing secondary sulfonamides using an eco-friendly protocol under ultrasound cavitation [12,13].…”

Section: Introductionmentioning

confidence: 99%

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2-(N-allylsulfamoyl)-N-propylbenzamide

El mahmoudi,

Chkirate,

Mokhi

et al. 2023

Molbank

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In this work, a new compound, 2-(N-allylsulfamoyl)-N-propylbenzamide, has been synthesized via a tandem one-pot reaction under sonication. The rotational orientations of the allylsulfamoyl and the amide groups in the title molecule, C13H18N2O3S, are partly determined by an intramolecular N—H···O hydrogen bond. In the crystal, a layer structure is generated by N—H···O and C—H···O hydrogen bonds plus C—H···π (ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to crystal packing are from H···H (59.2%), H···O/O···H (23.5%), and H···C/C···H (14.6%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G (d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 5.3828 eV.

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Section: Synthesismentioning

confidence: 91%

Section: Synthesismentioning

confidence: 91%

Section: Methodsmentioning

confidence: 99%

“…The following supporting materials, containing 1 H, 13 C NMR, mass, and IR spectra (see Supplementary Materials Figures S1-S4) of the synthesized compound 4 can be downloaded online.…”

Section: Supplementary Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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