Nano silica-bonded N-propylsulfamic acid as an efficient and environmentally benign catalyst for the synthesis of 1,5-benzodiazepines

Tarannum, Saima; Siddiqui, Zeba N.

doi:10.1007/s00706-016-1775-x

Cited by 9 publications

(3 citation statements)

References 48 publications

(27 reference statements)

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“…The FT-IR spectrum of PVC-EDA-SO3H shows the absorption band at 3430 cm -1 is attributed to the OH group stretching vibrations of SO3H group, and the peak at about 1110 cm −1 is attributed to the typical vibration bands of SO3 -stretching and the stretching absorption modes of O=S=O of supported SO3H group. Notably, the absorption peak at 1652 cm -1 corresponded to the bending vibration of the N-H bond suffered a slight shift to the direction of low wavenumber after chlorosulfonation of PVC-EDA, these finding confirm that the sulfonic groups are successfully grafted on PVC-EDA by chlorosulfonation reaction [44][45][46][47]. These characteristic vibrations clearly indicate the formation of desired catalytic system.…”

Section: Ft-irsupporting

confidence: 53%

Sulfamic acid functionalized PVC: a remarkably efficient heterogeneous reusable catalyst for the acid-catalyzed reactions

Wang,

Zhang,

Liu

et al. 2023

Res Chem Intermed

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Sulfamic acid functionalized polyvinyl chloride catalysts (PVC-N-SO3H, N=EDA, DTA, TTA, TPA, PHA) were prepared as efficient heterogeneous solid acid catalysts via two-steps treatment processes. The prepared catalysts were characterized by X-ray diffraction analysis (XRD), TG thermograms/derivative thermogravimetric (TG/DTG), transmission electron microscope (TEM), elemental mappings and energy-dispersive spectroscopy analyses (STEM-EDS), and FT-IR measurements (FT-IR) as well as acid-base back-titration. The acetalization of aldehydes (ketones) and alcohols to acetal (ketal) was selected to evaluate the acid catalytic performance of PVC-N-SO3H. The results showed that PVC-EDA-SO3H exhibit excellent activity and reusability due to its highly exposed sulfonic acid sites, high surface acid density (2.28 mmol g -1 ) for the conversion of aldehydes (ketones) to acetal (ketal). This new solid acid has obvious advantages in reusability and catalytic activity over traditional homogeneous concentrated sulfuric acid and heterogeneous sulfonated resin catalysts. Furthermore, PVC-EDA-SO3H exhibited an excellent catalytic performance in the synthesis of 12 acetals (ketals) as well as a good compatibility in the hydroxyalkylation of phenol with formaldehyde to bisphenol F (BPF) and the esterification reaction of oleic acid and methanol to biodiesel. More importantly, it could also be recovered easily and used repeatedly at least nine times without an obvious decrease in the activity.

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Section: Ft-irsupporting

confidence: 53%

Sulfamic acid functionalized PVC: a remarkably efficient heterogeneous reusable catalyst for the acid-catalyzed reactions

Wang,

Zhang,

Liu

et al. 2023

Res Chem Intermed

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“…Benzodiazepines have been usually synthesized by the condensation of 1,2-phenyldiamines with β-dicarbonyl compounds using different inorganic or organic acid promoters, e.g., polyphosphoric acid [21], acetic acid [22], HY zeolite [23], p-toluenesulfonic acid [24], N-propylsulfamic acid/nanosilica [25], indium tribromide [26], zinc montmorillonite [27], sulfated zirconia [28], MCM-22 zeolite [29], heteropolyacids [30,31], among others [32,33].…”

Section: Introductionmentioning

confidence: 99%

Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines

Muñoz

Pasquale

Sathicq

et al. 2019

Green Processing and Synthesis

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The volcanic ash from the Andes mountain range (Puyehue-Cordon Caulle volcanic complex situated in western South America on the Argentinean-Chilean border) was used as heterogeneous acid catalyst in the suitable synthesis of 3H-1,5-benzodiazepines. The natural ashes were classified according to their particle size to generate the different catalytic materials. The catalysts were characterized by powder X-ray diffraction (XRD), scanning electron microscopy (SEM) with energy dispersive spectroscopy (EDS), vibrational spectroscopies (FT-IR and Raman), and textural properties were determined by N2 adsorption (SBET). Potentiometric titration with n-butylamine was used to determine the acidic properties of the catalytic materials. Several 3H-1,5-benzodiazepines were obtained by reaction of o-phenylenediamine and substituted 1,3-diphenyl-1,3-propanedione in solvent-free conditions, giving good to excellent yields of a variety benzodiazepines. The method was carried out in environmentally friendly conditions and it was operationally simple. The volcanic ash resulted in a safe and recyclable catalyst.

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“…Three-component condensation of 3-formylchromones 1, o-phenylenediamine, and 3-acetyl-4-hydroxycoumarin catalyzed by nano silica-supported N-propylsulfamic acid resulted in 4-hydroxy-3-[2-(4-oxo-4Hchromen-3-yl)-2,3-dihydro-1H-benzo[b] [1,4]diaze pin-4-yl]-2H-chromen-2-ones 151. 154 The use of dimed one as a CH acidic component gave rise to the fused 3,3-dimethyl-11-(4-oxo-4H-chromen-3-yl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e] [1,4]diazepin-1-ones 152. 155 The reaction requires no solvent and can be also catalyzed by silica-supported Fe(OTs) 3 .…”

Section: Isofl Avone Hetero Analogs With Seven-membered Heterocyclesmentioning

confidence: 99%

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

et al. 2021

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The review is focused on recent developments of chemistry of synthetic analogs of natural compounds, isofl avone and homoisofl avone. The possible synthetic strategies to access heterocyclic analogs of these compounds starting from readily available 3-formylchromone and its derivatives (3-cyanochromone, 2-amino-3-formylchromone) and products of its condensation with simplest Cand N-nucleophiles are discussed. The structural features of the reaction products that depend on the nature of the reaction medium, structure of the starting compounds, and reagent ratio are considered. Particular attention is given to the application of the modern strategies of organic synthesis, namely green chemistry approaches, click reactions, domino reactions, etc. Examples of compounds of this group most promising for clinical application due to wide and pronounced pharmacological eff ects are given.

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Nano silica-bonded N-propylsulfamic acid as an efficient and environmentally benign catalyst for the synthesis of 1,5-benzodiazepines

Cited by 9 publications

References 48 publications

Sulfamic acid functionalized PVC: a remarkably efficient heterogeneous reusable catalyst for the acid-catalyzed reactions

Sulfamic acid functionalized PVC: a remarkably efficient heterogeneous reusable catalyst for the acid-catalyzed reactions

Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

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