Synthesis of 1,5-Benzodiazepine and Its Derivatives by Condensation Reaction Using H-MCM-22 as Catalyst

Majid, Sheikh Abdul; Khanday, Waheed Ahmad; Tomar, Radha

doi:10.1155/2012/510650

Cited by 31 publications

(15 citation statements)

References 25 publications

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“…251 Multiple synthetic pathways are described toward benzodiazepines, which also include routes involving MCRs. 147,252−263 Because of the privileged scaffold character of tetrazoles and benzodiazepines, several researchers designed synthetic strategies to combine the two heterocycles. 264…”

Section: Multicomponent Reactions For the Synthesis Of Tetrazolesmentioning

confidence: 99%

Tetrazoles via Multicomponent Reactions

2019

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Tetrazole derivatives are a prime class of heterocycles, very important to medicinal chemistry and drug design due to not only their bioisosterism to carboxylic acid and amide moieties but also to their metabolic stability and other beneficial physicochemical properties. Although more than 20 FDA-approved drugs contain 1H- or 2H-tetrazole substituents, their exact binding mode, structural biology, 3D conformations, and in general their chemical behavior is not fully understood. Importantly, multicomponent reaction (MCR) chemistry offers convergent access to multiple tetrazole scaffolds providing the three important elements of novelty, diversity, and complexity, yet MCR pathways to tetrazoles are far from completely explored. Here, we review the use of multicomponent reactions for the preparation of substituted tetrazole derivatives. We highlight specific applications and general trends holding therein and discuss synthetic approaches and their value by analyzing scope and limitations, and also enlighten their receptor binding mode. Finally, we estimated the prospects of further research in this field.

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Section: Multicomponent Reactions For the Synthesis Of Tetrazolesmentioning

confidence: 99%

Tetrazoles via Multicomponent Reactions

2019

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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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“…Mesoporous materials such as H-MCM-22 has also been used as effective catalysts in the condensation reaction between o-phenylenediamine and symmetrical and unsymmetrical ketones in acetonitrile at room temperature, in shorter reaction times [163]. The authors studied in detail the effect of the catalyst and the catalyst concentration on the reaction.…”

Section: Figure 19mentioning

confidence: 99%