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

Abstract 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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l-proline N-sulfonic acid-functionalized magnetic nanoparticles: a novel and magnetically reusable catalyst for one-pot synthesis of 3,4-dihydropyrimidine-2-(1H)-thiones under solvent-free conditions

RSC Advances ◽

10.1039/c6ra10558k ◽

2016 ◽

Vol 6 (64) ◽

pp. 59343-59351 ◽

Cited By ~ 10

Author(s):

M. Afradi ◽

N. Foroughifar ◽

H. Pasdar ◽

H. Moghanian

Keyword(s):

Magnetic Nanoparticles ◽

Sulfonic Acid ◽

Acid Catalyst ◽

Solvent Free ◽

Reusable Catalyst ◽

One Pot ◽

One Pot Synthesis ◽

Solvent Free Conditions ◽

Functionalized Magnetic Nanoparticles

Synthesis, characterization and utilization of the l-proline N-sulfonic acid-functionalized magnetic nanoparticles as a novel magnetically reusable acid catalyst for the synthesis of 3,4-dihydropyrimidine-2-[1H]thione derivatives is reported.

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Use of Nanomagnetic Sulfated Zirconia (Fe3 O4 @ZrO2 /SO4 2− ) as Sustainable Heterogeneous Acid Catalyst for Synthesis of Spiroheterocycles under Solvent-Free Conditions

ChemistrySelect ◽

10.1002/slct.201702422 ◽

2017 ◽

Vol 2 (34) ◽

pp. 11055-11061 ◽

Cited By ~ 9

Author(s):

Yogesh Kumar Tailor ◽

Sarita Khandelwal ◽

Ram Gopal ◽

Esha Rushell ◽

Anamika Prajapati ◽

...

Keyword(s):

Sulfated Zirconia ◽

Acid Catalyst ◽

Solvent Free ◽

Solvent Free Conditions ◽

Heterogeneous Acid Catalyst

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Synthesis of Acetals and Ketals Catalyzed by H4SiW6Mo6O40/SiO2

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.430-432.289 ◽

2012 ◽

Vol 430-432 ◽

pp. 289-292

Author(s):

Shui Jin Yang ◽

Li Yu ◽

Yong Kui Huang ◽

Guo Bin Duan

Keyword(s):

High Activity ◽

Sol Gel ◽

Acid Catalyst ◽

Reusable Catalyst ◽

Reaction Parameters ◽

Catalytic Application ◽

Heterogeneous Acid Catalyst ◽

Gel Technique ◽

Optimized Conditions

Heterogeneous acid catalyst, H4SiW6Mo6O40/SiO2 was synthesized by a sol-gel technique. Catalytic application of the catalyst for synthesis of acetals and ketals were tested. The variation of different reaction parameters on the yield of acetals and ketals were also studied. The yields of acetals and ketals can reach 80.0%~96.9% at the optimized conditions. The high activity and stability of the catalyst is well retained after 4 runs. The results reveal that the H4SiW6Mo6O40/SiO2 catalysis is a novel, effective and reusable catalyst for synthesizing actetals and ketals.

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Synthesis of tricyanomethanesulfonic acid as a novel nanostructured and recyclable solid acid: application at the synthesis of biological henna-based chromenes

Canadian Journal of Chemistry ◽

10.1139/cjc-2016-0534 ◽

2017 ◽

Vol 95 (5) ◽

pp. 560-570 ◽

Cited By ~ 3

Author(s):

Mohammad Ali Zolfigol ◽

Ardeshir Khazaei ◽

Saied Alaie ◽

Saeed Baghery

Keyword(s):

Electron Microscopy ◽

Solid Acid ◽

Solid Acid Catalyst ◽

Acid Catalyst ◽

Aromatic Aldehydes ◽

Reusable Catalyst ◽

Thermal Gravimetric ◽

One Pot ◽

Solvent Free Conditions ◽

Diffraction Patterns

A novel and unique nanostructured solid acid, namely tricyanomethanesulfonic acid (TCMS), was designed, synthesized, and attained as an ecofriendly, reusable catalyst for the one-pot three-component synthesis of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene derivatives from the reaction between aromatic aldehydes, 2-hydroxynaphthalene-1,4-dione (henna), and malononitrile under solvent-free conditions at room temperature with good to excellent yields and a short reaction time. The TCMS catalyst was prepared and fully characterized by FTIR, 1H NMR, 13C NMR, mass, X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermal gravimetric (TG), and derivative thermal gravimetric (DTG) analyses. The nanostructured solid acid catalyst was simply recycled at least eight times without any loss of catalytic activity. This process is improved as a safe and appropriate procedure for the synthesis of 2-amino-3-cyano-4-aryl-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromenes using an environmentally friendly and green recyclable catalyst. Thus, TCMS is a good candidate for the synthesis of new molecular organic frameworks and gelators.

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A Green Synthesis of 1,5-Benzodiazepines using Reusable-Heterogeneous Silica Sulfuric Acid Catalyst under Solvent-Free Conditions and their Antileukemic Activity

Asian Journal of Chemistry ◽

10.14233/ajchem.2021.23103 ◽

2021 ◽

Vol 33 (5) ◽

pp. 1006-1012

Author(s):

Kachigere B. Harsha ◽

Chandagirikoppal V. Kavitha ◽

Toreshettahally R. Swaroop ◽

Shobith Rangappa ◽

Kanchugarakoppal S. Rangappa

Keyword(s):

Sulfuric Acid ◽

Cell Lines ◽

Acid Catalyst ◽

Solvent Free ◽

Reusable Catalyst ◽

G1 Arrest ◽

Silica Sulfuric Acid ◽

Hydrogen Atoms ◽

Solvent Free Conditions ◽

Sulfuric Acid Catalyst

1,5-Benzodiazepine derivatives are readily assembled from o-phenylene diamine and ketones containg α-hydrogen atoms by means of simple cyclocondensation via sp3 C-H activation promoted by an efficient heterogeneous silica sulfuric acid catalyst. Eco-friendliness, good yields, easy workup, reusable catalyst, short reaction times, high atom economy and solvent-free conditions are the noteworthy features of this protocol. These benzodiazepines are chosen for the evaluation of antiproliferative activity against different leukemia cell lines. Among the investigated compounds, 3g is the best antiproliferative agent against all the cell lines tested. Also, current preliminary analysis showed that compound 3g phosphorylates ERK1/2 and induces G1 arrest in K562 cells

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Multisulfonate hyperbranched polyglycerol functionalized graphene oxide as an efficient reusable catalyst for green synthesis of benzo[a]pyrano-[2,3-c]phenazines under solvent-free conditions

RSC Advances ◽

10.1039/c8ra10180a ◽

2019 ◽

Vol 9 (13) ◽

pp. 7400-7410 ◽

Cited By ~ 2

Author(s):

Hossein Naeimi ◽

Maryam Farahnak Zarabi

Keyword(s):

Graphene Oxide ◽

Green Synthesis ◽

Acid Catalyst ◽

Solvent Free ◽

Reusable Catalyst ◽

Hydroxyl Groups ◽

Functionalized Graphene ◽

Functionalized Graphene Oxide ◽

Solvent Free Conditions ◽

Hyperbranched Polyglycerol

A novel acid catalyst was prepared based on growing hyperbranched polyglycerol (HPG) on the surface of graphene oxide. Then, the hydroxyl groups of HPG on graphene oxide were functionalized by sulfonate groups to form an acid catalyst.

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Efficient Synthesis of 2-amino-4H-chromene Derivatives in the Presence of Piperazine-functionalized Fe3O4/SiO2 Magnetic Nanoparticles as a New Heterogeneous Reusable Catalyst Under Solvent-free Conditions

Letters in Organic Chemistry ◽

10.2174/1570178611666140304000656 ◽

2014 ◽

Vol 11 (6) ◽

pp. 432-439 ◽

Cited By ~ 10

Author(s):

Akbar Mobinikhaledi ◽

Hassan Moghanian ◽

Zeinab Souri

Keyword(s):

Magnetic Nanoparticles ◽

Solvent Free ◽

Reusable Catalyst ◽

Efficient Synthesis ◽

Solvent Free Conditions

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Synthesis and Antimicrobial activities of Some Polyphenol compounds by Nano ZnO-TBAB as a Heterogeneous Catalytic Media

Letters in Organic Chemistry ◽

10.2174/1570178617999200517131353 ◽

2020 ◽

Vol 17 ◽

Author(s):

Rahele Bargebid ◽

Ali Khalafi-Nezhad ◽

Kamiar Zomorodian ◽

Leila Zamani ◽

Ali Ahmadinejad ◽

...

Keyword(s):

Antibacterial Activities ◽

Antimicrobial Activities ◽

Reusable Catalyst ◽

Nano Zno ◽

Antifungal Activities ◽

Chemical Structures ◽

Heterogeneous Catalytic ◽

Solvent Free Conditions ◽

New Compounds ◽

Derivatives Of

Introduction: Mannich reaction is a typical example of a three-component condensation reaction and the chemistry of Mannich bases has been the matter of search by researchers. Here an efficient procedure for the synthesis of some new Mannich derivatives of simple phenols is described. Methods: In this procedure a microwave-assisted and solvent less condensation were done between different phenols, secondary amines and paraformaldehyde. The reactions proceed in the presence of catalytic amount of nano ZnO and tetrabutylammonium bromide (TBAB) in excellent yields. 10 new compounds were synthesized (A1-A10). Chemical structures of all new compounds were confirmed by different spectroscopic methods. We optimized the chemical reactions in different conditions. Optimization reactions were done in the presence of different mineral oxides, different amount of TBAB and also different solvents. Nano ZnO and TBAB in catalytic amounts and solvent free conditions were the best conditions. All the synthesized compounds were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized compounds were evaluated against some Candida, filaments fungi, gram positive and gram negative bacteria by broth micro dilution method as recommended by CLSI. Results: The result showed that compounds A2, A3 and A4 against most of the tested Candida species and compounds A5 and A7 against C. parapsilosis and C. tropicalis, exhibited considerable antifungal activities. Also Compounds A8 and A10 showed desirable antifungal activities against C. neoformance and C. parapsilosis, respectively. The antibacterial activities of the synthesized compounds were also evaluated. Compounds A6 - A10 against E. Fecalis and compounds A5, A7, A9 and A10 against P. aeruginosa showed desirable antibacterial activities. Discussion: We have synthesized some new Mannich adducts of poly-hydroxyl phenols in the presence of nano-ZnO as a reusable catalyst, with the hope of discovering new lead compounds serving as potent antimicrobial agents. The advantages of this method are generality, high yields with short reaction times, simplicity, low cost and matching with green chemistry protocols. The antimicriobial studies of Mannich derivatives of phenols showed desirable results in vitro.

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