Synthetic routes for phenazines: an overview

Chaudhary, Ankita; Khurana, Jitender M.

doi:10.1007/s11164-017-3152-8

Cited by 43 publications

(26 citation statements)

References 114 publications

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“… Entry Cat. & loading Solvent Condition Time (min) Yield (%) Reference 1 Acetic acid (5% mol) H 2 O MW 15 89 ( Wang et al., 2011 ) 2 PEG 400 (10% mol) EtOH Reflux 120 92 ( Khurana et al., 2012 ) 3 Ionic Liquid (5% mol) H 2 O Reflux 10 96 ( Shaterian and Mohammadnia, 2013 ) 4 Ch/ZnO (20 Mg) EtOH MW 5 93 This work 5 [Co (TPPABr)]CBr (20 Mg) EtOH Reflux 45 91 ( Dashteh et al., 2019 ) 6 Fe 3 O 4 @SiO 2 -TCT-Theophylline (1.1% mol) EtOH Reflux 20 95 ( Esmaeilpour et al., 2018 ) 7 Caffeine (20%mol) - MW 10 90 ( Chaudhary and Khurana, 2018 ) Bold signifies the present work. …”

Section: Resultsmentioning

confidence: 97%

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Preparation of α-chitin-based nanocomposite as an effective biocatalyst for microwave aided domino reaction

Abolghassem

Molaei

Javanshir

2019

Heliyon

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In this paper, chitin (Ch) was extracted by an optimized method from cuttlebone of the Persian Gulf cuttlefish (Sepiidae, Cephalopoda). The extracted chitin was characterized by Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD) and thermal gravimetric analysis (TGA) which showed that the extracted chitin was in alpha form. The degree of N-acetylation (DA) and degree of substitution (DS) of α-chitin were calculated using titration method and FTIR spectroscopy and found to be 80–82% and 19.57 respectively. The α-Chitin was used as biomolecules for the preparation of nanostructured Ch/ZnO via a hydrothermal method. The obtained nanocomposite was characterized using FT-IR, XRD, scanning electron microscopy (SEM), and energy-dispersive X-ray spectroscopy (EDX) analysis. The antimicrobial aspect of Ch/ZnO nanocomposite was previously proposed. In this paper, attempt was made to add the catalytic feature to these traits. For this purpose, the nanostructured Ch/ZnO was used as reusable nanocatalyst in the green and efficient synthesis of Benzo[a]pyrano(2,3-c)phenazine derivatives thru a four components microwave aided domino reaction. Eco-friendly, easy work up and separation of the nanostructured catalyst are some of the highlighted features this protocol.

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Section: Resultsmentioning

confidence: 97%

“…This comparison was made on 2-hydroxynaphthalene-1,4-dione with O-phenylenediamine, 4-chlorobenzaldehyde, and malononitrile as the model reaction. (Chaudhary and Khurana, 2018) Bold signifies the present work.…”

Section: Comparisons With Other Reportsmentioning

confidence: 99%

Preparation of α-chitin-based nanocomposite as an effective biocatalyst for microwave aided domino reaction

Abolghassem

Molaei

Javanshir

2019

Heliyon

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“…[8,[12][13][14] The major advantages of multicomponent reactions are one-pot synthesis, high atom economy and time-saving without isolation of intermediates or generating byproducts. [14][15][16][17][18][19] In particular, Phenazines and chromenes have attracted increasing attention in drug discovery and medicinal chemistry which can be synthesized by a one-pot two-steps procedure. [8,[18][19][20] These compounds have been reported as biological active species which involve anticancer, antifungal, antiplasmodial, antimalarial, antibacterial, cancer chemopreventive, antiparasitic and antichagasagen activities.…”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16][17][18][19] In particular, Phenazines and chromenes have attracted increasing attention in drug discovery and medicinal chemistry which can be synthesized by a one-pot two-steps procedure. [8,[18][19][20] These compounds have been reported as biological active species which involve anticancer, antifungal, antiplasmodial, antimalarial, antibacterial, cancer chemopreventive, antiparasitic and antichagasagen activities. [19] Among the wide range of N-containing heterocyclic compounds, the pyrazolones and bispyrazolones were paid much attention for their various biological activities, such as antitumor, [21] antiinflammatory, [22] antifilarial agents, [23] dyes, [24] pesticides, [14] selective COX-2 inhibitory, [25] antibacterial [23] and fungicides.…”

Section: Introductionmentioning

confidence: 99%

Zirconium@guanine@MCM‐41 nanoparticles: An efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component tandem Knoevenagel condensation–Michael addition–cyclization Reactions

Nikoorazm

Mohammadi

Khanmoradi

2020

Applied Organom Chemis

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MCM-41-supported nanoscale guanine bonded with Zr (IV) was prepared using sol-gel method and characterized by FT-IR, Raman, XRD, BET, TGA, EDX, ICP, AAS, X-Ray mapping, SEM and TEM techniques. This compound was employed as an efficient, chemoselectivity and green heterogeneous catalyst in order to prepare a series of benzo[a]benzo[6,7]chromeno[2,3-c] phenazine and spiro[benzo[a]benzo[6,7]chromeno[2,3-c] phenazine] derivatives by one-pot, four-component domino reaction from the 2-hydroxy-1,-4-naphthoquinone, benzene-1,2-diamines, 2-hydroxy-1,4-naphthoquinone and carbonyl compounds in PEG, at 100 C and, also, Bis (pyrazolyl) methane derivatives using aldehydes and 3-Methyl-1-phenyl-5-pyrazolone in ethanol under reflux condition. Results indicated that all products were synthesized in short reaction times and high yields in the ranges 78-99%. The Zr-guanine-MCM-41 can be recycled four runs without any significant loss of its catalytic activity. In addition, the stability of the catalyst was confirmed by metal leaching, heterogeneity tests, SEM and FT-IR techniques. K E Y W O R D S benzo[a]benzo[6,7]chromeno[2,3-c]phenazines, Bis (pyrazolyl)methanes, Spiro[benzo[a] benzo[6,7]chromeno[2,3-c] phenazine], Tandem Knoevenagel condensation-Michael additioncyclization, Zr-guanine-MCM-41

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“…[14,15,[25][26][27][28][29][30] Benzo [a] pyrano [2, 3-c] phenazine and 4,4 0 -(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols) compounds have a great potential in order to be applied in biological and pharmaceutical systems such as antifungal, anticancer, antiplasmodial, antimalarial, antibacterial, antiparasitic, anticancer and antichagasagen systems. [27,28,[31][32][33][34][35][36][37][38][39] However, synthesis of these useful compounds needs a better method which should be in agreement with green chemistry rules.…”

Section: Introductionmentioning

confidence: 99%

Guanine‐La complex supported onto SBA‐15: A novel efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component Tandem Knoevenagel condensation–Michael addition–cyclization Reactions

Nikoorazm

Khanmoradi

Mohammadi

2020

Applied Organom Chemis

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In this work, we present a simple, environmentally‐friendly and economical route for the preparation of a novel lanthanum (III) organometallic complex immobilized onto a highly stable mesoporous silica SBA‐15 (La‐guanine@SBA‐15) using an inexpensive and simple method and available materials. This mesoporous heterogenized complex was comprehensively characterized using FT‐IR, XRD, EDS, ICP, MAP, SEM, TGA and BET techniques. The catalytic activity of this mesoporous material was studied in one‐pot multi‐component tandem Knoevenagel condensation–Michael addition–cyclization reactions in order to prepare a series of benzo [a] pyrano [2, 3‐c] phenazine and 4,4′‐(arylmethylene)‐bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ols) derivatives under green conditions. This catalyst exhibited highly recoverable and recyclable features in consecutive reaction runs. Besides, the products were obtained in high yields and short reaction times. In this sense, simple preparation of the catalyst from the commercially available materials, simple operation, high catalytic activity, short reaction times, high yields and the use of green reaction conditions in the mentioned organic synthesis are the most significant advantages of this protocol. In addition, this nanocatalyst was easily recovered, using simple filtration, and reused several times without significant loss of its catalytic efficiency. Moreover, the leaching, heterogeneity and stability of La‐guanine@SBA‐15 were studied by hot filtration test and ICP technique. Finally, stability of the catalyst after recycling was confirmed by SEM and FT‐IR techniques.

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Synthetic routes for phenazines: an overview

Cited by 43 publications

References 114 publications

Preparation of α-chitin-based nanocomposite as an effective biocatalyst for microwave aided domino reaction

Preparation of α-chitin-based nanocomposite as an effective biocatalyst for microwave aided domino reaction

Zirconium@guanine@MCM‐41 nanoparticles: An efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component tandem Knoevenagel condensation–Michael addition–cyclization Reactions

Guanine‐La complex supported onto SBA‐15: A novel efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component Tandem Knoevenagel condensation–Michael addition–cyclization Reactions

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