Synthesis of novel fluorescent benzo[a]pyrano[2,3-c]phenazine and benzo[a]chromeno[2,3-c]phenazine derivatives via facile four-component domino protocol

Saluja, Pooja; Chaudhary, Ankita; Khurana, Jitender M.

doi:10.1016/j.tetlet.2014.04.072

Cited by 42 publications

(11 citation statements)

References 23 publications

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“…The shoulder found at 138.06 ppm can be attributed to the carbon bound to the phenyl –SO 3 H group, and confirms the formation of the sulfonated polyaniline [ 38 , 39 , 40 ]. The ultraviolet–visible (UV–Vis, UV-1601, Shimadzu Corporation, Japan) spectrum of SAO ( Figure 3 D) shows a single peak at 285 nm, ascribed to the phenazine moieties formed [ 41 , 42 ] via strong π–π interactions [ 21 , 43 ]. The absence of peaks below 285 nm shows that the oligomers were not conjugated [ 44 ].…”

Section: Resultsmentioning

confidence: 99%

A Facile Synthesis Procedure for Sulfonated Aniline Oligomers with Distinct Microstructures

et al. 2018

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Well-defined sulfonated aniline oligomer (SAO) microstructures with rod and flake morphologies were successfully synthesized using an aniline and oxidant with a molar ratio of 10:1 in ethanol and acidic conditions (pH 4.8). The synthesized oligomers showed excellent dispersibility and assembled as well-defined structures in contrast to the shapeless aggregated material produced in a water medium. The synergistic effects among the monomer concentration, oxidant concentration, pH, and reaction medium are shown to be controlling parameters to generate SAO microstructures with distinct morphologies, whether micro sheets or micro rods.

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Section: Resultsmentioning

confidence: 99%

A Facile Synthesis Procedure for Sulfonated Aniline Oligomers with Distinct Microstructures

et al. 2018

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“…[32][33] In view of their potential applications in medicinal chemistry and materials chemistry, the development of efficient new methods for the synthesis of benzo[a]chromeno[2,3-c]phenazines and related scaffolds has elicited a lot of interest in recent years. [34][35] Although, a number of methods for the synthesis benzo[a] chromeno [2,3-c]phenazines have been reported in literature, these methods usually employ toxic or expensive catalysts, VOC based solvents or harsh/special reaction conditions, like the use of microwave irradiation with a catalyst, [36][37][38][39] use of strong acids [32,40] or high reaction temperatures. [33] Consequently, the development of an efficient, mild and operationally simple new eco-compatible method for the synthesis benzo[a]chromeno[2,3-c]phenazines that does not involve the use of toxic solvents or catalysts is urgently required.…”

Section: Introductionmentioning

confidence: 99%

Catalyst Free, Multicomponent Green Approach to Benzo[a]chromeno[2,3‐c]phenazines Using Glycerol as a Recyclable and Biodegradable Promoting Medium

et al. 2020

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A series of benzo[a]chromeno[2,3‐c]phenazine derivatives were synthesized through an efficient one‐pot, multicomponent eco‐friendly reaction of 2‐hydroxynaphthalene‐1,4‐dione, o‐phenylenediamines, cyclic 1,3‐dicarbonyl compounds and aromatic aldehydes, promoted by glycerol. To the best of our knowledge this is the first catalyst free protocol for synthesis of this important scaffold having potential applications in medicinal and materials chemistry. Other important attributes of the present method are the use of glycerol as a bio‐renewable and biodegradable reaction medium‐cum‐promoter, use of readily available substrates, mild reaction conditions, operational simplicity, broad substrate scope, short reaction time, easy workup, and high yields and atom efficiency, which makes the disclosed protocol a superior alternative to existing methods.

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“…Phenazine (I) which exists in natural and synthetic products, shows a variety of biological functions, including antimalarial ( Wang et al., 2011 ) antibacterial, antiparasitic ( Kour et al., 2013 ) fungicidal, ( Saluja et al., 2014 ) antitumor ( Khurana et al., 2012 ) and antiplatelet ( Shaterian and Mohammadnia, 2013 ) activities. In addition, chromenes (II) as an important class of compounds, widely present in plants, including edible vegetables and fruits ( Curini et al., 2006 ) also exhibit remarkable effects as pharmaceuticals, ( Yu et al., 2003 ) including antifungal ( Tangmouo et al., 2006 ) and antimicrobial activity ( Abd-el-aziz et al., 2004 ).…”

Section: Introductionmentioning

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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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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Synthesis of novel fluorescent benzo[a]pyrano[2,3-c]phenazine and benzo[a]chromeno[2,3-c]phenazine derivatives via facile four-component domino protocol

Cited by 42 publications

References 23 publications

A Facile Synthesis Procedure for Sulfonated Aniline Oligomers with Distinct Microstructures

A Facile Synthesis Procedure for Sulfonated Aniline Oligomers with Distinct Microstructures

Catalyst Free, Multicomponent Green Approach to Benzo[a]chromeno[2,3‐c]phenazines Using Glycerol as a Recyclable and Biodegradable Promoting Medium

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

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