Abstract:The 1,6‐disubstituted‐ and 4,6‐disubstituted‐11‐aza‐5H‐benzo[a]phenoxazin‐5‐one as well as 6‐substituted‐11‐aza‐5H‐pyrido[a]phenoxazin‐5‐one derivatives were prepared by the condensation of 2‐amino‐3‐hydroxypyridine with 5‐substituted‐2,3‐dihalogeno‐1,4‐naphthoquinones and 6,7‐dibromo‐5,8‐quinolinequinone respectively. The resulting compounds were subjected to reduction, acetylation, dehalogenation and reaction with aniline.
“…Nan’ya et al reported the synthesis of 11-aza-5 H -benzo[a]phenoxazin-5-one derivatives, 59 by the condensation of 5-substituted-2,3-dihalogeno-1,4–naphthoquinone, 58 with 2-amino-3-hydroxypyridine, 55 in the presence of potassium acetate and in benzene/ethanol medium (Scheme 19 a) [ 56 ]. Ishii reported the acid-catalysed synthesis of pyrido[3,2-a]phenoxazine, 61 which was obtained by the condensation of 2-aminophenol and 4,6-dihydroxyquinoline-5,8-dione, 60 (Scheme 19 b) [ 57 ].…”
Section: Synthetic Methods To Prepare Several Phenoxazine Derivativesmentioning
confidence: 99%
“…Okafor et al reported the synthesis of another phenoxazine-containing compound, 6-chlorobenzo[a]-11-azaphenoxazine-5-one, 63 by refluxing 2,3-dichloro-1,4-naphthoquinone, 62 with 2-amino-3-pyridinol, 55 in chloroform and anhydrous sodium carbonate medium (Scheme 19 c) [ 58 ]. Scheme 19 a Synthesis of 11-aza-5 H -benzo[a]phenoxazin-5-one derivatives via condensation reaction [ 56 ]. b Synthetic route to pyrido[3,2-a]phenoxazine [ 57 ].…”
Section: Synthetic Methods To Prepare Several Phenoxazine Derivativesmentioning
confidence: 99%
“… a Synthesis of 11-aza-5 H -benzo[a]phenoxazin-5-one derivatives via condensation reaction [ 56 ]. b Synthetic route to pyrido[3,2-a]phenoxazine [ 57 ].…”
Section: Synthetic Methods To Prepare Several Phenoxazine Derivativesmentioning
Phenoxazines have sparked a lot of interest owing to their numerous applications in material science, organic light-emitting diodes, photoredox catalyst, dye-sensitized solar cells and chemotherapy. Among other things, they have antioxidant, antidiabetic, antimalarial, anti-alzheimer, antiviral, anti-inflammatory and antibiotic properties. Actinomycin D, which contains a phenoxazine moiety, functions both as an antibiotic and anticancer agent. Several research groups have worked on various structural modifications over the years in order to develop new phenoxazines with improved properties. Both phenothiazines and phenoxazines have gained prominence in medicine as pharmacological lead structures from their traditional uses as dyes and pigments. Organoelectronics and material sciences have recently found these compounds and their derivatives to be quite useful. Due to this, organic synthesis has been used in an unprecedented amount of exploratory alteration of the parent structures in an effort to create novel derivatives with enhanced biological and material capabilities. As a result, it is critical to conduct more frequent reviews of the work done in this area. Various stages of the synthetic transformation of phenoxazine scaffolds have been depicted in this article. This article aims to provide a state of the art review for the better understanding of the phenoxazine derivatives highlighting the progress and prospects of the same in medicinal and material applications.
Graphical abstract
“…Nan’ya et al reported the synthesis of 11-aza-5 H -benzo[a]phenoxazin-5-one derivatives, 59 by the condensation of 5-substituted-2,3-dihalogeno-1,4–naphthoquinone, 58 with 2-amino-3-hydroxypyridine, 55 in the presence of potassium acetate and in benzene/ethanol medium (Scheme 19 a) [ 56 ]. Ishii reported the acid-catalysed synthesis of pyrido[3,2-a]phenoxazine, 61 which was obtained by the condensation of 2-aminophenol and 4,6-dihydroxyquinoline-5,8-dione, 60 (Scheme 19 b) [ 57 ].…”
Section: Synthetic Methods To Prepare Several Phenoxazine Derivativesmentioning
confidence: 99%
“…Okafor et al reported the synthesis of another phenoxazine-containing compound, 6-chlorobenzo[a]-11-azaphenoxazine-5-one, 63 by refluxing 2,3-dichloro-1,4-naphthoquinone, 62 with 2-amino-3-pyridinol, 55 in chloroform and anhydrous sodium carbonate medium (Scheme 19 c) [ 58 ]. Scheme 19 a Synthesis of 11-aza-5 H -benzo[a]phenoxazin-5-one derivatives via condensation reaction [ 56 ]. b Synthetic route to pyrido[3,2-a]phenoxazine [ 57 ].…”
Section: Synthetic Methods To Prepare Several Phenoxazine Derivativesmentioning
confidence: 99%
“… a Synthesis of 11-aza-5 H -benzo[a]phenoxazin-5-one derivatives via condensation reaction [ 56 ]. b Synthetic route to pyrido[3,2-a]phenoxazine [ 57 ].…”
Section: Synthetic Methods To Prepare Several Phenoxazine Derivativesmentioning
Phenoxazines have sparked a lot of interest owing to their numerous applications in material science, organic light-emitting diodes, photoredox catalyst, dye-sensitized solar cells and chemotherapy. Among other things, they have antioxidant, antidiabetic, antimalarial, anti-alzheimer, antiviral, anti-inflammatory and antibiotic properties. Actinomycin D, which contains a phenoxazine moiety, functions both as an antibiotic and anticancer agent. Several research groups have worked on various structural modifications over the years in order to develop new phenoxazines with improved properties. Both phenothiazines and phenoxazines have gained prominence in medicine as pharmacological lead structures from their traditional uses as dyes and pigments. Organoelectronics and material sciences have recently found these compounds and their derivatives to be quite useful. Due to this, organic synthesis has been used in an unprecedented amount of exploratory alteration of the parent structures in an effort to create novel derivatives with enhanced biological and material capabilities. As a result, it is critical to conduct more frequent reviews of the work done in this area. Various stages of the synthetic transformation of phenoxazine scaffolds have been depicted in this article. This article aims to provide a state of the art review for the better understanding of the phenoxazine derivatives highlighting the progress and prospects of the same in medicinal and material applications.
Graphical abstract
“…Reports disclosed that phenoxazine derivatives are widely applied as organic light‐emitting diodes . The earliest modification of the structure of the parent compounds 1 and 2 in which benzene rings are fused to the sides of ring A and/or C results in nonlinear phenothiazine and phenoxazine rings of which benzo[a]phenothiazine and benzo[a]phenoxazine 3 and their derivatives were the most popular ones .…”
Chloro‐substituted phenothiazines and phenoxazines were successfully derivatized with phenylboronic and styrylboronic acids using Suzuki–Miyaura cross‐coupling reaction catalyzed by Pd(0)/XPhos for the first time in good yields. The protocol employed 4 mol% Pd and 7 mol% XPhos with K3PO4 in acetonitrile at 80°C. The reaction condition is compatible with carbonyl and unprotected N–H groups in substrates. Structural assignments were established by combined spectroscopic (UV, IR, 1H, and 13C NMR), MS, and elemental analytical data.
“…In con tin u a tion of our study for the syn the sis of heterocyclic ni tro gen dervatives, [1][2][3][4][5][6] we were in ter ested in the re action of arylnaphthoquinones with thioglycolic acid and primary ar o matic amines giv ing two types of the con den sa tion prod ucts. 6 The quin oxa line, 4,7-14 phenazine, [15][16][17][18] phenoxazine 15,19 and phe no thi azine, 20,21 ring sys tems have been ex ten sively stud ied and many such com pounds have now be come commer cially avail able and are widely used in med i cal practice 22,23 and in the dye in dus try. 24 This led us to syn the size some new re lated com pounds.…”
Cycloaddition reaction of 2‐aryl‐1,4‐benzoquinones 1a‐d with a number of different dienes, namely 2,3‐dimethylbutadiene; 1,4‐diphenylbutadiene and anthracene yield 2‐aryl‐6,7‐dimethyl‐1,4‐ naphthoquinones 3a,b; 2,5,8‐triphenyl‐1,4‐naphthoquinone 4 and 2‐aryl‐1,4,9,10‐tetrahydro‐9,10‐o‐benzoanthracene‐1,4‐dione 5, respectively were investigated. In addition, the cycloaddition reaction of 2‐aryl‐1,4‐benzoquinones 1d,e with 2,3‐dimethylbutadiene was also investigated to yield 2‐aryl‐5,8‐dihydro‐6,7‐dimethyl‐1,4‐naphthohydroquinones 2a,b. Cyclocondensation reactions of Diels‐Alder adducts 2b, 3b, 5a with ethylenediamine, o‐substituted primary aromatic amines gave quinoxaline, phenazine, phenoxazine and phenothiazine ocyclic derivatives 6–14.
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