2089-82-9Relevant articles and documents
Two step, one-pot sequential synthesis of functionalized hybrid polyheterocyclic scaffolds: Via a solid state melt reaction (SSMR)
Bakthadoss, Manickam,Srinivasan, Jayakumar,Hussain, Mir Ashiq,Sharada, Duddu S.
, p. 24314 - 24318 (2019)
A new one pot assembly of highly functionalized benzo[a]phenazinone fused chromene/bicyclic scaffolds via a domino Knoevenagel intramolecular hetero-Diels-Alder (IMHDA) strategy using a solid state melt reaction (SSMR) of 2-hydroxynaphthalene 1,4-dione, o
Study on Synthesis and Fluorescence of Novel Benzofused Phenazine π-Conjugated Skeleton with Coumarin and Isophoron Cores
Choudhary, Amol S.,Patil, Sharad R.,Sekar, Nagaiyan
, p. 1095 - 1102 (2015)
The novel benzofused phenazine π-conjugated skeleton with a coumarin and isophoron core was synthesized, characterized, and condensed with suitably substituted active methylene compounds by classical Knoevenagel condensation reaction to obtain novel mono-styryl dyes 6a-6d. These novel styryl dyes have hue varying from yellow to violet. The geometries of the styryl dyes were optimized at B3LYP/6-31G (d) level of theory, and their electronic excitation properties were evaluated using density functional theory.
DABCO-catalyzed multi-component domino reactions for green and efficient synthesis of novel 3-oxo-3H-benzo[a]pyrano[2,3-c]phenazine-1-carboxylate and 3-(5-hydroxybenzo[a]phenazin-6-yl)acrylate derivatives in water
Mohebat, Razieh,Yazdani-Elah-Abadi, Afshin,Hazeri, Nourallah
, p. 943 - 948 (2017)
An efficient, convenient and environmentally benign procedure for the synthesis of novel 3-oxo-3H-benzo[a]pyrano[2,3-c]phenazine-1-carboxylate and 3-(5-hydroxybenzo[a]phenazin-6-yl)acrylate derivatives has been developed by domino three-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines and acetylenic esters in the presence of a catalytic amount of DABCO as an expedient, eco-friendly and reusable base catalyst in water. This green process produces biologically and pharmacologically significant heterocycles in a one-pot single operation and offers considerable advantages such as: operational simplicity, short reaction time, high yields, reusability of catalyst, absence of any tedious workup or purification and avoids hazardous reagents/solvents.
A rapid and simple diversity-oriented synthesis of novel 3-amino-2′-oxospiro [benzo[c]pyrano[3,2-a]phenazine-1,3′-indoline]- 2-carbonitrile/carboxylate derivatives via a one-pot, four-component domino reaction
Mahdavinia, Gholam Hossein,Mirzazadeh, Maryam,Notash, Behrouz
, p. 3487 - 3492 (2013)
An efficient regio- and chemoselective method for the synthesis of novel 3-amino-2′-oxospiro[benzo[c]pyrano[3,2-a]phenazine-1,3′-indoline] -2-carbonitrile/carboxylate derivatives has been developed via the one-pot, four-component domino coupling of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, isatins, and malononitrile/cyanoacetic ester in the presence of DABCO under reflux conditions in excellent yields. The merit of this cascade formation of two CN bonds/Knoevenagel condensation/Michael addition/cyclization sequence is highlighted by its high atom-economy, excellent yields, efficiency of producing five new bonds (two C-N, two C-C, and one C-O), and one stereocenter in a single operation.
Synthesis of a new library of pyrano-phenazine derivatives via a novel three-component protocol
Shaabani, Ahmad,Ghadari, Rahim,Arabieh, Masoud
, p. 228 - 236 (2014)
The pyrano-phenazine derivatives 6 were synthesized by an efficient procedure using the reaction between benzo[a]phenacin-5-ols with the condensation product of an aldehyde with Meldrum's acid in the presence of a catalytic amount of Et3N at ambient temperature. The procedure is very simple, and products could be separated from the reaction media by simple filtration. High functional-group tolerance both in the benzo[a]phenazin-5-ol and aldehyde moieties, facile reaction procedure, medium-to-high yields, and simple separation of the products from the reaction media are the advantages of this route. Copyright
PTSA-catalyzed four-component domino reactions for the one-pot synthesis of functionalized 11H-benzo[a]benzo[6,7]chromeno[2,3-c]phenazine-11,16(17H)-diones in PEG
Mohebat, Razieh,Yazdani Elah Abadi, Afshin,Maghsoodlou, Malek-Taher,Mohammadi, Mohsen
, p. 5915 - 5926 (2016)
An efficient p-toluenesulfonic acid catalyzed synthesis of 11H-benzo[a]benzo[6,7]chromeno[2,3-c]phenazine-11,16(17H)-dione derivatives has been described by one-pot, four-component condensation of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aromatic aldehydes using polyethylene glycol as solvent. This domino protocol produces biologically considerable heterocycles with the formation of C–C, C=C, C–N, C=N, C–O bonds in a single operation and this efficient green process provides significant advantages such as: operational simplicity, easy work-up procedure, high yields, avoidance of hazardous or toxic catalysts and organic solvents, and is devoid of inessential derivatization and generation of hazardous substances.
Novel 6-(1H-benzo[d]imidazol-2-yl) benzo[a]phenazin-5-ol Derivatives with Dual Emission and Large Stokes Shift Synthesis, Photophysical Properties and Computational Studies
Choudhary, Amol S.,Sekar, Nagaiyan
, p. 835 - 848 (2015)
Novel phenazine containing dyes were obtained by the condensation of 5-hydroxybenzo[a]phenazine-6-carbaldehyde and 5-chloro-benzo[a]phenazine-6-carbaldehyde with 1,2-diaminobenzene. The dyes were characterized by FT-IR, 1H NMR, elemental analysis and mass spectra. The UV-vis absorption and fluorescence emission spectra of the dyes were studied in solvents of differing polarity; the dyes exhibited excited state intra molecular proton transfer. The structural changes due to excited state intramolecular proton transfer (ESIPT) phenomenon in terms of bond angle, bond distances and geometry were investigated with the help of DFT computations. The computed absorption and emission were in agreement with the experimental absorption and emission.
Nanomagnetically modified thioglycolic acid (γ-Fe2O3@SiO2-SCH2CO2H): Efficient and reusable green catalyst for the one-pot domino synthesis of spiro[benzo[a]benzo[6,7]chromeno[2,3-c]phenazine] and benzo[a]benzo[6,7]chromeno[2,3-c]phenazines
Abbasi Pour, Sajjad,Yazdani-Elah-Abadi, Afshin,Afradi, Mojgan
, (2017)
Superparamagnetic nanoparticles of modified thioglycolic acid (γ-Fe2O3@SiO2-SCH2CO2H) represent a new, efficient and green catalyst for the one-pot synthesis of novel spiro[benzo[a]benzo[6,7]chromeno[2,3-c]phenazine] derivatives via domino Knoevenagel–Michael–cyclization reaction of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, ninhydrin and isatin. This novel magnetic organocatalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least six times without significant loss in its activity. The catalyst was fully characterized using various techniques. This procedure was also applied successfully for the synthesis of benzo[a]benzo[6,7]chromeno[2,3-c]phenazines.
An efficient catalyst-free synthesis of novel benzo[a][1,3]oxazino[6,5-c]phenazine derivatives via one pot four-component domino protocol in water
Khanna, Garima,Chaudhary, Ankita,Khurana, Jitender M.
, p. 6652 - 6654 (2014)
A catalyst-free multicomponent reaction (MCR) capable of affording a wide range of novel benzo[a][1,3]oxazino[6,5-c]phenazine derivatives via one pot two-step domino protocol, in water is reported. Catalyst-free conditions along with green solvent system
A green and efficient four-component sequential protocol for the synthesis of novel 16-(aryl)benzo[a]indeno[2′,1′:5,6]pyrano[2,3-c]phenazin-15(16H)-one derivatives using oxalic acid as a reusable and cost-effective organic catalyst
Mohebat, Razieh,Abadi, Afshin Yazdani Elah,Maghsoodlou, Malek-Taher,Mohammadi, Mohsen,Heydari, Reza
, p. 7121 - 7132 (2016)
A sequential one-pot four-component reaction for the efficient synthesis of novel 16-(aryl)benzo[a]indeno[2′,1′:5,6]pyrano[2,3-c]phenazin-15(16H)-one derivatives has been developed. The synthesis was achieved by reacting 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamine, aromatic aldehydes, and 1,3-indandione in the presence of oxalic acid as a reusable and homogenous organocatalyst in EtOH/H2O (1:1) under reflux. The present approach of this methodology offers several advantages such as high yields, clean reaction profiles, operational simplicity, simple work-up procedures, and green aspects by avoiding toxic catalysts and solvents.
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Ott
, p. 827,831,836 (1959)
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Indeno-furan based colorimetric and on-off fluorescent pH sensors
Aggarwal, Komal,Khurana, Jitender M.
, p. 23 - 29 (2015)
In this study, pH on-off fluorescent chemosensors based on indeno-furan derivatives have been designed, synthesized and characterized. The designed sensors were based on the change in structure of phenazine/ quinoxaline unit and keeping indeno-furan as common unit. These compounds exhibit pH dependent on/off fluorescence and thus act as fluorescent pH sensors. The change in fluorescence of 3a and 3b is reversible within the wide pH range of 2-11. The color change of these sensors could also be detected by naked eyes thus making them promising candidates as colorimetric pH indicators also.
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, Mohsen,Khanmoradi, Maryam,Mohammadi, Masoud
, (2020/02/05)
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 s
Zirconium@guanine@MCM-41 nanoparticles: An efficient heterogeneous mesoporous nanocatalyst for one-pot, multi-component tandem Knoevenagel condensation–Michael addition–cyclization Reactions
Nikoorazm, Mohsen,Mohammadi, Masoud,Khanmoradi, Maryam
, (2020/06/04)
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 a
