2089-82-9Relevant academic research and scientific papers
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
Microwave-assisted Domino Cyclization for the Synthesis of Novel Spiro-benzo[a]phenazine Annulated Heterocycles Catalyzed by a Basic Ionic Liquid
Yazdani-Elah-Abadi, Afshin,Mohebat, Razieh,Kangani, Mehrnoush
, p. 690 - 698 (2017)
An efficient and green strategy for the improved synthesis of a biologically and pharmaceutically interesting multi-functionalized diverse novel spiro-benzo[a]phenazine annulated heterocycles was developed with the assistance of microwave irradiation. A sequential one-pot, two-step domino reaction starting from 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, a cyclic carbonyl compound, and 1,3-indandione in the presence of a basic ionic liquid (1-butyl-3-methylimidazolium hydroxide) as an expedient, ecofriendly and reusable catalyst afforded the corresponding novel spiro[benzo[a]indeno[2′,1′:5,6]pyrano[2,3-c]phenazine] derivatives with high yield under solvent-free conditions. This domino Knoevenagel–Michael annulation reaction provided five new bonds (two C–C, two C?N, and one C–O) and two new rings through multiple operations in a single flask.
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.
A rapid and efficient domino protocol for the synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline derivatives
Mohebat, Razieh,Yazdani Elah Abadi, Afshin,Maghsoodlou, Malek-Taher
, p. 6039 - 6048 (2016)
Benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline derivatives were synthesized via a one-pot, two-step procedure from a three-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, 1,2-diamines, and tetracyanoethylene in the presence of pyridine as an efficient catalyst. This novel procedure has the advantages of operational simplicity, short reaction times, easy work-up, avoiding costly syntheses, and the products do not require further purification, which provides an efficient and economical method for the synthesis of related products in excellent yields.
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 novel one-pot and rapid synthesis of polyfunctionalized benzo[a]pyrimido[5’,4’:5,6] pyrido[2,3-c]phenazine derivatives under microwave irradiation
Tabibian, Mahdieh,Mohebat, Razieh,Tabatabaee, Masoumeh
, p. 1008 - 1017 (2018)
A one-pot, environmentally friendly, and efficient protocol for the synthesis of novel polyfunctionalized benzo[a]pyrimido[5’,4’:5,6]pyrido[2,3-c]phenazine derivatives has been reported by a one-pot, four-component sequential reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, benzaldehydes, and 6-amino-1,3-dimethyluracil in the presence of p-TSA as a nontoxic, inexpensive, ecofriendly, and efficacious solid acid catalyst. Two C-C bonds, two C=N bonds, and one C-N bond, as well as two new rings, were formed in this reaction. Through this procedure, compounds with substantial biological and pharmaceutical properties are generated in a single operation. Factors such as high yields, less reaction time, operational simplicity, and lack of any dangerous reagents/solvents have made this process a green one.
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.
Theophylline as the catalyst for the diastereoselective synthesis of: Trans -1,2-dihydrobenzo [a] furo[2,3- c] phenazines in water
Yazdani-Elah-Abadi, Afshin,Mohebat, Razieh,Maghsoodlou, Malek-Taher
, p. 84326 - 84333 (2016)
An efficient, convenient and environmentally benign procedure for the synthesis of novel 1,2-dihydrobenzo[a]furo[2,3-c]phenazine derivatives with high diastereoselectivity has been developed by a domino four-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, aromatic aldehyde and pyridinium ylide in the presence of a catalytic amount of theophylline as an expedient, eco-friendly and reusable solid base catalyst in water. This one-pot process produces biologically and pharmacologically significant heterocycles with the formation of five new bonds (two C-C, two CN and one C-O) and two new rings in a single operation and this effective green process provides considerable advantages such as: operational simplicity, short reaction time, high yields, reusability of catalyst, absence of any tedious workup or purification and avoiding hazardous reagents/solvents.
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
Preparation and characterization of new inorganic–organic hybrid catalyst H3PMo12O40/Hyd-SBA-15 and its application in the domino multi-component reaction
Safaei-Ghomi, Javad,Bakhtiari, Atefeh
, (2019)
We present novel inorganic–organic hybrid catalyst to accomplish domino multi-component reaction (MCR) for synthesis of 3-amino-2′-oxospiro[benzo[c]pyrano[3,2-a]phenazine-1,3′-indoline]-2-carbonitrile/carboxylate derivatives. This methodology offers remarkable development by easy production of H3PMo12O40/Hyd-SBA-15 in regard to solving the problem of using harsh catalysts, also it demonstrates to be impressive and environmentally friendly in term of low reaction times and high yields.
