- One-pot, three-component synthesis of polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridine and benzo[g]pyrazolo[3,4-b]quinoline derivatives in the presence of silver nanoparticles (AgNPs)
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An efficient and straightforward protocol for one-pot, three-component reaction of aryl glyoxal monohydrates 1a-h, 5-amino-1-aryl-3-methylpyrazoles 2a,b and 4-hydroxyquinoline-2(1H)-one (3) or 2-hydroxy-1,4-naphthoquinone (4) using silver nanoparticles (AgNPs) as a high performance nanocatalyst in H2O/EtOH at 60°C afforded the corresponding polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridines 5a-h and benzo[g]pyrazolo[3,4-b]quinolines 6a-i, respectively. Excellent catalytic activity, high yields, employing green media and green nanocatalyst, cost-effective and simple procedure are some notable advantages of using AgNPs as a noble metal nanocatalyst in this synthetic strategy. The structures of fused heterocycles were confirmed by their Fourier transform infrared, proton nuclear magnetic resonance (1H-NMR), and 13C-NMR spectral data and microanalysis.
- Khalafy, Jabbar,Majidi Arlan, Fatemeh,Poursattar Marjani, Ahmad,Sarchami, Vahid
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p. 3961 - 3969
(2020/09/01)
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- Synthesis of Ethyl 2-Amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates by a One-pot, Three-Component Reaction in the Presence of TPAB
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In this research, in order to synthesize a series of ethyl 2-amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates, a green and an efficient method is proposed through one-pot three-component reaction of substituted arylglyoxals, ethyl cyanoacetate, and 4-hydroxyquinolin-2(1H)-one in the presence of terapropylammonium bromide as a catalyst in good yields. All synthesized new substances were characterized by FTIR, 1H-NMR, and 13C-NMR spectral data and elemental analysis.
- Poursattar Marjani, Ahmad,Khalafy, Jabbar,Farajollahi, Ayda
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p. 268 - 274
(2018/11/30)
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- A simple protocol for the green synthesis of a new series of pyrimido[4,5b][1,6]naphthyridines in the presence of silver nanoparticles (AgNPs)
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Eight polyfunctionalized pyrimidonaphthyridine derivatives has been synthesized, in 79-92% yields, via the one-pot, three-component reaction of aryl glyoxal monohydrates, 6-aminouracil and 4-hydroxyquinolin-2(1H)-one in H2O/EtOH in the presence of AgNPs under mild conditions. In this work colloidal AgNPs acts as an efficient, economical, green nanocatalyst, leading to a simple method of preparation.
- Marjani, Ahmad Poursattar,Khalafy, Jabbar,Arlan, Fatemeh Majidi,Eyni, Elham
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- Synthesis of 4-Hydroxy-3-(2-arylimidazo[1,2-a]pyridin-3-yl)quinolin-2(1H)-ones in the Presence of DABCO as an Efficient Organocatalyst
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The one-pot, three-component, synthesis of a new series of 4-hydroxy-3-(2-arylimidazo[1,2-a]pyridin-3-yl)quinolin-2(1H)-ones in the presence of DABCO as a catalyst has been achieved using aryl glyoxal monohydrates, quinoline-2,4(1H,3H)-dione, and 2-aminopyridine in H2O/EtOH under reflux conditions. The cheapness of organocatalyst, simple workup, operational simplicity, regioselectivity, and high yields are some advantages of this protocol.
- Khalafy, Jabbar,Etivand, Nasser,Poursattar Marjani, Ahmad,Khalillou, Neda
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p. 1857 - 1865
(2019/05/21)
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- One-pot, Three-component Synthesis of a New Series of 2-Amino-4-aroyl-5-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-carbonitrile in the Presence of SBA-15 as a Nanocatalyst
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One-pot, three-component reaction of arylglyoxals, malononitrile and 4-hydroxyquinolin-2(1H)-one in the presence of SBA-15 as a nanocatalyst and using green solvent systems under various temperatures afforded the 2-amino-4-aroyl-5-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-carbonitrile derivatives. The best yield (70-96%) were obtained using 20% mol of SBA-15 as a nanocatalyst in H2O/EtOH (1:1) at 80 °C. The simplicity of work up procedure, using green solvent system, and good to excellent yields of products are the main advantages of this synthetic strategy.
- Khalafy, Jabbar,Arlan, Fatemeh Majidi,Chalanchi, Shahin Soleimani
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p. 149 - 153
(2018/01/26)
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- A new synthesis of pyrrolo[3,2-d]pyrimidine derivatives by a one-pot, three-component reaction in the presence of L-proline as an organocatalyst
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A one-pot, three-component reaction of 4-hydroxycoumarin, arylglyoxals, and 6-aminouracil or 1,3-dimethyl-6-aminouracil in the presence of L-proline as an organocatalyst in acetic acid under reflux conditions provided a series of new pyrrolo[3,2-d]pyrimidine derivatives in good yields.
- Javahershenas, Ramin,Khalafy, Jabbar
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- A Green, Organometallic Catalyzed Synthesis of a Series of Novel Functionalized 4-Aroyl-4H-benzo[g]chromenes through One-pot, Three Component Reaction
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A new series of 4-aroyl-4H-benzo[g]chromene derivatives have been synthesized through an efficient, straightforward, and environmentally acceptable one-pot, three component reaction of malononitrile, different arylglyoxals, and 2-hydroxy-1,4-naphtoquinone (lawsone) in short reaction times and high to excellent yields. The zinc complex of amino acid L-proline, that is, Zn[L-proline]2 has been prepared and used as highly active, recyclable, noncorrosive, and water soluble Lewis acid catalyst for this transformation.
- Khalafy, Jabbar,Ilkhanizadeh, Siamand,Ranjbar, Masoumeh
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p. 951 - 956
(2018/02/15)
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- An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water
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An improved synthesis of 2-ethyl-5-(2-hydroxy-4-oxoquinolin-3(4H)-ylidene)-6-aryl-5,6-dihydroimidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxide derivatives 4a-k via the reaction of aryl glyoxal monohydrates 1a-k, quinoline-2,4-diol 2 and 2-amino-[1,3,4]thiadiazole (3) in the presence of Et3N/sulfamic acid in H2O is described. This green protocol is characterized by the use of the readily available catalyst and reactants, short reaction times, operational simplicity and high yields of products. The structures of all compounds were characterized by 1H NMR, 13C NMR and Fourier-transform infrared (FT-IR) spectral data and microanalyses.
- Khalafy, Jabbar,Etivand, Nasser,Khalillou, Neda
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p. 297 - 302
(2018/12/04)
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- Novel and convenient one-pot strategy for regioselective synthesis of new 5-aryl-3-methyl-1-phenyl-1,2-dihydro-7aH-pyrazolo[3,4-c]pyridazin-7a-ol derivatives
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Abstract: We describe a novel and simple regioselective synthesis of 5-aryl-3-methyl-1-phenyl-1,2-dihydro-7aH-pyrazolo[3,4-c]pyridazin-7a-ol derivatives via one-pot three-component reaction of arylglyoxalmonohydrates, 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and hydrazine hydrate in presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) as base-organocatalyst at room temperature in acetonitrile. This one-pot method has the advantages of simple methodology, high atom economy, cost-effectiveness, high regioselectivity, and easy workup. Graphical Abstract: [Figure not available: see fulltext.].
- Rimaz, Mehdi,Mousavi, Hossein,Nikpey, Laya,Khalili, Behzad
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p. 3925 - 3937
(2017/06/20)
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- The catalyst-free syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by one-pot, three-component reactions
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Herein we report the syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by cyclocondensation of 1,3-diketones, 3-methyl-1-phenyl-1H-pyrazole-5-amine and arylglyoxals, under catalyst-free conditions in H2O/EtOH at reflux in 65–98% and 73–96% yields respectively. This protocol provides mild reaction conditions, good to high yields, non-catalytic, simple procedures and easy isolation of products to structurally diverse tricyclic pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives, which may have biological and pharmacological activities.
- Ezzati, Mahnaz,Khalafy, Jabbar,Marjani, Ahmad Poursattar,Prager, Rolf H.
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p. 6587 - 6596
(2017/10/23)
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- A Green Synthesis of 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile Derivatives by a One-pot Three-component Reaction
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The synthesis of polyfunctionalized 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile derivatives by a green approach was achieved via one-pot three-component reaction of arylglyoxals, malononitrile, and 1,3-dimethyl-6-aminouracil in the presence of urea as organocatalyst in EtOH:H2O (1:1) at 60°C. This protocol provides a mild and fast procedure to structurally diverse bicyclic pyridopyrimidines in good to excellent yields.
- Javahershenas, Ramin,Khalafy, Jabbar
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p. 3163 - 3168
(2017/10/06)
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- A Green and Convenient Route for the Regioselective Synthesis of New Substituted 3-Aryl-5H-indeno[1,2-c]pyridazines as Potential Monoamine Oxidase Type A Inhibitors
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Several indeno[1,2-c]pyridazines were efficiently synthesised using the one-pot, three-component reaction of substituted indanones, arylglyoxalmonohydrates, and hydrazine in the presence of 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) in water at room temperature. These substituted 3-aryl indeno[1,2-c]pyridazines can be considered as potential monoamine oxidase type A (MAOA) inhibitors. The advantages of this new strategy are the novelty of the indenopyridazine derivatives, high regioselectivity, use of water as the solvent, no requirement for toxic metal catalysts, and good to excellent yields.
- Rimaz, Mehdi,Aali, Farkhondeh,Khalili, Behzad,Prager, Rolf H.
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p. 660 - 668
(2017/05/31)
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- Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
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A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of "green chemistry". Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
- Karpov, Sergey V.,Grigor'Ev, Arthur A.,Kayukov, Yakov S.,Karpova, Irina V.,Nasakin, Oleg E.,Tafeenko, Victor A.
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p. 6402 - 6408
(2016/08/16)
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- Regiospecific one-pot, combinatorial synthesis of new substituted pyrimido[4,5-c]pyridazines as potential monoamine oxidase inhibitors
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New 3-aryl-6-methylpyrimido[4,5-c]pyridazine-5,7(6H ,8H)-diones and 3-aryl-6-ethyl-7-thioxo-7,8-dihydropyrimido[4,5- c]pyridazin-5(6H)-ones were efficiently synthesized via a regiospecific one-pot reaction of N -methylbarbituric acid and N -ethyl-2-thiobarbituric acid with various arylglyoxal monohydrates in the presence of hydrazine dihydrochloride in ethanol at 50°C. The target compounds were obtained in high yields and were regioisomerically pure after recrystallization. These new heterocycles may act as potential MAOB inhibitors.
- Rimaz, Mehdi,Pourhossein, Paria,Khalili, Behzad
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p. 244 - 254
(2015/05/27)
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- Two efficient one-pot approaches for regioselective synthesis of new 3-arylpyridazino[4,3-c]quinolin-5(6H)-ones
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Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.
- Rimaz, Mehdi
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p. 1529 - 1534
(2015/10/20)
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- Nucleophilic addition of (difluoromethyl)trimethylsilane to selected α-imino ketones and aryl diketones
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Abstract Chemoselective addition of (difluoromethyl)trimethylsilane (CHF2SiMe3) to the carbonyl bond of aryl glyoxal derived α-imino ketones, and selected diaryl 1,2-diketones were studied in the presence of initiators, such as potas
- Obijalska, Emilia,Utecht, Greta,Kowalski, Marcin K.,Mlostoń, Grzegorz,Rachwalski, Micha?
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p. 4701 - 4703
(2015/07/28)
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- Chemoselective trifluoromethylation of the C=N group of α-iminoketones derived from arylglyoxals
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Chemoselective addition of (trifluoromethyl)trimethylsilane to the CN group of N-(tert-butyl)-α-iminoketones in the presence of a fluoride ion as a catalyst was achieved under acidic conditions. Subsequent diastereoselective reductions of the obtained α-a
- Obijalska, Emilia,Kowalski, Marcin K.,Mlostoń, Grzegorz,Linden, Anthony,Heimgartner, Heinz
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p. 151 - 157
(2015/03/05)
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- Synthesis of α-ketothioamides via willgerodt-kindler reaction of arylglyoxals with amines and sulfur under solvent-free conditions
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Willgerodt-Kindler reaction of arylglyoxal hydrates with secondary amines and elemental sulfur under solvent-free conditions at 80 °C is developed, in which α-ketothioamides are obtained in 70-90% yield in 0.6-1 hour. The X-ray crystal-structure analysis for one compound was obtained. Georg Thieme Verlag Stuttgart . New York.
- Eftekhari-Sis, Bagher,Khajeh, Saleh Vahdati,Büyükgüng?r, Orhan
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p. 977 - 980
(2013/06/27)
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- Willgerodt-Kindler reaction of arylglyoxals with amines and sulfur in aqueous media: A simple and efficient synthesis of -ketothioamides
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A simple and efficient method for the synthesis of -ketothioamides via the Willgerodt-Kindler reaction is developed. Reactions were carried out between arylglyoxal hydrates, amines and elemental sulfur in water at 80°C to afford corresponding -ketothioamides in good to high yields in a short reaction time.
- Eftekhari-Sis, Bagher,Vahdati-Khajeh, Saleh,Amini, S. Motahhareh,Zirak, Maryam,Saraei, Mahnaz
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p. 464 - 473
(2013/10/21)
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- A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis
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An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.
- Wang, Pan,Tao, Wen-Jie,Sun, Xiu-Li,Liao, Saihu,Tang, Yong
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supporting information
p. 16849 - 16852
(2013/12/04)
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- A convenient synthesis of novel 2,8-disubstituted pyrido[3,4-b]pyrazines possessing biological activity
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A regioselective synthetic route to 2,8-disubstituted pyrido[3,4-b] pyrazines, by initial condensation reaction between suitable diaminopyridines and α-keto aldehydes equivalents, has been developed. Focusing on the functionalization on C-8, 2-aryl-8-bromo- and 8-amino-2-arylpyrido[3,4-b] pyrazines have been synthesized. Anilines, amides, and ureas have been introduced at the 8-position from key intermediates. 2,8-Disubstituted pyrido[3,4-b]pyrazines thus prepared were found to be of biological interest. Georg Thieme Verlag Stuttgart. New York.
- Antoine, Maud,Gerlach, Matthias,Guenther, Eckhard,Schuster, Tilmann,Czech, Michael,Seipelt, Irene,Marchand, Pascal
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experimental part
p. 69 - 82
(2012/03/27)
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- The Photochemistry of the Host-Guest Complex. VII. The Photoreaction of Dicyanopyrazine Derivatives Having a Crown Ether Moiety
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The irradiation of 4'-(5,6-dicyano-2-pyrazinyl)benzo-15-crown-5 and 5,6-dicyano-2-(3,4-dimethoxyphenyl)pyrazine in the presence of a tertiary or secondary amine caused reductive decyanation to give 5-decyano derivatives, which in turn gave bis(decyano) derivatives on further irradiation.Free-energy changes upon single-electron transfer from the amine to the excited state of dicyanopyrazine derivatives are exothermic for triethylamine and diethylamine, but endothermic for butylamine.The single-electron transfer was evidenced by the effect of the sodium ion on the quantum yields of the reaction products and the fluorescence quenching.
- Tada, Masaru,Hamazaki, Hirohide,Hirano, Hideki
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p. 3865 - 3869
(2007/10/02)
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