- 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)
-
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
-
p. 3961 - 3969
(2020/09/01)
-
- Series of Functionalized 5-(2-Arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1 H,3 H)-diones: A Water-Mediated Three-Component Catalyst-Free Protocol Revisited
-
A water-mediated and catalyst-free practical method for the synthesis of a new series of pharmaceutically interesting functionalized 5-(2-arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1H,3H)-diones has been accomplished based on a one-pot multicomponent reaction between arylglyoxal monohydrates, 2-aminopyridines/2-aminopyrimidine, and barbituric/N,N-dimethylbarbituric acids under reflux conditions. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use of water as reaction medium, clean reaction profiles, operational simplicity, ease of product isolation/purification without the aid of tedious column chromatography, good to excellent yields, and high atom-economy and low E-factor.
- Brahmachari, Goutam,Nayek, Nayana,Karmakar, Indrajit,Nurjamal, Khondekar,Chandra, Swapan K.,Bhowmick, Anindita
-
p. 8405 - 8414
(2020/07/16)
-
- 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)
-
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
-
-
- 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
-
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
-
p. 1857 - 1865
(2019/05/21)
-
- A Facile and Effective Procedure for Synthesis of Polyfunctionalized Bis (imidazolyl) Pyrrole/Imidazolyl Indole from Pyrrole/Indole with Arylglyoxals and N-aryl amidines
-
Heterocyclic systems containing bis (imidazolyl) pyrrole or imidazolyl indole moieties were synthesized by heterocyclization of pyrrole or indole with arylglyoxal monohydrates and N-aryl amidines in ethanol catalyzed by FeCl3 at room temperature. The paper reports a facile, efficient, and environmentally friendly protocol for the synthesis of new products. Products were isolated by simple filtration, and their structures were established from their spectroscopic data.
- Masoudi, Mozhgan,Shahbazi-Manshadi, Mohammad Reza,Anary-Abbasinejad, Mohammad
-
p. 2772 - 2778
(2019/11/03)
-
- One-pot three-component synthesis of a series of 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in the presence of aluminum oxide as a nanocatalyst
-
[Figure not available: see fulltext.] One-pot three-component reaction of arylglyoxals, 3-aryl-3-oxopropanenitriles, and 5-amino-1-aryl-3-methylpyrazoles using various solvent systems and different catalysts under reflux conditions afforded the corresponding 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]- pyridine-5-carbonitrile derivatives. The best yields (70–91%) were obtained using Al2O3 as a nanocatalyst in H2O–EtOH, 1:1, under reflux conditions. The simplicity of workup procedure, the novelty of pyrazolopyridines, green solvent system, easy preparation of a nanocatalyst, and good to excellent yields of the products are the advantages of this synthetic strategy. The structures of all products were confirmed by FT-IR, 1H and13C NMR, and mass spectral data.
- Arlan, Fatemeh Majidi,Khalafy, Jabbar,Maleki, Ramin
-
-
- 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
-
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
-
p. 149 - 153
(2018/01/26)
-
- 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
-
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
-
-
- A Green, Organometallic Catalyzed Synthesis of a Series of Novel Functionalized 4-Aroyl-4H-benzo[g]chromenes through One-pot, Three Component Reaction
-
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
-
p. 951 - 956
(2018/02/15)
-
- Synthesis of new indolylpyrrole derivatives via a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in aqueous media
-
A novel synthesis of indolylpyrrole derivatives is described by a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in water as solvent at 60 °C without using any catalyst or promoter. The FT-IR, 1H NMR, 13C NMR spectral and elemental analysis confirm the structures of the products.
- Mousavizadeh, Fereshteh,Talebizadeh, Mahdiyeh,Anary-Abbasinejad, Mohammad
-
supporting information
p. 2970 - 2974
(2018/06/30)
-
- Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones
-
A highly regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates to afford N-1 and C-2 indolyl diketones in moderate to good yields is described. Notably, the control of regioselectivity is achieved by small changes in the Cu catalyst, additive and solvent. Importantly, the intermediates for N-1 and C-2 diacylation were detected and two plausible pathways were also proposed.
- Pan, Dalong,Chu, Jinpeng,Gao, Xianrui,Wang, Cuiping,Meng, Qingtao,Chi, Haijun,Dong, Yan,Duan, Chunying,Zhang, Zhiqiang
-
supporting information
p. 6998 - 7003
(2018/10/17)
-
- An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water
-
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
-
p. 297 - 302
(2018/12/04)
-
- 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
-
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.
-
p. 6587 - 6596
(2017/10/23)
-
- Catalytic asymmetric Meerwein-Ponndorf-Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)3 complex
-
An asymmetric Meerwein-Ponndorf-Verley (MPV) reduction of glyoxylates was for the first time accomplished via an N,N′-dioxide/Y(OTf)3 complex with aluminium alkoxide and molecular sieves (MSs) as crucial additives. A variety of optically active α-hydroxyesters were obtained with excellent results. A possible reaction mechanism was proposed based on the experiments.
- Wu, Wangbin,Zou, Sijia,Lin, Lili,Ji, Jie,Zhang, Yuheng,Ma, Baiwei,Liu, Xiaohua,Feng, Xiaoming
-
supporting information
p. 3232 - 3235
(2017/03/20)
-
- Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells
-
2,2-Dihydroxyarylethanones, readily prepared from the commercially available aromatic ethyl ketones, were reacted with resorcinol, 3-methoxyphenol or 2-methoxyphenol in multi steps one-pot manner promoted by trifluoroacetic acid to furnish the 2,3-diarylbenzofuran derivatives in 22–95% yield. Sixteen targeted compounds were synthesized and characterized by 1H NMR, 13C NMR and HRMS. MTT assay indicated that most compounds possessed effectively inhibitory activities against the proliferation of HeLa cell. Among them, 4f had the highest inhibitory activities, with the IC50 being 13.40?±?2.04?μmol/L. Cell cycle analysis, Annexin V-FITC/propidium iodide dual staining assay and western blotting analysis revealed that 4f inhibited the proliferation of Hela cell through apoptosis induction in a dose-dependent manner via obviously up-regulated the levels of Bak and Bim, while striking down-regulated the level of Bcl-2 and Bcl-xL protein.
- He, Guo-Xue,Yuan, Jing-Mei,Zhu, Hai-Miao,Wei, Kai,Wang, Ling-Yun,Kong, Shi-Lin,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa
-
supporting information
p. 1660 - 1664
(2017/04/04)
-
- Naphthol synthesis: Annulation of nitrones with alkynes: Via rhodium(III)-catalyzed C-H activation
-
An efficient and redox-neutral naphthol synthesis has been realized via rhodium(iii) catalyzed C-H activation of α-carbonyl nitrones and annulation with alkynes, where the nitrone group functioned as a traceless directing group.
- Wang, Qiang,Xu, Youwei,Yang, Xifa,Li, Yunyun,Li, Xingwei
-
supporting information
p. 9640 - 9643
(2017/09/01)
-
- 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
-
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
-
p. 3163 - 3168
(2017/10/06)
-
- 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
-
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
-
p. 3925 - 3937
(2017/06/20)
-
- 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
-
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.
-
p. 660 - 668
(2017/05/31)
-
- Keto-Enol Thermodynamics of Breslow Intermediates
-
Breslow intermediates, first postulated in 1958, are pivotal intermediates in carbene-catalyzed umpolung. Attempts to isolate and characterize these fleeting amino enol species first met with success in 2012 when we found that saturated bis-Dipp/Mes imida
- Paul, Mathias,Breugst, Martin,Neud?rfl, J?rg-Martin,Sunoj, Raghavan B.,Berkessel, Albrecht
-
supporting information
p. 5044 - 5051
(2016/05/19)
-
- Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
-
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.
-
p. 6402 - 6408
(2016/08/16)
-
- Nucleophilic addition of (difluoromethyl)trimethylsilane to selected α-imino ketones and aryl diketones
-
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?
-
p. 4701 - 4703
(2015/07/28)
-
- Regiospecific one-pot, combinatorial synthesis of new substituted pyrimido[4,5-c]pyridazines as potential monoamine oxidase inhibitors
-
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
-
p. 244 - 254
(2015/05/27)
-
- Synthesis of biologically important, fluorescence active 5-hydroxy benzo[g]indoles through four-component domino condensations and their fluorescence "Turn-off" sensing of Fe(iii) ions
-
Several highly substituted 2-pyrrolyl-2-cyanoacetamides were prepared through four-component domino condensation of various easily available 1,3-dicarbonyl compounds, amines, arylglyoxals and malononitrile. Subsequently these cyanoacetamide derivatives were converted into biologically important 5-hydroxy benzo[g]indoles through thermal cyclization under metal-free conditions. The synthesized 5-hydroxy benzo[g]indoles are fluorescence active with good quantum yields (ΦF = ~0.50). They also show excellent fluorescence "Turn-off" sensing of Fe3+ ions (detection limit = ~1.2 × 10-6 M). The interaction of 5-hydroxy benzo[g]indoles with Fe3+ ions can also be monitored through UV-Vis spectral change and naked-eye colour change in the presence and absence of UV radiation. The 1H NMR titration unambiguously proves the formation of a complex between 5-hydroxy benzo[g]indoles and Fe3+ ion through the coordination of -OH groups with the metal. The binding constant of the complex (metal : ligand = 1 : 1) has been measured using Benesi-Hildebrand equation and found to be ~7.97 × 103 M-1.
- Maity, Subhendu,Kundu, Ashis,Pramanik, Animesh
-
p. 52852 - 52865
(2015/06/25)
-
- Synthesis of 7-hydroxy-6,7-dihydro-indole and 6′,7′-dihydro-3,7′-biindole derivatives from domino reactions of arylglyoxals or methyl ketones with enamines
-
A series of interesting 7-hydroxy-2-aryl-6,7-dihydro-indol-4(5H)-ones 3 was successfully synthesized in moderate to good yields by the domino reactions of different arylglyoxals 1 with enamines 2 under catalyst-free conditions. 7-Hydroxy-2-aryl-6,7-dihydro-indol-4(5H)-ones 3 could also be prepared in moderate yields by the iodine-promoted one pot-two step reactions of methyl ketones 6 with enamines 2. The reaction of 3a with N-methyl indole 7a in the presence of PTSA afforded 2′-aryl-6′,7′-dihydro-[3,7′-biindol]-4′(5′H)-ones 8a in 81% yield. In addition, 3,7′-bis-indoles 8 could also be observed in 47-73% yields by one pot domino reaction of arylglyoxals 1 with enamines 2 and indoles 7 over two steps. This protocol provides a simple and practical method to construct diverse 7-hydroxy-6,7-dihydro-indole derivatives 3 and 3,7′-bis-indoles 8 from easily obtained starting materials.
- Lu, Xin-Mou,Cai, Zhong-Jian,Li, Jian,Wang, Shun-Yi,Ji, Shun-Jun
-
p. 51501 - 51507
(2015/06/25)
-
- Molybdate sulfuric acid-catalyzed one-pot synthesis of substituted coumarins under solvent-free conditions
-
An efficient method for the synthesis of new aryloylamido coumarins via a one-pot, three-component reaction of an aryl glyoxal, benzamide, and a 4-hydroxycoumarin in the presence of molybdate sulfuric acid under solvent-free conditions is reported. This h
- Khodabakhshi, Saeed,Karami, Bahador,Eskandari, Khalil
-
p. 7263 - 7272
(2015/09/29)
-
- Two efficient one-pot approaches for regioselective synthesis of new 3-arylpyridazino[4,3-c]quinolin-5(6H)-ones
-
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
-
p. 1529 - 1534
(2015/10/20)
-
- Chemoselective trifluoromethylation of the C=N group of α-iminoketones derived from arylglyoxals
-
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
-
p. 151 - 157
(2015/03/05)
-
- Na2S-mediated thionation: An efficient access to secondary and tertiary α-ketothioamides via Willgerodt-Kindler reaction of readily available arylglyoxals with amines
-
The task of this paper is to provide an efficient process for synthesis of secondary and tertiary α-ketothioamides via Willgerodt-Kindler reaction of readily available arylglyoxals with amines using Na2S as an effective catalyst. A plausible role for Na2S in the reaction of arylglyoxals with primary amines is proposed.
- Saeidian, Hamid,Vahdati-Khajehi, Saleh,Bazghosha, Homeira,Mirjafary, Zohreh
-
p. 700 - 710
(2015/10/19)
-
- Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
-
An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.
- Gao, Qing-He,Fei, Zhuan,Zhu, Yan-Ping,Lian, Mi,Jia, Feng-Cheng,Liu, Mei-Cai,She, Neng-Fang,Wu, An-Xin
-
-
- Synthesis of α-ketothioamides via willgerodt-kindler reaction of arylglyoxals with amines and sulfur under solvent-free conditions
-
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
-
p. 977 - 980
(2013/06/27)
-
- Regiospecific synthesis of novel furo[4,5- c ]coumarins in a one-pot reaction
-
A new and expedient assembly of an interesting class of amido-substituted furo[4,5-c]coumarins has been successfully achieved through a one-pot sequential coupling and cyclization strategy starting from 4-hydroxycoumarin, aryl glyoxals and benz-amide. All
- Karami, Bahador,Khodabakhshi, Saeed,Eskandari, Khalil
-
p. 998 - 1000
(2013/06/27)
-
- Willgerodt-Kindler reaction of arylglyoxals with amines and sulfur in aqueous media: A simple and efficient synthesis of -ketothioamides
-
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
-
p. 464 - 473
(2013/10/21)
-
- A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis
-
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
-
supporting information
p. 16849 - 16852
(2013/12/04)
-
- One-pot synthesis of benzamidonaphtho[2,1-b]furans and benzamidobenzo[b] furans as novel polycyclic heteroaromatic compounds
-
An operationally simple, green and efficient procedure for one-pot synthesis of novel polycyclic heteroaromatic compounds such as benzamidonaphtho[2,1-b]furans and benzamidobenzo[b]furans has been developed from the reaction of arylglyoxals, benzamide, and phenols. The reactions were mediated with low amounts of yttrium nitrate hexahydrate as a suitable Lewis acid catalyst without using solvent.
- Vahabinia, Hamid Reza,Karami, Bahador,Khodabakhshi, Saeed
-
p. 1323 - 1327
(2014/04/17)
-
- A convenient synthesis of novel 2,8-disubstituted pyrido[3,4-b]pyrazines possessing biological activity
-
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
-
-
- Microwave-assisted selenium dioxide oxidation of aryl methyl ketones to aryl glyoxals
-
We report an improved procedure for the synthesis of phenyl glyoxal and a series of para-substituted aryl glyoxals by microwave-assisted selenium dioxide oxidation. The reaction time has been reduced from several hours to three minutes for activated aryl methyl ketone substrates and 18 min for deactivated substrates, with all reactions affording quantitative conversion into the corresponding aryl glyoxals.
- Young, Ryan M.,Davies-Coleman, Michael T.
-
experimental part
p. 4036 - 4038
(2011/08/09)
-
- Asymmetric synthesis of β-amino alcohols by the transfer hydrogenation of α-keto imines
-
The asymmetric transfer hydrogenation of representative aryl and benzofuranyl 2-tert-butylaminoethanones with formic acid-triethylamine, catalyzed by RhCl[(R,R)-TsDPEN](C5Me5), produced the corresponding β-tert-butylamino alcohols in 97-99% ee. A short asymmetric synthesis of (R)-bufuralol, a potent β-adrenergic receptor antagonist, is described. This approach to β-amino alcohols from ketones circumvents the halogenation-reduction-amination sequence.
- Tafelska-Kaczmarek, Agnieszka,Prewysz-Kwinto, Andrzej,Skowerski, Krzysztof,Pietrasiak, Katarzyna,Kozakiewicz, Anna,Zaidlewicz, Marek
-
scheme or table
p. 2244 - 2248
(2010/11/03)
-
- Reactions of α-imino ketones derived from arylglyoxals with (trifluoromethyl)trimethylsilane; A new route to β-amino-α- trifluoromethyl alcohols
-
The reactions of α-imino ketones, derived from arylglyoxals, with (trifluoromethyl)trimethylsilane (CF3SiMe3) in DME solution, in the presence of catalytic amount of CsF, at room temperature, yield O-silylated β-imino alcohols in the
- Mloston, Grzegorz,Obijalska, Emilia,Tafelska-Kaczmarek, Agnieszka,Zaidlewicz, Marek
-
scheme or table
p. 1289 - 1296
(2011/02/22)
-
- The Oxidation of 6- and 7-Aryl-4(3H)-pteridinones by Immobilized Arthrobacter M-4 Cells Containing Xanthine Oxidase
-
The preparation of 6- and 7-(pX-phenyl)-4(3H)-pteridinones (X = H, CH3, OCH3) is described.The oxidation of these compounds by (immobilized) Arthrobacter M-4 cells containing xanthine oxidase has been studied.The oxidation monitored by uv spectroscopy usually goes fast, except for 7-(pX-phenyl)-4(3H)-pteridinones (X = CH3, OCH3), which are slowly oxidized.With bacterial cells immobilized in gelatine crosslinked with glutaraldehyde small laboratory-scale oxidations were carried out.Based on spectral data the products of the oxidation reactions are 6- and 7-aryllumazines.
- Meester, Johan W. G. De,Plas, Henk C. van der,Middelhoven, Wouter J.
-
p. 441 - 451
(2007/10/02)
-
- The Oxidation of Acetophenones to Arylglyoxals with Aqueous Hydrobromic Acid in Dimethyl Sulfoxide
-
The reaction of acetophenones with aqueous hydrobromic acid (HBr) in dimethyl sulfoxide (Me2SO) leads to the formation of arylglyoxals in good yield.Evidence has been obtained which suggests that this oxidation is mediated by a low concentration of molecular bromine, with the consecutive intermediacy of the α-bromo- and α-hydroxyacetophenones.The reaction of α-bromoacetophenone 2 with Me2SO alone provides the arylglyoxal 4 with the glyoxylic acid 6 as the major products.The α-hydroxyacetophenone 3 and thiol ester 5 are intermediates leading to 4 and 6, respectively, and may be isolated as minor products.The presence of water in the medium suppresses the formation of 5 and 6 and results in a cleaner conversion to 4.Treatment of aryl aldehyde 13 with 14 followed by reaction of the resulting 15 with aqueous HBr in Me2SO gave arylglyoxal 4 in good yield.
- Floyd, M. Brawner,Du, Mila T.,Fabio, Paul F.,Jacob, Linda A.,Johnson, Bernard D.
-
p. 5022 - 5027
(2007/10/02)
-