- A Facile and Effective Procedure for Synthesis of Polyfunctionalized Bis (imidazolyl) Pyrrole/Imidazolyl Indole from Pyrrole/Indole with Arylglyoxals and N-aryl amidines
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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
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- 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
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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
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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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- 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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- 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
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[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
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- 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
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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
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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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- 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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- The synthesis and ring opening of 3-aroyl(heteroaroyl)-1,2-dicyanocyclopropane-1,2-dicarboxylates
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3-Aroyl-1,1,2,2-tetracyanocyclopropanes undergo ring opening under the action of acetates, carbonates and hydroxides of alkali metals, resulting in the formation of stable 2-aroyl-1,1,3,3-tetracyanopropenide salts, which are of interest as potential co-ligands in the coordination polymers and as ionic liquid components. A method for producing new electron-deficient cyclopropanes, dimethyl 3-aroyl(heteroaroyl)-1,2-dicyanocyclopropane-1,2-dicarboxylates and their reactions with potassium acetate leading to the formation of the corresponding propenides is described.
- Karpov, Sergey V.,Kayukov, Yakov S.,Grigor'Ev, Arthur A.,Tafeenko, Victor A.
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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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- 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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- Molybdate sulfuric acid-catalyzed one-pot synthesis of substituted coumarins under solvent-free conditions
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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
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- I2-promoted tandem cyclization to synthesize polysubstituted pyrano[3,2-c]chromene-2,5-diones
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An efficient and convenient method for the synthesis of various substituted pyrano[3,2-c]chromene-2,5-diones was developed via the I2-promoted tandem cyclization of commercially available aryl methyl ketones and 4-hydroxycoumarins. Preliminary
- Cai, Qun,Zhuang, Shiyi,Yang, Mian,Peng, Na,Liu, Yi,Wu, Anxin
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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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- Synthesis of new indolylpyrrole derivatives via a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in aqueous media
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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
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- One-pot synthesis of benzamidonaphtho[2,1-b]furans and benzamidobenzo[b] furans as novel polycyclic heteroaromatic compounds
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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
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- A direct phosphine-mediated synthesis of polyfunctionalized pyrroles from arylglyoxals and β-enaminones
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An efficient one-pot reaction for the synthesis of pyrroles from β-enaminones and arylglyoxals is reported. This reaction, which is mediated by triphenylphosphine, eliminates triphenylphosphine oxide resulting in aromatization and has been employed to access a broad range of pyrrole derivatives.
- Masoudi, Mozhgan,Anary-Abbasinejad, Mohammad
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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 7-hydroxy-6,7-dihydro-indole and 6′,7′-dihydro-3,7′-biindole derivatives from domino reactions of arylglyoxals or methyl ketones with enamines
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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
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- A facile and effective procedure for synthesis of polyfunctionalized pyrrolines from simultaneously stirring of carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls
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An efficient one-pot synthesis of 2H-pyrroline derivatives by a four-component reaction between carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls in acetonitrile at room temperature under mild reaction conditions is reported. The addition rea
- Masoudi, Mozhgan,Anary-Abbasinejad, Mohammad,Maleki, Alireza
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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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- Copper-catalyzed selective oxidation of hydrazones through C(sp3)-H functionalization
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A simple and mild protocol for copper-catalyzed oxidation of hydrazones at the α-position has been reported. Various substrates are compatible, providing the corresponding products in moderate to good yields. This strategy provides an efficient and convenient solution for the synthesis of carbonyl hydrazone. A free radical pathway mechanism is suggested for the transformation.
- Jiang, Xiaoying,Shen, Jiabin,Wu, Haifeng,Xu, Jun,Zhang, Pengfei,Zhu, Qing
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p. 8917 - 8923
(2021/11/04)
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- Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1 H-benzo[ d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage
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An unprecedented I2/FeCl3-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated N-heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp3)-H amination/C-N bond cleavage were key reaction steps. Furthermore, late-stage modification of the obtained products successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.
- Xu, Cheng,Yin, Guodong,Jia, Feng-Cheng,Wu, Yan-Dong,Wu, An-Xin
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p. 2559 - 2564
(2021/04/13)
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- Iodine-Promoted Formal [3+2] Cycloaddition of Enaminone: Access to 2-Hydroxy-1,2-dihydro-pyrrol-3-ones with Quaternary Carbon Center
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A novel iodine promoted cyclization of enaminone with aryl methyl ketones has been developed as a straightforward method for constructing 2-hydroxy-pyrrol-3(2H)-ones. This strategy affords structurally diverse 2-hydroxy-pyrrol-3(2H)-ones rings in high yields. Moreover, a quarternary alcohol has been constructed efficiently in the reaction. Product purification required only washing with CH2Cl2 solvent, thereby avoiding traditional chromatography and recrystallization, making this an example of group-assisted purification chemistry.
- Yu, Xiao-Xiao,Zhao, Peng,Zhou, You,Huang, Chun,Wang, Li-Sheng,Wu, Yan-Dong,Wu, An-Xin
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p. 12141 - 12147
(2021/09/07)
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- Iodine-Promoted Multicomponent Synthesis of 2,4-Diamino-1,3,5-triazines
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A novel and efficient multicomponent cyclization of methyl ketones, cyanamides, and arylamines for the synthesizing 2,4-diamino-1,3,5-triazines via consecutive formation of four C-N bonds is reported. This multicomponent reaction is characterized by the employment of two molecules of cyanamide for double C(sp3)-H amination of methyl ketones, avoiding complicated prepreparation of substrates and expanding the substrate scope. Furthermore, this multicomponent cyclization strategy provides a new approach for generating diverse 2,4-diamino-1,3,5-triazines with a broad substrate scope under mild conditions.
- Zhao, Peng,Zhou, You,Yu, Xiao-Xiao,Huang, Chun,Wu, Yan-Dong,Yin, Guodong,Wu, An-Xin
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supporting information
p. 8528 - 8532
(2020/11/03)
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- Direct Synthesis of 2,3-Diaroyl Quinolines and Pyridazino[4,5- b]quinolines via an I2-Promoted One-Pot Multicomponent Reaction
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The first synthesis of 2,3-diaroyl quinolines via a formal [3 + 2 + 1] cycloaddition of enaminones, aryl methyl ketones, and aryl amines is disclosed. This reaction efficiently affords a 1,4-dicarbonyl scaffold, which is a useful building block for constructing complex fused heterocycles. Furthermore, the 1,4-dicarbonyl scaffold has been used directly to prepare pyridazino[4,5-b]quinoline skeletons in one-pot.
- Zhao, Peng,Wu, Xia,Zhou, You,Geng, Xiao,Wang, Can,Wu, Yan-Dong,Wu, An-Xin
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p. 2708 - 2711
(2019/04/17)
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- Iodine-Promoted N-H/α,β-C(sp3)-Trifunctionalization of l -Proline: Access to 3,4-Dihydrobenzo[ b][1,7]naphthyridines via Consecutive Decarboxylation/Ring Opening/Dicyclization
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A N-H/α,β-C(sp3)-trifunctionalization of l-proline, proceeding through an iodine-promoted consecutive decarboxylation/ring-opening/dicyclization process, is achieved. This strategy affords structurally diverse fused N-heterocycles in good yields with a wide substrate scope. Preliminary mechanistic studies indicate that catabolism of l-proline might be involved in this cascade reaction and the in situ generated intermediate 4-aminobutanal was identified as the key intermediate. Notably, this domino strategy enriches the reactivity of versatile l-proline in the synthesis of fused heterocycles.
- Geng, Xiao,Wang, Can,Zhao, Peng,Zhou, You,Wu, Yan-Dong,Wu, An-Xin
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p. 4939 - 4943
(2019/07/03)
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- I2-Promoted Multicomponent Dicyclization and Ring-Opening Sequences: Direct Synthesis of Benzo[ e][1,4]diazepin-3-ones via Dual C-O Bond Cleavage
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A novel and efficient formal [4 + 2+1] annulation of aryl methyl ketones and 2-aminobenzyl alcohols for the synthesis of benzo[e][1,4]diazepin-3-ones is reported. This reaction successfully affords diverse seven-membered ring lactams via dual C-O bond cleavage. A preliminary mechanistic study showed that a multicomponent dicyclization and ring-opening sequence might occur, with the introduction of methyl sulfide proposed as the last step. This efficient strategy with mild reaction conditions and a broad substrate scope has potential applications in chemistry and medicine.
- Geng, Xiao,Wang, Can,Huang, Chun,Zhao, Peng,Zhou, You,Wu, Yan-Dong,Wu, An-Xin
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p. 7504 - 7508
(2019/10/02)
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- Synthesis of Pyrrole-2-carbaldehyde Derivatives by Oxidative Annulation and Direct Csp3-H to C - O Oxidation
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An efficient and practical de novo synthesis of pyrrole-2-carbaldehyde skeletons featuring oxidative annulation and Csp3-H to C - O oxidation is presented, exemplified by the preparation of pyrrole-2-carbaldehyde derivatives from aryl methyl ketones, arylamines, and acetoacetate esters. Preliminary mechanistic investigations indicate that the aldehyde oxygen atom originates from oxygen. Moreover, the developed scalable approach provides a distinct advantage over traditional oxidative functionalization of C-H moieties, avoiding the use of stoichiometric quantities of hazardous oxidants.
- Wu, Xia,Zhao, Peng,Geng, Xiao,Wang, Can,Wu, Yan-Dong,Wu, An-Xin
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p. 688 - 691
(2018/02/09)
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- Iodine-promoted five-component reaction using fragment assembly strategy to construct dihydrooxepines
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An iodine-promoted fragment assembly strategy for the synthesis of fused heterocycles has been established. It provides an efficient route to construct pyrazolone-oxepine-pyrazoles from phenylhydrazines, aryl methyl ketones and acetoacetate esters. Notably, acetoacetate esters play two distinct pivotal roles in the five-component reaction by realizing the unique reactivities of methyl, methylene and carbonyl groups to construct 3-methyl-5-pyrazolone skeletons and by the reaction of methyl and carbonyl groups to form a C (sp3)-O bond.
- Zhao, Peng,Wu, Xia,Geng, Xiao,Wang, Can,Wu, Yan-Dong,Wu, An-Xin
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p. 4323 - 4330
(2018/07/06)
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- Gabapentin-base synthesis and theoretical studies of biologically active compounds: N-cyclohexyl-3-oxo-2-(3-oxo-2-azaspiro[4.5] decan-2-yl)-3-arylpropanamides and N-(tert-butyl)-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)-2-arylacetamide derivatives
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An intermolecular Ugi reaction of 2-(1-(aminomethyl)cyclohexyl)acetic acid (gabapentin) with glyoxal and cyclohexyl isocyanide or aromatic aldehyde and tertbutyl isocyanide under mild conditions in ethanol have been developed to produce two novel class of N-cyclohexyl-3-(aryl)-3-oxo-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)propanamideins and N-(tert-butyl)-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)-2-arylacetamide derivatives in good to excellent yields. This presents the first report for the intermolecular Ugi three component reaction of gabapentin, glyoxal, and an isocyanide. Also according to the theoretical studies the electron-donating groups increase the strength of intramolecular hydrogen bond and electron-withdrawing groups decrease the strength of intramolecular hydrogen bond.
- Amirani Poor, Mahboobe,Darehkordi, Ali,Anary-Abbasinejad, Mohammad,Mohammadi, Marziyeh
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- Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones
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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
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supporting information
p. 6998 - 7003
(2018/10/17)
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- One-Pot Synthesis of p-Amino-Substituted Unsymmetrical Benzils and Benzil Derivatives
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An efficient iodine/copper(II) oxide co-promoted direct oxidative coupling of anilines and methyl aryl ketones has been developed for the synthesis of p-amino-substituted unsymmetrical benzils and their iodo-substituted derivatives. The chemoselectivity of the reactions can be easily controlled by adjusting the amount of iodine. This method exhibits good functional group tolerance for various substituents on the aromatic rings of the methyl aryl ketones. A possible mechanism for this reaction has been proposed based on control experiments. A couple of representative quinoxalines were synthesized from the benzil products in order to demonstrate the utility of this approach. (Figure presented.).
- Zhang, Hongjin,Ren, Xiangwei,Zhao, Wentao,Tang, Xiangyang,Wang, Guangwei
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p. 395 - 401
(2017/02/10)
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- Direct Oxidative Cleavage of Multiple Csp3-H Bonds and a C-C Bond in 2-(Pyridin-2-yl)acetate Derivatives: Formal [3 + 1 + 1] Synthesis of 3-(Pyridin-2-yl)indolizine Skeletons
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A novel iodine-promoted oxidative cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and methyl ketones via the cleavage of multiple Csp3-H bonds has been developed, which also achieved efficient cleavage of a C-C bond in the 2-(pyridin-2-yl)acetate derivatives. This protocol represents an elegant molecular fragment assembly of diverse 3-(pyridin-2-yl)indolizines via a formal [3 + 1 + 1] annulation. Notably, the pyridine derivatives serve two pivotal roles to provide two fragments to construct 3-(pyridin-2-yl)indolizine skeletons, rather than the single role in building common indolizines.
- Wu, Xia,Zhao, Peng,Geng, Xiao,Zhang, Jingjing,Gong, Xingxing,Wu, Yan-Dong,Wu, An-Xin
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p. 3319 - 3322
(2017/06/23)
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- A C-H Oxidation/Two-Fold Cyclization Approach to Imidazopyridoindole Scaffold under Mild Oxidizing Conditions
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An expeditious one-step synthesis of the imidazopyridoindole scaffold was achieved through the C-H oxidation/two-fold cyclization reaction of methyl ketone and tryptamine derivatives. Mild oxidizing conditions were employed to realize the efficient oxidation of C(sp3)-H bonds, while suppressing overoxidation of the intermediate and ensuring the cross-trapping of two in situ generated acylimine intermediates.
- Xiang, Jia-Chen,Wang, Zi-Xuan,Cheng, Yan,Ma, Jin-Tian,Wang, Miao,Tang, Bo-Cheng,Wu, Yan-Dong,Wu, An-Xin
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p. 13671 - 13677
(2017/12/15)
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- Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells
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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
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supporting information
p. 1660 - 1664
(2017/04/04)
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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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- Catalytic asymmetric Meerwein-Ponndorf-Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)3 complex
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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
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supporting information
p. 3232 - 3235
(2017/03/20)
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- Naphthol synthesis: Annulation of nitrones with alkynes: Via rhodium(III)-catalyzed C-H activation
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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
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supporting information
p. 9640 - 9643
(2017/09/01)
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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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- 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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- Direct Construction of 4-Hydroxybenzils via Para-Selective C-C Bond Coupling of Phenols and Aryl Methyl Ketones
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A highly para-selective C-C bond coupling is presented between phenols C(sp2) and aryl methyl ketones C(sp3), which enables the direct construction of 4-hydroxybenzil derivatives. This practical method exhibits a broad substrate scop
- Xiang, Jia-Chen,Cheng, Yan,Wang, Miao,Wu, Yan-Dong,Wu, An-Xin
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p. 4360 - 4363
(2016/10/09)
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- Keto-Enol Thermodynamics of Breslow Intermediates
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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
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supporting information
p. 5044 - 5051
(2016/05/19)
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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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- Reversible addition and elimination of alcohols by vicinal tetracarbonyl compound
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In this Letter, we report reversible addition and elimination of alcohols by acyclic vicinal tetracarbonyl compounds. First, the reversible fixation and release behavior of alcohols by an acyclic vicinal tetracarbonyl compound, 1,4-diphenyl-1,2,3,4-butanetetraone (DPBT) was investigated. On the basis of the results, the addition of alcohol to DPBT was carried out to provide the alcohol adduct of DPBT, which has a hemiacetal structure. Furthermore, we discovered the reaction of DPBT with 2 equi amount of methanol.
- Maeda, Shinya,Sudo, Atsushi,Endo, Takeshi
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p. 1061 - 1065
(2018/03/24)
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- Coproduct promoted povarov reaction: Synthesis of substituted quinolines from methyl ketones, arylamines, and α-ketoesters
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A highly efficient I2-catalyzed Povarov-type reaction of methyl ketones, arylamines, and α-ketoesters is developed. This reaction utilizes a catalytic amount of HI coproduct as a promoter for the synthesis of substituted quinolones. This simple procedure represents an interesting new form of reactivity for the Povarov reaction with good functional group compatibility.
- Gao, Qinghe,Liu, Shan,Wu, Xia,Zhang, Jingjing,Wu, Anxin
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supporting information
p. 5984 - 5991
(2015/06/16)
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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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- 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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- One-pot three-component reactions of methyl ketones, phenols and a nucleophile: An expedient way to synthesize densely substituted benzofurans
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Three-component reactions of phenylglyoxal monohydrate, phenols, and indoles were developed with the aid of acid-catalyst, which produced various densely substituted benzofurans with good to excellent yields. On the basis of this observation, a one-pot, step-wise reaction was developed by using methyl ketones instead of using phenylglyoxal component in I2/DMSO system. At last, three-component reaction offered a useful way to synthesize densely substituted benzofurans starting from simple and easily available substrates. The indole component can be replaced by some other nucleophiles, such as 1,2,4-trimethoxybenzene and thiophenol.
- Cheng, Cheng,Liu, Changhui,Gu, Yanlong
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p. 8009 - 8017
(2015/12/31)
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- Metal-free, visible-light photoredox catalysis: Transformation of arylmethyl bromides to alcohols and aldehydes
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A mild, simple, and controllable metal-free photocatalytic system for the transformation of arylmethyl bromides to corresponding alcohols and aldehydes in high yields with visible-light irradiation has been achieved. Eosin Y was found to be an efficient promoter for this oxidative dehalogenation reaction under photo irradiation conditions.
- Li, Jian,Wang, Hongni,Liu, Li,Sun, Jiangtao
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p. 49974 - 49978
(2014/12/10)
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