1075-06-5Relevant articles and documents
A Facile and Effective Procedure for Synthesis of Polyfunctionalized Bis (imidazolyl) Pyrrole/Imidazolyl Indole from Pyrrole/Indole with Arylglyoxals and N-aryl amidines
Masoudi, Mozhgan,Shahbazi-Manshadi, Mohammad Reza,Anary-Abbasinejad, Mohammad
, p. 2772 - 2778 (2019)
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.
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
Khalafy, Jabbar,Etivand, Nasser,Poursattar Marjani, Ahmad,Khalillou, Neda
, p. 1857 - 1865 (2019)
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.
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
Arlan, Fatemeh Majidi,Khalafy, Jabbar,Maleki, Ramin
, p. 51 - 57 (2018)
[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.
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
Poursattar Marjani, Ahmad,Khalafy, Jabbar,Farajollahi, Ayda
, p. 268 - 274 (2019)
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.
The synthesis and ring opening of 3-aroyl(heteroaroyl)-1,2-dicyanocyclopropane-1,2-dicarboxylates
Karpov, Sergey V.,Kayukov, Yakov S.,Grigor'Ev, Arthur A.,Tafeenko, Victor A.
, p. 1732 - 1734 (2015)
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.
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
Javahershenas, Ramin,Khalafy, Jabbar
, p. 37 - 41 (2018)
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.
I2-promoted tandem cyclization to synthesize polysubstituted pyrano[3,2-c]chromene-2,5-diones
Cai, Qun,Zhuang, Shiyi,Yang, Mian,Peng, Na,Liu, Yi,Wu, Anxin
, (2019)
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
Synthesis of new indolylpyrrole derivatives via a four-component domino reaction between arylglyoxals, acetylacetone, indole and aliphatic amines in aqueous media
Mousavizadeh, Fereshteh,Talebizadeh, Mahdiyeh,Anary-Abbasinejad, Mohammad
, p. 2970 - 2974 (2018)
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.
A direct phosphine-mediated synthesis of polyfunctionalized pyrroles from arylglyoxals and β-enaminones
Masoudi, Mozhgan,Anary-Abbasinejad, Mohammad
, p. 103 - 104 (2016)
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.
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
Lu, Xin-Mou,Cai, Zhong-Jian,Li, Jian,Wang, Shun-Yi,Ji, Shun-Jun
, p. 51501 - 51507 (2015)
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.
A Green, Organometallic Catalyzed Synthesis of a Series of Novel Functionalized 4-Aroyl-4H-benzo[g]chromenes through One-pot, Three Component Reaction
Khalafy, Jabbar,Ilkhanizadeh, Siamand,Ranjbar, Masoumeh
, p. 951 - 956 (2018)
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.
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
Xu, Cheng,Yin, Guodong,Jia, Feng-Cheng,Wu, Yan-Dong,Wu, An-Xin
, p. 2559 - 2564 (2021/04/13)
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.
Iodine-Promoted Multicomponent Synthesis of 2,4-Diamino-1,3,5-triazines
Zhao, Peng,Zhou, You,Yu, Xiao-Xiao,Huang, Chun,Wu, Yan-Dong,Yin, Guodong,Wu, An-Xin
supporting information, p. 8528 - 8532 (2020/11/03)
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.
