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1.
Efficient One‐Pot Solvent‐Free Synthesis of 1H‐Pyrazolo[1,2‐b]phthalazine‐5,10‐diones Catalyzed by Sulfonic Acid Functionalized Nanoporous Silica (SBA‐Pr‐SO3H)
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Ghodsi Mohammadi Ziarani Nina Hosseini Mohtasham Alireza Badiei Negar Lashgari 《中国化学会会志》2014,61(9):990-994
A green protocol has been developed for the synthesis of 1H‐pyrazolo[1,2‐b]phthalazine‐5,10‐diones by one‐pot cyclocondensation reaction of phthalhydrazide, aromatic aldehydes, and malononitrile or ethyl cyanoacetate using sulfonic acid functionalized SBA‐15 (SBA‐Pr‐SO3H) as a heterogeneous solid acid catalyst under solvent‐free conditions. 相似文献
2.
《Journal of heterocyclic chemistry》2017,54(2):1048-1053
A simple and efficient one‐pot synthesis of interesting arylhydrazonals could be achieved via coupling of acetylacetaldehyde dimethyl acetal with aromatic diazonium salts. Dimroth type rearrangement was observed during the reaction of the arylhydrazonals with malononitrile or ethyl cyanoacetate leading to the formation of arylazonicotinic acid derivatives. The reaction of arylhydrazonals with malononitrile and aldehydes in the presence of DABCO afforded 4‐styryl‐1,2‐dihydropyridine‐3‐carbonitrile whose structure was established by X‐ray crystallography. Pyrazolyl‐enaminone was accomplished and used as a scaffold to synthesize bioactive fused heterocyclic compounds such as 1,2,4‐triazolo[1,5‐a ]pyrimidine 28 , benzo[4,5]imidazo[1,2‐a ]pyrimidine 30 and pyrazole[1,5‐a ]pyrimidine derivatives 32 . 相似文献
3.
Gopal Senthil Kumar Matthias Zeller Michael A. Frasso Karnam Jayarampillai Rajendra Prasad 《Journal of heterocyclic chemistry》2015,52(3):926-930
An efficient and economical method has been developed for the synthesis of pyrano[3,2‐h]quinolines via an indium trichloride‐catalyzed one‐pot three‐component reaction of 8‐hydroxyquinoline with aromatic aldehydes and malononitrile/ethyl cyanoacetate under microwave irradiation. 相似文献
4.
Magnetic Nanoparticle Supported Ionic Liquid Assisted Green Synthesis of Pyrazolopyranopyrimidines and 1,6‐diamino‐2‐oxo‐1,2,3,4‐tetrahydropyridine‐3,5‐ dicarbonitriles
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A simple and eco‐friendly green protocol was used for synthesis of pyrazolopyranopyrimidines via four‐component reaction of hydrazine hydrate, ethyl acetoacetate, barbituric acid or dimethyl barbituric acid, and aromatic aldehydes under thermal and solvent‐free conditions in the presence of magnetic nanoparticle supported silica bonded n‐propyl‐4‐aza‐1‐azoniabicyclo[2.2.2]octane chloride (MNPs@DABCO+Cl?) as an efficient, recyclable heterogeneous catalyst. MNPs@DABCO+Cl? also catalyzed the synthesis of 1,6‐diamino‐2‐oxo‐1,2,3,4‐tetrahydropyridine‐3,5‐dicarbonitrile derivatives by four‐component reaction of hydrazine hydrate, malononitrile, ethyl cyanoacetate and ketones under thermal and solvent‐free conditions at 80 °C. These methods are practical and offer many advantages, such as high yields, short reaction times, and simple work‐up. 相似文献
5.
《中国化学会会志》2017,64(8):889-895
In this paper, we report the use of bamboo rice husk ash as an efficient, greener, reusable, and biodegradable heterogeneous catalyst for the synthesis of tetrahydro‐4H ‐chromene‐3‐carbonitriles via the one‐pot three‐component reaction of malononitrile with aromatic aldehydes and dimedone or 1,3‐cyclohexanedione. The formation of bamboo rice husk ash‐silica has been confirmed by several analytical techniques. 相似文献
6.
The catalytic performance of the superparamagnetic nanocatalyst Fe3O4@SiO2@Sulfated boric acid as a green, recyclable, and acidic solid catalyst in the synthesis of chromeno[4,3,2‐de][1,6]naphthyridine derivatives has been studied. Chromeno[4,3,2‐de][1,6]naphthyridine derivatives via a pseudo four‐component reaction from aromatic aldehydes (1 mmol), malononitrile (2 mmol), and 2′‐hydroxyacetophenone in the presence of Fe3O4@SiO2@Sulfated boric acid (0.004 g) as a nanocatalyst in 3 mL of water as a green solvent at 80°C has been synthesized. The advantages of this method are higher product yields in shorter reaction times, easy recyclability and reusability of the catalyst, and easy work‐up procedures. The nanocatalyst was reused at least six times. The nanocatalyst retained its stability in the reaction, and after reusability, it was separated easily from the reaction by an external magnet. 相似文献
7.
Imidazo[1,2‐a]pyridines have been successfully synthesized in moderate to good yields via a tandem three‐component reaction of ethyl 2‐(3‐oxo‐3‐arylpropanethioamido)acetates with aromatic aldehydes and malononitrile by means of microwave irradiation using DABCO as the catalyst. The advantages of this method including high chemo‐ and regioselectivity make this new strategy highly attractive. 相似文献
8.
DABCO (1,4‐diazabicyclo[2.2.2]octane)‐modified magnetite with silica‐MCM‐41 shell (Fe3O4@silica‐MCM‐41@DABCO) as an effective, magnetic and novel heterogeneous reusable nanocatalyst was synthesized and analysed using various techniques. Evaluation of the catalytic activity of this nanocatalyst was performed in the clean synthesis of substituted 2‐aminodihydropyrano[3,2‐b]pyran‐3‐cyano in high yields via in situ reaction of azido kojic acid, malononitrile and various aldehydes. 相似文献
9.
Knoevenagel‐Michael‐cyclocondensation Tandem Reaction of Malononitrile,Various Aldehydes and Dimedone Catalyzed by Sulfonic Acid Functionalized Pyridinium Chloride as a New Ionic Liquid and Catalyst
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Mohammad Ali Zolfigol Ardeshir Khazaei Ahmad Reza Moosavi‐Zare Javad Afsar Vahid Khakyzadeh Omid Khaledian 《中国化学会会志》2015,62(5):398-403
New ionic liquid sulfonic acid functionalized pyridinium chloride [Pyridine–SO3H]Cl was used for the synthesis of tetrahydrobenzo[b]pyran derivatives by the one‐pot three component condensation reaction of various aldehydes, dimedone and malononitrile at 95 ºC under solvent‐free conditions. 相似文献
10.
《中国化学会会志》2017,64(3):331-336
Hexahydroquinolines are synthesized via one‐pot, four‐component condensation of 1,3‐cyclic diketones, aromatic aldehydes, malononitrile, and ammonium acetate in the presence of sulfamic acid‐functionalized nano‐titanium dioxide as a novel type of heterogeneous nanocatalyst. The optimized reaction condition is achieved using response surface method (Box–Behnken design [BBD ]). Operational simplicity, low cost, nontoxic nature, and high reusability of the catalyst together with simple work‐up and excellent product yields are the main advantages of this methodology. Also, the nanocatalyst can be recovered easily by centrifugation and reused efficiently for at least seven consecutive runs. 相似文献
11.
A. A. Shestopalov L. A. Rodinovskaya A. M. Shestopalov V. P. Litvinov 《Russian Chemical Bulletin》2004,53(10):2342-2344
A single-step method for the synthesis of substituted 7-aminopyrano[2,3-d]pyrimidines was developed. The method involves a three-component reaction of barbituric acid or 4,6-dihydroxypyrimidine with aromatic aldehydes and malononitrile in DMF in the presence of N-methylmorpholine as a catalyst.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2242–2244, October, 2004. 相似文献
12.
《合成通讯》2013,43(24):4557-4563
Abstract 6‐Amino‐5‐cyano‐4‐aryl‐1,4‐dihydropyrano[2,3‐c]pyrazoles were synthesized by three‐component reaction of aromatic aldehydes, malononitrile, and 3‐methyl‐1‐phenyl‐2‐pyrazolin‐5‐one using triethylbenzylammonium chloride (TEBA) as catalyst in aqueous media. The reaction has the advantages of good yield, less pollution, ease of separation, and of being environment friendly. 相似文献
13.
《应用有机金属化学》2017,31(2)
An immobilized Co (II) Schiff base complex supported on multi‐wall carbon nanotubes was synthesized and characterized using Fourier transform infrared spectroscopy, X‐ray diffraction, scanning electron microscopy, energy‐dispersive X‐ray spectroscopy , thermogravimetric analysis and inductively coupled plasma mass spectrometry. It was shown that the supported complex is a facile, eco‐friendly, recyclable, reusable and green catalyst for three‐component condensation of 2‐naphthol and acetamide with various aldehydes for the synthesis of 1‐amidoalkyl‐2‐naphthol derivatives under solvent‐free conditions. Also, in a further study, the catalytic application was studied in the synthesis of tetrahydrobenzo[b ]pyran derivatives via the condensation reaction of malononitrile and dimedone with several aromatic aldehydes. The procedures suggested here for the synthesis of 1‐amidoalkyl‐2‐naphthol and tetrahydrobenzo[b ]pyran derivatives offer several advantages, such as stability, recyclability and eco‐friendliness of the catalyst, simple experimental conditions, short reaction times, high to excellent yields and easy work‐up. 相似文献
14.
6‐Amino‐4‐aryl‐5‐cyanopyrazolo[3,4‐b]pyridines were synthesized by a three‐component reaction of aromatic aldehydes, malononitrile, and 5‐amino‐3‐methyl‐1‐phenylpyrazole using sodium 1‐dodecanesulfonic (SDS) as catalyst in aqueous media. The reaction has the advantages of good yields, less pollution, ease of separation, and environmental friendliness. 相似文献
15.
One‐Pot Green Synthesis of Thiazolo[3,2‐a]pyridine Derivatives via Tandem Cyclization in Aqueous Media
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Muthusamy Boominathan Muthupandi Nagaraj Chellaiah Maheshwaran Shanmugam Muthusubramanian Nattamai Bhuvanesh 《Journal of heterocyclic chemistry》2014,51(1):244-248
Facile, three‐component domino reactions of readily available thioglycolic acid/ethyl thioglycolate, aromatic aldehydes, and malononitrile/ethyl cyanoacetate in aqueous potassium carbonate at room temperature afforded thiazolo[3,2‐a]pyridine derivatives chemoselectively in good to excellent yield. All the formed 4H‐chromenes were characterized by spectral and X‐ray methods. 相似文献
16.
Water Mediated Domino Knoevenagel‐Michael‐cyclocondensation Reaction of Malononitrile,Various Aldehydes and Barbituric Acid Derivatives Using Boric Acid Aqueous Solution System Compared with Nano‐titania Sulfuric Acid
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Nano‐titania sulfuric acid (TSA) and boric acid [B(OH)3] were efficiently utilized for domino Knoevenagel‐Michael‐cyclocondensation reaction of malononitrile, various aldehydes and barbituric acid derivatives to synthesis of pyrano[2,3‐d]pyrimidine diones. It is interesting that in boric acid aqueous solution system, H+ which abstracted from water by the interaction with B(OH)3, efficiently catalyzed the reaction. 相似文献
17.
Isatin‐SO3H coated on amino propyl modified magnetic nanoparticles (Fe3O4@APTES@isatin‐SO3H) is found to be a novel, efficient, and reusable magnetic nanocatalyst, and characterized by FT‐IR, SEM, TEM, XRD, EDX, VSM, and TGA analysis. The magnetic nanocatalyst demonstrated outstanding performance in synthesis of pyrano[2,3‐d] pyrimidines derivatives via one‐pot three‐component reaction of various aromatic aldehydes 1, malononitrile 2, and barbituric acid 3 under reflux conditions in mixture of H2O:EtOH (1:1) as solvent. Easy workup procedure, short reaction time, high yield, simple preparation and easy recovery of the catalyst, mild reaction conditions are some advantages of this work. 相似文献
18.
Efficient and Expeditious Synthesis of Pyrano‐pyrimidines,Multi‐substituted γ‐Pyrans,and Their Antioxidant Activity
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Khairy A. M. El‐Bayouki Wahid M. Basyouni Tamer K. Khatab Fakhry A. El‐Basyoni Ahmed R. Hamed Eslam A. Mostafa 《Journal of heterocyclic chemistry》2014,51(1):106-115
An efficient, expeditious catalytic route for the synthesis of ethyl 6‐amino‐5‐cyano‐2‐methyl‐4‐aryl‐4H‐pyran‐3‐carboxylates 2 was achieved via a three‐component, one‐pot reaction of malononitrile, ethyl acetoacetate, and various aromatic aldehydes in water as a solvent at room temperature. The key advantages are excellent yield, reaction time, and inexpensive catalyst. Also, cyclization of 4H‐pyrans 2 to the corresponding 4H‐pyrano[2,3‐d]pyrimidines 3 using silica sulfuric acid in the presence of acetic anhydride was described. Some synthesized compounds exhibited promising antioxidant activities. 相似文献
19.
A new nano‐Fe3O4‐supported organocatalyst based on 3,4‐dihydroxypyridine: an efficient heterogeneous nanocatalyst for one‐pot synthesis of pyrazolo[3,4‐b]pyridines and pyrano[2,3‐d]pyrimidines
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A simple and practical strategy for the synthesis of a novel nano‐Fe3O4‐supported organocatalyst system based on 3,4‐dihydroxypyridine (Fe3O4/Py) has been developed. The prepared catalyst was characterized using Fourier transform infrared spectroscopy, transmission and scanning electron microscopies, X‐ray diffraction, vibrating sample magnetometry and energy‐dispersive X‐ray analysis. Accordingly, the Fe3O4/Py nanoparticles show a superparamagnetic property with a saturation magnetization of 61 emu g?1, indicating potential application in magnetic separation technology. Our experimental results reveal that the pyridine‐functionalized Fe3O4 nanoparticles are an efficient base catalyst for the domino condensation of various aromatic aldehydes, Meldrum's acid and 5‐methylpyrazol‐3‐amine under very mild reaction condition and in the presence of ethanol solvent. Moreover, the synthesized catalyst was used for one‐pot, three‐component condensation of aromatic aldehydes with barbituric acid and malononitrile to produce 7‐amino‐2,4‐dioxo‐5‐phenyl‐2,3,4,5‐tetrahydro‐1H‐pyrano[2,3‐d]pyrimidine‐6‐carbonitriles. All reactions are completed in short times and all products are obtained in good to excellent yields. Also, notably, the catalyst was reused five times without significant degradation in catalytic activity and performance. Copyright © 2016 John Wiley & Sons, Ltd. 相似文献
20.
A Mild and Environmentally Benign Synthesis of Tetrahydrobenzo[b]pyrans and Pyrano[c]chromenes Using Pectin as a Green and Biodegradable Catalyst
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Pectin was applied as a green and biodegradable catalyst for the one‐pot three‐component synthesis of tetrahydrobenzo[b]pyrans and pyrano[c]chromenes, from the condensation between aromatic aldehydes, malononitrile, and dimedone or 4‐hydroxycumarine at ambient temperature. This protocol has many advantages such as mild conditions, high yields, environmental benignity, simple work‐up procedures, short reaction time, as well as the use of a natural, easily accessible, convenient handling, and inexpensive catalyst. Another advantage of this method is that the products do not require further purification such as column chromatography. 相似文献