- Solvent Selective Polyacrylonitrile Fiber as a Recyclable Catalyst for the Knoevenagel-Michael Reaction in Water
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Heterogeneous catalysis is an important branch of sustainable chemistry. In this work, a series of polyacrylonitrile fiber (PANF) fiber catalysts (PANF-E, PANF-EDs, and PANF-D) with different catalytic micro-environments are developed and characterized by
- Li, Pengyu,Yang, Yu,Wu, Xueling,Lu, Jiali,Hu, Lingrui,Chen, Weihua,Zhang, Wenqin
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- Choline chloride-coated UiO-66-Urea MOF: A novel multifunctional heterogeneous catalyst for efficient one-pot three-component synthesis of 2-amino-4H-chromenes
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A new Zr-based MOF, namely, UiO-66-Urea, was prepared through polymerization between the 2-aminoterephthalate linkers of UiO-66-NH2 MOF and 1,4-phenylene diisocyanate under mild reaction conditions. Post-synthetic coating of UiO-66-Urea with ch
- Akbarian, Mohadeseh,Daliran, Saba,Oveisi, Ali Reza,Sanchooli, Esmael
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- Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyra-no_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazoli-dinedione derivatives
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In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180oC in a sealed autoclave in a
- Ghorbani, Fatemeh,Pourmousavi, Seied Ali,Kiyani, Hamzeh
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- Choline chloride/pentaerythritol: a deep eutectic solvent for the synthesis of pyran and chromene derivatives
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Abstract: A novel deep eutectic solvent system was prepared by mixing choline chloride as a hydrogen-bond acceptor with 2,2-bis(hydroxymethyl)propane-1,3-diol (pentaerythritol) as a hydrogen-bond donor. This green solvent was used for the one-pot synthesi
- Azimzadeh-Sadeghi, Setareh,Yavari, Issa
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p. 1261 - 1267
(2020/11/23)
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- Bipyridinium chloride supported rice husk silica: An efficient nanocomposite for the one-pot preparation of spirooxindole pyran and 2-amino-4h-chromene derivatives
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In this paper, rice-husk-silica supported n-propyl bipyridinium chloride (RHPrBPCl) has been prepared as a heterogeneous catalyst. RHPrBPCl has been successfully applied in the one-pot preparation of spirooxindole pyran and 2-amino- 4H-chromene derivative
- KIASAT, Ali Reza,HAMID, Sheida,SAGHANEZHAD, Seyyed Jafar
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p. 927 - 934
(2021/02/05)
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- Biocompatible Ionic Liquid Promote One-Pot Synthesis of 2-Amino-4H-Chromenes Under Ambient Conditions
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Abstract: The synthesis of 2-amino-4H-chromenes through one-pot multicomponent reactions has received great attention due to the high atom efficiency and the broad bioactivities of the products. Here, the catalytic performances of a series of functional ionic liquids towards this type of reaction were investigated and the results showed that the ionic liquid, choline acetate ([Choline][Ac]), could efficiently promote this reactions under room temperature without the necessary of organic solvents. The reaction is easy to be conducted and the following work-up procedures are very simple. The pure products can be obtained through extraction and washing procedures, no column separation procedures are needed. Intriguingly, this reaction system can be easily scaled up to multi-gram, suggesting its perspective in industrial applications. In addition, the ionic liquid [Choline][Ac] can be easily prepared from cheap and biocompatible materials, and it can be feasibly recycled and reutilized for at least five cycles. Graphic Abstract: Various aldehydes, malononitrile and activated phenols could be converted to thecorresponding 2-amino-4H-chromenes with good to excellent isolated yields underthe catalysis of choline acetate at room temperature. [Figure not available: see fulltext.]
- Zhu, Anlian,Li, Qixing,Feng, Wanlu,Fan, Dongshuang,Li, Lingjun
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p. 720 - 733
(2020/08/07)
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- A green route towards substituted 2-amino-4H-chromenes catalyzed by an organobase (TBD) functionalized mesoporous silica nanoparticle without heating
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1,5,7-Triazabicyclo-[4,4,0]-dec-1-ene functionalized mesoporous silica nanoparticle promoted one-pot multicomponent synthesis of 2-amino-4H-chromenes from a phenolic component, different aldehydes and malononitrile was achieved in aqueous media at room te
- Karmakar, Bikash,Nandi, Rajesh
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p. 2161 - 2172
(2021/04/22)
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- One-pot Synthesis of 2-Amino-4H-Chromenes using Chicken Eggshell Waste as Green Catalyst under Solvent-Free Conditions
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Chicken eggshell waste has been employed as green and efficient catalyst for the preparation of 2-amino-4H-chromenes. The aromatic aldehydes were condensed with malononitrile and 1-naphthol or 2-naphthol under solvent-free condition in the presence of chi
- Gadhave, Anil,Uphade, Bhagwat
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p. 387 - 394
(2021/01/25)
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- Organocatalytic Cascade Knoevenagel–Michael Addition Reactions: Direct Synthesis of Polysubstituted 2-Amino-4H-Chromene Derivatives
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Abstract: In this report, we documented novel strategy for the synthesis of bioactive polysubstituted 2-amino-4H-chromine derivatives under a heterogeneous Al-MCM-41-LDH@APTES (ALAM) catalysis. A synthetic procedure is developed to prepare Al-MCM-41-LDH@APTES (ALAM) heterogeneous basic catalysts. Mesoporous Al-MCM-41 is functionalized by known grafting chemistry via layered double hydroxide (LDH) nanosheets and (3-aminopropyl)triethoxysilane (APTES) moiety as a basic organocatalyst. The resulting catalysts contain amino group functionality on the external surface as well as inside the layers and the basicity can be tuned by the loading of APTES. The samples were fully characterized by 29Si and 13C CP/MAS NMR, infrared absorption spectroscopy, TEM, XPS, EDX, TGA, XRD, CO2-TPD, N2 adsorption isotherms measurements, and they were successfully examined for the cascade type Knoevenagel–Michael addition reactions. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The present catalytic method is simple and robust for diversity oriented synthesis which proceeds good to excellent yields without generating any hazards waste. The broad substrate scope, excellent functional group compatibility makes this protocol highly useful towards synthesis of polysubstituted α-cyanoacrylates, α-cyanoacrylonitriles and 2-amino-4H-chromenes with an electron-donating or electron-withdrawing group. We have also successfully established a flow reaction system, gram-scale synthesis as well as catalyst recyclability up to six catalytic cycles without appreciable loss of its activity. Graphic Abstract: [Figure not available: see fulltext.].
- Jadhav, Sanjay N.,Patil, Seema P.,Sahoo, Dipti Prava,Rath, Dharitri,Parida, Kulamani,Rode, Chandrashekhar V.
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p. 2331 - 2351
(2020/02/25)
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- An inorganic–organic hybrid material based on a Keggin-type polyoxometalate@Dysprosium as an effective and green catalyst in the synthesis of 2-amino-4H-chromenes via multicomponent reactions
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A novel inorganic–organic hybrid, [Dy4(PDA)4(H2O)11(SiMo12O40)]·7H2O denoted as (POM@Dy-PDA), based on a lanthanide cluster, a Keggin-type polyoxomolybdate, and PDA (1,10-phenant
- Hosseinzadeh-Baghan, Sara,Mirzaei, Masoud,Eshtiagh-Hosseini, Hossein,Zadsirjan, Vahideh,Heravi, Majid M.,Mague, Joel T.
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- Synthesis and characterization of a novel Fe3O4@SiO2-BenzIm-Fc[Cl]/BiOCl nano-composite and its efficient catalytic activity in the ultrasound-assisted synthesis of diverse chromene analogs
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In this study, a novel magnetically recoverable Fe3O4@SiO2-BenzIm-Fc[Cl]/BiOCl nano-composite was synthesized using a simple chemical co-precipitation method. This is the first time that a magnetic nano-catalyst bearing ionic liquid, ferrocene and BiOCl is synthesized. The Fe3O4@SiO2-BenzIm-Fc[Cl]/BiOCl nano-composite was characterized by Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX) and field emission scanning electron microscopy (FE-SEM) techniques. The catalytic activities of the novel magnetic nano-composite were evaluated in one-pot three-component synthesis of a wide variety of 2-amino-3-cyano-4H-chromene derivatives under ultrasound irradiation. A simple, facile and highly efficient ultrasound-assisted method was developed to synthesize 4H-chromene derivatives via one-pot, three-component reaction of aldehyde, malononitrile and active phenolic compounds (2-naphthol, 1-naphthol, 3-(dimethylamino)phenol, resorcinol and orcinol) at room temperature. The reaction of aldehyde, malononitrile and orcinol is newly introduced in this paper. The ultrasound-assisted synthesis protocol that was studied in this article exhibits some notable advantages such as short reaction times, operational simplicity, green reaction conditions, high yields and easy work-up and purification steps. In addition, the novel magnetic nano-composite could be easily recovered by an external magnetic field and reused for six-reaction cycles without significant loss of its catalytic activity.
- Mohammadi, Reza,Esmati, Somayeh,Gholamhosseini-Nazari, Mahdi,Teimuri-Mofrad, Reza
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supporting information
p. 135 - 145
(2019/01/04)
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- A one-pot green synthesis of 2-amino-4H-benzo[h]chromenes catalyzed by a dioxomolybdenum Schiff base complex supported on magnetic nanoparticles as an efficient and recyclable nanocatalyst
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In this work, catalytic performance of a molybdenum Schiff base complex-supported magnetic support as a nanocatalyst was evaluated for the preparation of 2-amino-4H-benzo[h]chromenes through one-pot, three component reactions of 1-naphthol, various aldehydes, and malononitrile under solvent-free conditions. A promising greener and eco-friendly method with a short reaction time, high yield of products, and simple work-up procedure was achieved. The nanocatalyst could be easily separated and regenerated from reaction media by an external magnet and reused at least seven consecutive times with small drops in its catalytic performance.
- Aghajani, Milad,Monadi, Niaz
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p. 775 - 784
(2019/03/20)
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- Novel task-specific ionic liquid [Et2NH(CH2)2CO2H][AcO] as a robust catalyst for the efficient synthesis of some pyran-annulated scaffolds under solvent-free conditions
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A novel task-specific ionic liquid, 2-carboxy-N,N-diethylethanaminium acetate denoted as [Et2NH(CH2)2CO2H][AcO], is prepared in an easy process and fully characterized by using suitable methods such as FT-IR, 1H-NMR, 13C-NMR, and TG, DTG and DTA analyses. After preparation, the promoting ability of this catalyst for one-pot multicomponent synthesis of 2-amino-4H-chromenes, dihydropyrano[3,2-c]chromenes and dihydropyrano[2,3-c]pyrazoles using in situ-developed arylidenemalononitriles through Knoevenagel reaction under solvent-free conditions is described. The sustainable procedure, short reaction times (6–36?min), effortless work-up, non-chromatographic purification, good-to-excellent product yields (79–96%), ease of recovery and reusability of the catalyst up to six reaction runs without a decrease of activity are the notable features of the present protocol.
- Shaikh, Mohd Akmal,Farooqui, Mazahar,Abed, Syed
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p. 1595 - 1617
(2019/01/04)
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- An Eco-friendly Catalytic System for One-pot Multicomponent Synthesis of Diverse and Densely Functionalized Pyranopyrazole and Benzochromene Derivatives
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An external base-free, efficient, cost-effective, and environmentally benign protocol has been developed for the one-pot multicomponent synthesis of highly functionalized pyranopyrazoles and benzochromenes using water extract of Agave americana (century p
- Patil,Patil, Rupesh C.,Patil, Suresh S.
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- Triethanolamine-catalyzed expeditious and greener synthesis of 2-amino-4H-chromenes
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Triethanolamine (TEOA), an inexpensive and eco-friendly base, was used to efficiently catalyze the three-component condensation reaction of heterocyclic/aromatic aldehyde, (α/β)-naphthol, and malononitrile in water to give the corresponding substituted 2-
- Patel, Anilkumar S.,Tala, Satishkumar D.,Nariya, Pankajkumar B.,Ladva, Kartik D.,Kapuriya, Naval P.
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p. 247 - 252
(2018/10/31)
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- Zn(L-proline)2 as an efficient and reusable catalyst for the multi-component synthesis of pyran-annulated heterocyclic compounds
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We have developed a simple, straightforward and highly efficient multi-component one-pot synthesis of 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocyclic compounds. Zn(L-proline)2 has been utilized as a mild and efficient Lewis acid cata
- Tahmassebi, Daryoush,Blevins, John E.,Gerardot, Shori S.
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- Bipyridinium chloride supported rice husk silica: An efficient nanocomposite for the one-pot preparation of spirooxindole pyran and 2-amino-4H-chromene derivatives
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In this paper, rice-husk-silica supported n-propyl bipyridinium chloride (RHPrBPCl) has been prepared as a heterogeneous catalyst. RHPrBPCl has been successfully applied in the one-pot preparation of spirooxindole pyran and 2-amino-4H-chromene derivatives
- Hamid, Sheida,Kiasat, Ali Reza,Saghanezhad, Seyyed Jafar
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p. 927 - 934
(2020/06/27)
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- A molybdenum(VI) Schiff base complex immobilized on functionalized Fe3O4 nanoparticles as a recoverable nanocatalyst for synthesis of 2-amino-4H-benzo[h]chromenes
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A dioxomolybdenum(VI) complex of a Schiff base, immobilized on the surface of modified Fe3O4 with a silica coating, has been synthesized and characterized by spectroscopic and microscopic techniques including FTIR, TGA, ICP, SEM, EDX, VSM, and XRD analyses. The catalytic performance of this material has been evaluated for the preparation of 2-amino-4H-benzo[h]chromenes via the one-pot, three-component reaction of aldehydes, malononitrile, and 1-naphthol under solvent-free conditions. The benefits of this protocol are short reaction time, simple workup procedure, and high yields of products. Also, the synthesized nanocatalyst could be separated easily from the reaction mixture using an external magnet and reused for four consecutive times with only minor degradation of its catalytic performance.
- Monadi, Niaz,Moradi, Elham
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p. 161 - 170
(2018/02/06)
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- Synthesis and characterization of sodium polyaspartate-functionalized silica-coated magnetite nanoparticles: A heterogeneous, reusable and magnetically separable catalyst for the solvent-free synthesis of 2-amino-4H-chromene derivatives
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An efficient and facile method was used for the synthesis of sodium polyaspartate-functionalized silica-coated magnetite nanoparticles. The structure of this nanoparticle was characterized by scanning electron microscopies, X-ray diffraction, energy-dispe
- Mobinikhaledi, Akbar,Moghanian, Hassan,Ghanbari, Masoumeh
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- Design, synthesis, biological evaluation and in silico molecular docking studies of novel benzochromeno[2,3-d]thiazolopyrimidine derivatives
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Abstract: A new series of benzochromeno[2,3-d]thiazolopyrimidine derivatives were synthesized by involving 7-phenyl-10-thioxo-7,9,10,11-tetrahydro-8H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-ones with phenacyl bromide in the presence of p-toluenesulfonic acid
- Banoth, Sonyanaik,Boda, Sakram,Perugu, Shyam,Balabadra, Saikrishna,Manga, Vijjulatha
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p. 1833 - 1846
(2017/12/04)
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- Grinding synthesis of 2-AMINO-4H-chromenes using 3,3-(BUTANE-1,4-DIYL) BIS (1,2-DIMETHYL-1H-IMIDAZOLE-3-IUM)Br-CAN as a novel reagent
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A clean and environmentally benign route to 2-Amino-4H-chromenes has been developed via three-component condensation reaction of various benzyl alcohols, malononitrile and 1-naphthol, using a catalytical amount of CAN and a reusable ionic liquid 3,3-(Buta
- Nikpassand, Mohammad,Fekri, Leila Zare,Ahmadi, Parvin
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p. 3399 - 3402
(2017/05/22)
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- Preparation of a superior liquid catalyst by hybridization of three solids of nanoZnO, urea, and choline chloride for Knoevenagel-based reactions
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Abstract: The complex catalyst of [ZnClO.urea]?[Ch.urea]+ has been prepared by dissolving of nanoZnO in choline chloride:2urea at 50 °C. The concentration of [ZnClO.urea]? in the given liquid is 19,987 ppm and 10.5 times h
- Tamaddon, Fatemeh,Azadi, Davood
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p. 2077 - 2086
(2017/09/13)
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- Aqua one-pot, three-component synthesis of dihydropyrano[3,2-c]chromenes and amino-benzochromenes catalyzed by sodium malonate
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The widespread biological properties of dihydropyrano[3,2-c]chromenes, 2-amino-4-aryl-4H-benzo[h]chromenes, and 3-amino-1-aryl-1H-benzo[f]chromenes have led to increasing efforts for the development of tremendously effective synthetic protocols aimed at their synthesis. In this contribution, sodium malonate was employed for the first time as an efficient catalyst for the one-pot, three-component tandem Knoevenagel–cyclocondensation reaction of 4-hydroxycoumarin (or naphthols), malononitrile/ethyl cyanoacetate, and various aldehydes. These compounds underwent Knoevenagel–Michael–Thorpe–Ziegler cyclization upon heating at 70?°C in water to give the respective medicinally relevant dihydropyrano[3,2-c]chromenes and amino-benzochromenes. The method is versatile and amenable to many substrates as it requires no specialized devices such as microwave, ultrasound and ball-milling. Also, the salient features of this high-yielding protocol are green reaction conditions, the use of commercially available catalyst, easy purification processes by a simple filtration, and relatively shorter reaction times.
- Kiyani, Hamzeh,Tazari, Mohsen
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p. 6639 - 6650
(2017/10/06)
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- One-pot synthesis of some 2-amino-4H-chromene derivatives using triethanolamine as a novel reusable organocatalyst under solvent-free conditions and its application in electrosynthesis of silver nanoparticles
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A wide variety of 2-amino-4H-chromene derivatives with diverse substituents on the 4H-chromene ring were efficiently prepared via one-pot three-component reaction of an aromatic aldehyde and malononitrile with 2-hydroxynaphthalene-1,4-dione, ethyl acetoac
- Maleki,Baghayeri,Sheikh,Babaee,Farhadi
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p. 1064 - 1072
(2017/06/29)
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- Aegle marmelos in heterocyclization: Greener, highly efficient, one-pot three-component protocol for the synthesis of highly functionalized 4 H -benzochromenes and 4 H -chromenes
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A facile, one-pot three-component protocol for the synthesis of 2-amino-4H-chromene derivatives has been demonstrated using Bael Fruit Extract (BFE) as a natural catalyst in a green reaction medium. This method offers a mild, efficient and highly economic
- Shinde, Sachin,Damate, Shashikant,Morbale, Smita,Patil, Megha,Patil, Suresh S.
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p. 7315 - 7328
(2017/02/05)
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- SBA-15@methenamine-HPA: a novel, simple, and efficient catalyst for one-pot three-component synthesis of 2-amino-4H-chromene derivatives in aqueous medium
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Abstract: Cl-functionalized SBA-15 was reacted with methenamine and subsequently applied for embedding heteropolyacids. The novel catalyst, SBA-15@methenamine-HPA, was characterized by using scanning electron microscopy (SEM) with energy-dispersive X-ray
- Sadjadi, Samahe,Heravi, Majid M.,Zadsirjan, Vahideh,Ebrahimizadeh, Maryam
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p. 5467 - 5483
(2017/09/23)
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- One-pot catalytic multicomponent synthesis of chromene derivatives by 1-Allyl-3-Methyl-Imidazolium halides
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2-amino-3-cyano-4-aryl-4H-benzo[h]chromenes and 2-amino-3- cyano-1-aryl-1H-benzo[f] chromenes were obtained in a one-pot three-component reaction of a or β-naphthol (1a and 1b), aromatic aldehydes (2a-n), malononitrile (3) in the presence of 1-allyl-3-met
- Azizkhani, Vahid,Amirloo, Mohammad Reza,Mohammadi, Bagher,Moradi, Ali Reza
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p. 831 - 837
(2018/04/09)
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- Synthesis of 2-amino-3-cyano 4-H-chromenes containing quinoline in water: computational study on substituent effects
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An efficient, high yielding and environmentally benign strategy to the synthesis of new 2-amino-3-cyano-4-H-chromene derivatives, via one-pot three-component reaction involving malononitrile, various α- or β-naphthol and appropriate aromatic aldehydes inc
- Heravi, Majid M.,Hosseinnejad, Tayebeh,Faghihi, Zeinab,Shiri, Morteza,Vazinfard, Mahdiyeh
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p. 823 - 832
(2017/02/26)
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- Studies on the synthesis of substituted 2-amino-4H-benzo[h]chromene and 3-amino-1H-benzo[f]chromene derivatives using base supported ionic liquid like-phase (SILLP) as an efficient green catalyst
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The synthesis of several substituted 2-amino-4H-benzo[h]chromene and 3-amino-1H-benzo[f]chromene derivatives was carried out using a one-pot three-component reaction of an arylaldehyde, malononitrile and a naphthol in H2O and in the presence of
- Kheirkhah, Leila,Mamaghani, Manouchehr,Mahmoodi, Nosrat Ollah,Yahyazadeh, Asieh,Ziabari, Seyedeh Saeedeh Mirnezami
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- Synthesis, screening and docking of fused pyrano[3,2-d]pyrimidine derivatives as xanthine oxidase inhibitor
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In view of developing effective xanthine oxidase (XO) enzyme inhibitors, a series of 100 pyrano[3,2-d]pyrimidine derivatives was synthesized and evaluated for its in vitro XO enzyme inhibition. Structure activity relationship has also been established. Am
- Kaur, Manroopraj,Kaur, Amandeep,Mankotia, Suhani,Singh, Harbinder,Singh, Arshdeep,Singh, Jatinder Vir,Gupta, Manish Kumar,Sharma, Sahil,Nepali, Kunal,Bedi, Preet Mohinder Singh
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- Diisopropyl azodicarboxylate mediated selective dehydrogenation of 2-amino-3-cyano 4H-chromenes
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Selective dehydrogenation of 2-amino-3-cyano 4H-chromenes to the corresponding 2-iminochromenes mediated by diisopropyl azodicarboxylate under neutral conditions is reported. The dehydrogenation reaction is compatible with phenolic hydroxyl group and gene
- Sharma, Himanshu,Mourya, Mohini,Guin, Debanjan,Joshi, Yogesh C.,Dobhal, Mahabeer P.,Basak, Ashok K.
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p. 1727 - 1732
(2017/04/13)
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- Synthesis of a novel poly(ethylene glycol) grafted triethylamine functionalized dicationic ionic liquid and its application in one-pot synthesis of 2-amino-2-chromene derivatives in water
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A novel poly(ethylene glycol) grafted triethylamine functionalized dicationic ionic liquid has been prepared and characterized. It was successfully used as an efficient catalyst for the three-component synthesis of 2-amino-2-chromene derivatives in water.
- Wang, Yinglei,Yue, Chun,Li, Xia,Luo, Jun
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p. 1021 - 1026
(2016/08/08)
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- Application of {[4,4′-BPyH][C(CN)3]2} as a Bifunctional Nanostructured Molten Salt Catalyst for the Preparation of 2-Amino-4 H -chromene Derivatives under Solvent-Free and Benign Conditions
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The bifunctional nanostructured molten salt [4,4′-bipyridine]-1,1′-diium tricyanomethanide has been employed as a highly efficient and powerful catalyst for the preparation of 2-amino-4H-chromenes. A wide variety of aromatic aldehydes was condensed with m
- Zolfigol, Mohammad Ali,Yarie, Meysam,Baghery, Saeed
-
supporting information
p. 1418 - 1422
(2016/06/01)
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- Polystyrene-supported basic dicationic ionic liquid as a novel, reusable, and efficient heterogeneous catalyst for the one-pot synthesis of chromene derivatives in water
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Polystyrene-supported 1,4-bis(3-methylimidazolium-1-yl)butane dihydroxide basic dicationic ionic liquid was prepared by supporting the ionic liquid onto highly cross-linked chloromethylated polystyrene. FT-IR, SEM, TG-DTA, and elemental analysis were empl
- Heidarizadeh, Fariba,Taheri, Narges
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p. 3829 - 3846
(2016/04/05)
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- CaO-ZrO2 nanocomposite oxide prepared by urea hydrolysis method as heterogeneous base catalyst for synthesis of chromene analogues
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A series of CaO–ZrO2 nanocomposite oxides containing 2–50?mol% of CaO were synthesized employing urea as a mild hydrolyzing agent. The nanocomposite systems were characterized using XRD, Fourier analysis, TPD, Raman, XPS, TGA-DSC, FESEM, HRTEM,
- Pradhan, Sagnika,Sahu, Vivekananda,Mishra
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p. 297 - 309
(2016/12/07)
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- Application of novel multi-cationic ionic liquids in microwave assisted 2-amino-4H-chromene synthesis
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Novel multi-cationic ionic liquids containing a mesitylene backbone with acetate and methane sulphonate anions have been synthesized. These ionic liquids were used for the synthesis of 2-amino-4H-chromenes under microwave heating. The effects of nature and amount of ionic liquids on the yield and reaction time were thoroughly investigated. The ionic liquids showed a considerable level of reusability without a significant decrease in catalytic activity. We have successfully combined the advantages of microwave technology with ionic liquids to facilitate the rapid construction of chromene skeletons from readily obtainable and inexpensive materials via a multicomponent strategy.
- Kumbhar, Arjun,Jadhav, Sanjay,Shejwal, Rajendra,Rashinkar, Gajanan,Salunkhe, Rajshri
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p. 19612 - 19619
(2016/03/01)
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- Ba/ZrO2 nanoparticles as efficient heterogeneous base catalyst for the synthesis of β-nitro alcohols and 2-amino 2-chromenes
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Zirconia nanoparticles were synthesized by precipitation, urea hydrolysis, amorphous citrate and combustion synthesis methods. The zirconia surface was subsequently modified by grafting Ba 2+ species. The Ba 2+ modified zirconia (Ba/ZrO 2) materials were characterized using XRD, Fourier analysis, UV-vis-DRS, FESEM and HRTEM techniques. XRD study indicated selective stabilization of the tetragonal phase of zirconia in the presence of Ba 2+ species. Fourier line profile analysis of the XRD peaks revealed that the average crystallite size of the zirconia nanoparticles is in the range of 5-15 nm. The surface area, basicity and barium content of the material depend strongly on the method of synthesis. The Ba/ZrO 2 catalyst prepared by urea hydrolysis method exhibited higher surface area and barium content compared to other samples. The catalytic activity of the Ba/ZrO 2 catalyst was evaluated for synthesis of β-nitro alcohols and 2-amino 2-chromenes. The β-nitro alcohols were synthesized by condensation of aryl aldehydes and nitromethane. Similarly, the 2-amino 2-chromenes were synthesized by condensation of arylaldehydes, α-naphthol and malononitrile. The Ba/ZrO 2 catalyst was found to be highly efficient for synthesis of both classes of compounds providing excellent yield and purity of the products. [Figure not available: see fulltext.]
- Pradhan, Sagnika,Swarnima, Kumari,Mishra
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p. 1119 - 1130
(2016/07/15)
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- Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure-activity relationships of 4-aryl group and 3-, 7-positions
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A series of 2-amino-4H-benzo[h]chromene and 2,7-diamino-4H-benzo[h]chromene derivatives were prepared as potential cytotoxic agents. The structures of the synthesised compounds were established on the basis of spectral data. The in-vitro cytotoxic activit
- El-Agrody, Ahmed M.,Abd El-Mawgoud, Heba K.,Fouda, Ahmed M.,Khattab, Essam S. A. E. H.
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p. 1279 - 1292
(2016/07/06)
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- Synthesis of pyran annulated heterocyclic scaffolds: A highly convenient protocol using dimethylamine
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A facile and rapid three-component synthesis of pharmaceutically diverse pyran annulated heterocycles has been developed via a one-pot condensation of aromatic aldehydes, malononitrile, and different enolizable C-H-activated acidic compounds in the presen
- Ramesh, Rathinam,Lalitha, Appaswami
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p. 8009 - 8017
(2015/02/19)
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- Nano silica-bonded aminoethylpiperazine: A highly efficient and reusable heterogeneous catalyst for the synthesis of 4H-chromene and 12H-chromeno[2,3-d]pyrimidine derivatives
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Abstract The reaction of nano silica with 3-chloropropyltrimethoxysilane followed by treatment with aminoethylpiperazine afforded nano silica-bonded aminoethylpiperazine (SB-APP). The structure of the synthesized SB-APP was characterized by FT-IR, TGA, BE
- Tajbakhsh, Mahmood,Kariminasab, Mohaddeseh,Alinezhad, Heshmatollah,Hosseinzadeh, Rahman,Rezaee, Parizad,Tajbakhsh, Mahgol,Gazvini, Helia Janatian,Amiri, Mohammadreza Azizi
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p. 1405 - 1414
(2015/06/22)
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- Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water
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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.
- Kiyani, Hamzeh,Ghorbani, Fatemeh
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p. 7847 - 7882
(2015/02/19)
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- Ultrasonic assisted synthesis of chromenes catalyzed by sodium carbonate in aqueous media
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A simple, efficient, and environmentally benign procedure for the synthesis of 2-amino-4Hchromene ring has been achieved by the three-component reaction of an aromatic aldehyde, malononitrile and diverse enolizable C-H activated compound under ultrasound
- Sabbaghan, Maryam,Sofalgar, Pegah
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p. 901 - 910
(2015/11/17)
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- Synthesis and Antimicrobial Activity of Mono, Bis and Tris 2-Amino-4HChromenes
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A clean and environmentally benign route to 2-amino-4H-chromenes has been developed using the reaction between various benzaldehydes, malononitrile and α-naphthol in the presence of 3,3′-(pentane-1,5-diyl)bis(1,2-dimethyl-1H-imidazol-3-ium) bromide. The p
- Nikpassand, Mohammad,Fekri, Leila Zare,Badri, Hanieh,Asadpour, Leila
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p. 685 - 692
(2016/03/25)
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- On water synthesis of pyran-chromenes via a multicomponent reactions catalyzed by fluorescent t-ZrO2 nanoparticles
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Here, we have demonstrated fluorescent tetragonal ZrO2 nanoparticle (t-ZrO2 NP) catalyzed green one-pot multicomponent protocol for the synthesis of diverse pyran-fused chromene analogues such as 2-aminochromene, dihydropyrano[3,2-c]
- Saha, Arijit,Payra, Soumen,Banerjee, Subhash
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p. 101664 - 101671
(2015/12/08)
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- N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: An efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media
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N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD) as a highly efficient and homogeneous catalyst was successfully applied for the synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivat
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Karimitabar, Fatemeh,Nikokar, Iraj,Moosavi-Zare, Ahmad Reza
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p. 71402 - 71412
(2015/09/08)
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- KG-60-piperazine as an efficient heterogeneous catalyst for three-component synthesis of 2-amino-2H-chromenes
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Abstract Silica-supported piperazine (KG-60-piperazine), as a mild and efficient basic catalyst, has played a role in the three-component reaction of some substituted benzaldehydes, malononitrile, and phenols, to yield the corresponding 2-amino-2H-chromen
- Golari, Neda,Rahimizadeh, Mohammad,Bakavoli, Mehdi,Rezaei-Seresht, Esmail
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p. 6023 - 6032
(2015/08/18)
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- Nano polypropylenimine dendrimer (DAB-PPI-G1): As a novel nano basic-polymer catalyst for one-pot synthesis of 2-amino-2-chromene derivatives
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The nano polypropylenimine dendrimer (DAB-PPI-G1) Lewis base catalyst was found to be a highly efficient and recoverable catalyst for the rapid and convenient synthesis of 2-amino-2-chromene derivatives through the three-component condensation of aromatic aldehydes, malononitrile or ethyl cyanoacetate and phenols under solvent-free conditions in excellent yields and short reaction times.
- Maleki, Behrooz,Sheikh, Safoora
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p. 42997 - 43005
(2015/05/27)
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- Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: Synthesis, biological evaluation and docking studies
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A series of 4-aryl/heteroaryl-4H-fused pyrans was synthesized via multicomponent reaction in a microwave synthesizer. All the pyrans were evaluated for in vitro xanthine oxidase inhibition. Structure-activity relationship was also established. Among the s
- Kaur, Ramandeep,Naaz, Fatima,Sharma, Sahil,Mehndiratta, Samir,Gupta, Manish Kumar,Bedi, Preet Mohinder Singh,Nepali, Kunal
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p. 3334 - 3349
(2015/08/03)
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