- 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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- 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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- 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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- Ultrasound irradiation for the green synthesis of chromenes using L-arginine-functionalized magnetic nanoparticles as a recyclable organocatalyst
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A practical, convenient, and cheap methodology is developed for the synthesis of a series of chromene derivatives via cyclocondensation of α- or β-naphthol, malononitrile and aromatic aldehydes, in the presence of l-arginine-immobilized magnetic nanoparti
- Azizi, Kobra,Karimi, Meghdad,Shaterian, Hamid Reza,Heydari, Akbar
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- New pyrano-1,2,3-triazolopyrimidinone derivatives as anticholinesterase and antibacterial agents: Design, microwave-assisted synthesis and molecular docking study
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This work describes an effective microwave-assisted synthesis of new hybrid regioisomeric molecules N-linked-1,2,3-triazole along with pyranopyrimidinone moiety under copper(I) catalyst, and the evaluation of their anticholinesterase and antibacterial act
- Al-Ghamdi, Youssef O.,Almalki, Sami G.,Alqurashi, Yaser E.,Ben Jannet, Hichem,Cherif, Maher,Horchani, Mabrouk,Romdhane, Anis
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- Novel Metal Oxide of CuO-ZnO Nanocatalyst Efficiently Catalyzed the Synthesis of 2-Amino-4 H -chromenes in Water
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Novel metal oxide of CuO-ZnO nanocatalyst was prepared by a coprecipitation method and characterized by x-ray diffusion, Brunauer-Emmett-Teller surface area, scanning electron microscopy, transmission electron microscopy, and energy dispersive spectroscop
- Albadi, Jalal,Alihoseinzadeh, Amir,Mansournezhad, Azam,Kaveiani, Leila
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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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- 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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- Novel ferrocene-based ionic liquid supported on silica nanoparticles as efficient catalyst for synthesis of naphthopyran derivatives
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We report synthesis of silica nanospheres containing ferrocene-tagged imidazolium acetate (SiO2@Im-Fc[OAc]) as efficient heterogeneous nanocatalyst for synthesis of naphthopyran derivatives under solvent-free conditions, based on modification o
- Teimuri-Mofrad, Reza,Gholamhosseini-Nazari, Mahdi,Payami, Elmira,Esmati, Somayeh
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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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- 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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- 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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- Ferrocene-tagged ionic liquid stabilized on silica-coated magnetic nanoparticles: Efficient catalyst for the synthesis of 2-amino-3-cyano-4H-pyran derivatives under solvent-free conditions
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An advanced novel magnetic ionic liquid based on imidazolium tagged with ferrocene, a supported ionic liquid, is introduced as a recyclable heterogeneous catalyst. Catalytic activity of the novel nanocatalyst was investigated in one-pot three-component re
- Teimuri-Mofrad, Reza,Gholamhosseini-Nazari, Mahdi,Payami, Elmira,Esmati, Somayeh
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- Polystyrene-supported 1-methylimidazolium tetrachloro ferrate: Synthesis, characterization, and application as an efficient and reusable heterogeneous catalyst for one-pot synthesis of 4H-chromene derivatives in aqueous media
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Polystyrene-supported 1-methylimidazolium tetrachloroferrate (PS[mim][FeCl4]) was prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM) and energy dispersive X-ray analysis (EDX). The
- Taheri, Narges,Fallah-Mehrjardi, Mehdi,Sayyahi, Soheil
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- Convenient method for synthesis of substituted 2-amino-2-chromenes
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Some substituted 2-amino-2-chromenes were synthesized by the reaction of arylidenemalononitriles with 1-naphthol or 2-naphthol in the presence of sodium hydroxide as catalyst under solvent-free condition. Copyright Taylor & Francis Group, LLC.
- Zhang, Ai-Qin,Zhang, Ming,Chen, Huan-Huan,Chen, Jun,Chen, Hai-Yan
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- Aqua mediated synthesis of substituted 2-amino-4H-chromenes catalyzed by green and reusable Preyssler heteropolyacid
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A simple, clean and environmentally benign route to the synthesis of 2-amino-4H-chromenes is described using Preyssler type heteropolyacid, H14[NaP5W30O110], as a green and reusable catalyst in water. The produc
- Heravi, Majid M.,Bakhtiari, Khadijeh,Zadsirjan, Vahideh,Bamoharram, Fatemeh F.,Heravi, Omid M.
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- Design and synthesis of new naphtho[2,1-b]pyrano [2,3-d]pyrimidinones under classical and microwave conditions
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A fast and efficient method for the synthesis of naphthopyranopyrimidinones derivatives in excellent yields was developed through cyclocondensation reaction between previously prepared pyrimidinic hydrazides and some electrophilic species such as 2,4-pentanedione, 2,5-hexanedione, cyclic anhydrides, and phenylthioisocyanate under microwave irradiation. Compared to the conventional methods applied, it was found that better yields and shorter reaction times were achieved using microwave-assisted synthesis. Structures of all synthesized compounds were established on the basis of spectroscopic methods including 1 H NMR,13 C NMR, and HRMS-ES.
- Cherif, Maher,Debbabi, Mariem,Chortani, Sarra,Romdhane, Anis,Ben Jannet, Hichem
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- Synthesis and Biological Assessment of Racemic Benzochromenopyrimidinimines as Antioxidant, Cholinesterase, and Aβ1?42Aggregation Inhibitors for Alzheimer's Disease Therapy
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Given the complex nature of Alzheimer′s disease (AD), compounds that are able to simultaneously address two or more AD-associated targets show greater promise for development into drugs for AD therapy. Herein we report an efficient two-step synthesis and biological evaluation of new racemic benzochromene derivatives as antioxidants, inhibitors of cholinesterase and β-amyloid (Aβ1?42) aggregation. Based on the results of the primary screening, we identified 15-(3-methoxyphenyl)-9,11,12,15-tetrahydro-10H,14H-benzo[5,6]chromeno[2,3-d]pyrido[1,2-a]pyrimidin-14-imine (3 e) and 16-(3-methoxyphenyl)-9,10,11,12,13,16-hexahydro-15H-benzo[5′,6′]chromeno[2′,3′:4,5]pyrimido[1,2-a]azepin-15-imine (3 f) as new potential multitarget-directed ligands for AD therapy. Further in-depth biological analysis showed that compound 3 f is a good human acetylcholinesterase inhibitor [IC50=(0.36±0.02) μm], has strong antioxidant activity (3.61 μmol Trolox equivalents), and moderate Aβ1?42antiaggregating power (40.3 %).
- Dgachi, Youssef,Ismaili, Lhassane,Knez, Damijan,Benchekroun, Mohamed,Martin, Hélène,Sza?aj, Natalia,Wehle, Sarah,Bautista-Aguilera, Oscar M.,Luzet, Vincent,Bonnet, Alexandre,Malawska, Barbara,Gobec, Stanislav,Chioua, Mourad,Decker, Michael,Chabchoub, Fakher,Marco-Contelles, José
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- Synthesis of a novel piperidine-functionalized poly(ethylene glycol) bridged dicationic ionic liquid and its application in one-pot synthesis of substituted 2-amino-2-chromenes and 3,4-dihydropyrano[3,2-c]chromenes in aqueous media
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A novel piperidine-functionalized poly(ethylene glycol) bridged dicationic ionic liquid was prepared and identified. It was used as a recyclable catalyst for the synthesis of substituted 2-amino-2-chromenes and 3,4-dihydropyrano[3,2- c]chromenes with exce
- Wang, Yinglei,Luo, Jun,Xing, Tantan,Liu, Zuliang
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- Ultrasonic-assisted preparation of Co3O4 and Eu-doped Co3O4 nanocatalysts and their application for solvent-free synthesis of 2-amino-4H-benzochromenes under microwave irradiation
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Co3O4 and Eu-doped Co3O4 nanocatalysts were synthesized through an ultrasonic-assisted solvothermal method and were characterized with X-ray diffraction (XRD), Fourier transform infrared (FT-IR), energy-dispersi
- Kafi-Ahmadi, Leila,Poursattar Marjani, Ahmad,Nozad, Ehsan
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- Synthesis, characterization, anti-proliferative properties and DNA binding of benzochromene derivatives: Increased Bax/Bcl-2 ratio and caspase-dependent apoptosis in colorectal cancer cell line
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3-Amino-1-aryl-1H-benzo[f]chromene-2-carbonitrile derivatives were synthesized from three-component reaction of arylaldehyde, malononitrile and 2-naphthol in the presence of 1, 4-bis(4-ferrocenylbutyl)piperazine as a new catalyst. Cytotoxic potencies of t
- Ahagh, Mina Hanifeh,Dehghan, Gholamreza,Mehdipour, Maryam,Teimuri-Mofrad, Reza,Payami, Elmira,Sheibani, Nader,Ghaffari, Maryam,Asadi, Milad
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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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- Photochemical synthesis of benzo[: F] chromene
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The one-pot photocatalytic synthesis of benzo[f]chromene was performed at room temperature by the addition of benzyl alcohol, malononitrile and β-naphthol in contact with an illuminated nano-SnO2/TiO2 composite. This study illustrated the potential of photochemical synthesis of benzo[f]chromene. A simple procedure was proposed for the synthesis of a nano-SnO2/TiO2 composite using the sol-gel method by hydrolysis of tin(iv) chloride and titanium(iv) chloride at room temperature in the presence of polyethylene glycol 200, diethanolamine, and distilled water. Scanning electron microscopy (SEM), X-ray diffraction (XRD), and FT-IR were employed to characterize the proposed photocatalyst.
- Akbari
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- A novel and efficient catalyst to one-pot synthesis of 2-amino-4H-chromenes by methanesulfonic acid
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Methanesulfonic acid efficiently catalyzes the one-pot, three component reaction of an aromatic aldehyde, malonitrile and α or β-naphthol to yield 2-amino-4H-chromenes in very good yields.
- Heravi, Majid M.,Baghernejad, Bita,Oskooie, Hossein A.
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- Piperazine-functionalized nickel ferrite nanoparticles as efficient and reusable catalysts for the solvent-free synthesis of 2-amino-4H-chromenes
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Piperazine-functionalized nickel ferrite (NiFe2O4) nanoparticles were synthesized as recoverable heterogeneous base catalysts using a routine method. The synthesized materials were characterized using various spectroscopic techniques
- Pourhasan, Bahram,Mohammadi-Nejad, Ahmad
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- Thiourea dioxide catalyzed multi-component coupling reaction for the one step synthesis of naphthopyran derivatives
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An aqueous solution of thiourea dioxide was used to catalyze a one-pot three-component coupling reaction of an aromatic aldehyde, malononitrile, and α- or β-naphthol for the synthesis of various naphthopyran derivatives in excellent yields. At the end of
- Verma, Sanny,Jain, Suman L.
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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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- 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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- 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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- Solvent-free synthesis of compounds containing chromene core catalyzed by novel Br?nsted acidic ionic liquids-ClO4
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A series of novel sulfonic acid-functionalized Br?nsted acidic ionic liquids (BAILs) with perchlorate counter anion are introduced. These ionic liquid catalysts were prepared through simple and eco-friendly procedures in high yields. Various analytical te
- Taib, Layla A.,Keshavarz, Mosadegh,Parhami, Abolfath
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p. 1128 - 1137
(2021/02/03)
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- Synthesis of 2-amino-3-cyano-4H-pyran derivatives using GO-Fc@Fe3O4 nanohybrid as a novel recyclable heterogeneous nanocatalyst and preparation of tacrine-naphthopyran hybrids as AChE inhibitors
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Abstract: GO-Fc@Fe3O4 nanohybrid as a powerful and reusable nanocatalyst was synthesized. The graphene oxide (GO) sheets with meta-chloroperoxybenzoic acid (mCPBA) were treatment, afterward were chemically modified with 4-Fc derivati
- Mozaffarnia, Sakineh,Teimuri-Mofrad, Reza,Rashidi, Mohammad-Reza
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p. 1455 - 1470
(2021/01/05)
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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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- Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4: H -chromenes
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Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si{1H} and 13C{1H} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid-base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C-H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles.
- Jahanshahi, Roya,Khazaee, Asma,Sansano, José Miguel,Skibsted, J?rgen,Sobhani, Sara
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p. 4604 - 4616
(2020/08/10)
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- Cytotoxic activity and DNA binding property of new aminopyrimidine derivatives
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Background: Chromene and anilinopyrimidine heterocyclics are attractive anticancer compounds that have inspired many researchers to design novel derivatives bearing improved an-ticancer activity. Method: A series of pyrimidine-fused benzo[f]chromene deriv
- Akrami, Hamidreza,Emami, Saeed,Firuzi, Omidreza,Foroumadi, Alireza,Hekmat, Azadeh,Jeivad, Fereshteh,Khoobi, Mehdi,Miri, Ramin,Mirjalili, Bibi Fatemeh,Moghimi, Setareh,Pirali-Hamedani, Morteza,Sab-Oury, Ali Akbar,Sabzevari, Omid
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p. 638 - 652
(2020/04/17)
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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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- Ultrasonic accelerated efficient synthesis of aminobenzochromenes using Ag2Cr2O7 nanoparticles as a reusable heterogeneous catalyst
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Ag2Cr2O7 nanoparticles were found to be an exceedingly effective catalyst for the mild and green synthesis of aminobenzochromenes. The reaction was performed under ultrasonic irradiation as an innocuous tool and in water a
- Ebrahimi, Mitra,Abdolmohammadi, Shahrzad,Kia-Kojoori, Reza
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p. 1875 - 1881
(2020/02/18)
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- Nickel oxide-catalyzed synthesis of 4-amino-2H-chromenes: ITS application in antimicrobial studies and towards protein docking
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This work involves the synthesis of densely functionalized 2-amino-4H-chromenes by domino Knoevenagel-Michael-cyclization reaction of aromatic aldehydes, β-naphthol and malononitrile in the presence of a catalytic amount of a heterogeneous and reusable gr
- Neela,Clarina,Rama
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p. 1049 - 1056
(2019/04/05)
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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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- 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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- 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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- 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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- An affordable DABCO-based ionic liquid efficiency in the synthesis of 3-amino-1-aryl-1H-benzo[f] chromene-2-carbonitrile, 1-(benzothiazolylamino)phenylmethyl-2-naphthol, and 1-(benzoimidazolylamino)phenylmethyl-2-naphthol derivatives
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In this study, [H2-DABCO][HSO4]2 is applied as an acidic ionic liquid to exclude some disadvantages of former methods reported for the synthesis of 3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitrile, 1-(benzothiazolylamino)
- Nabinia, Nazanin,Shirini, Farhad,Tajik, Hassan,Mashhadinezhad, Maryam,Langarudi, Mohaddeseh Safarpoor Nikoo
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p. 2147 - 2157
(2018/08/03)
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- A green method synthesis and antimicrobial activity of 2-amino-4H-chromene derivatives
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Agro-waste stuff ash extracted solution have been emerging in recent practicing green reaction catalysis in organic synthesis. The derived media have been demonstrated in reactions like Sonogashira, Dakin, Henry, Suzuki-Miyaura, amide bond formation. Trad
- Kantharaju,Khatavi, Santosh Y.
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p. 1496 - 1502
(2018/06/12)
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- Glucose-coated superparamagnetic nanoparticle-catalysed pyrazole synthesis in water
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A green, benign, heterogeneous, superparamagnetic catalyst (Glu.@Fe3O4) was synthesized and characterized using Fourier transform infrared spectroscopy, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy and vibrating sample magnetometry. The prepared catalyst was used to achieve a high-efficiency, low-cost, eco-friendly and easy-to-handle protocol for synthesizing substituted pyrazole derivatives from aldehydes, malononitrile and phenylhydrazine. The catalyst was also used in chromene synthesis. Glucose coated on magnetic nanoparticles provided excellent catalytic activity. The catalyst could be recycled for up to four runs without significant loss in catalytic activity.
- Esfandiary, Naghmeh,Nakisa, Athar,Azizi, Kobra,Azarnia, Jamshid,Radfar, Iman,Heydari, Akbar
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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 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, 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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- Synthesis of functionalized chromene and spirochromenes using L-proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
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An efficient and recyclable homogeneous catalyst is developed using commercially cheap L-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, L-proline and melamine (3:1 ratio; 3 mol% on total weight) was found to be best catalyst to give the desired products with excellent yields (up to 99%) in very short times (1–15 min) at room temperature in DMSO as solvent. The catalyst was recovered by adding EtOAc and reused up to 5 cycles without losing the catalytic activity.
- Nagaraju, Sakkani,Paplal, Banoth,Sathish, Kota,Giri, Santanab,Kashinath, Dhurke
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supporting information
p. 4200 - 4204
(2017/10/06)
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- Synthesis, antifungal activity and docking study of 2-amino-4H-benzochromene-3-carbonitrile derivatives
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Pathogenic fungi are associated with diseases ranging from simple dermatosis to life-threatening infections, particularly in immunocompromised patients. During the past two decades, resistance to established antifungal drugs has increased dramatically and
- Mirjalili, BiBi Fatemeh,Zamani, Leila,Zomorodian, Kamiar,Khabnadideh, Soghra,Haghighijoo, Zahra,Malakotikhah, Zahra,Ayatollahi Mousavi, Seyyed Amin,Khojasteh, Shaghayegh
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p. 102 - 108
(2017/01/12)
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- Straightforward and solvent-free synthesis of 2-amino-4H-chromenes in the presence of a choline-based magnetic ionic liquid as catalyst
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Choline tetrachloroferrate with a magnetic response property is applied in multicomponent one-pot synthesis of 2-amino-4H-chromenes as effective catalyst. The catalyst is characterized by the UV–Vis and Raman spectroscopies and by the electrospray ionizat
- Khodajoo,Sayyahi,Saghanezhad
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p. 1177 - 1181
(2016/07/06)
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- Triazine-Based Porous Organic Polymer with Good CO2 Gas Adsorption Properties and an Efficient Organocatalyst for the One-Pot Multicomponent Condensation Reaction
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A new porous organic polymer PDVBTT-1 (poly-divinylbenzene-co-triallyloxytriazine) has been synthesized through radical co-polymerization utilizing two monomers, that is, divinylbenzene and 2,4,6-triallyloxy-1,3,5-triazine in the presence of AIBN (azobisi
- Bhanja, Piyali,Chatterjee, Sauvik,Bhaumik, Asim
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p. 3089 - 3098
(2016/10/11)
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- Ion-pair immobilization of l-prolinate anion onto cationic polymer support and a study of its catalytic activity as an efficient heterogeneous catalyst for the synthesis of 2-amino-4H-chromene derivatives
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A novel clean and simple technique for the heterogenization of l-proline organocatalyst has been introduced. This procedure is based on non-covalent immobilization of l-proline on the surface of an anion-exchange resin amberlite IRA900OH (AmbIRA900OH) as
- Keshavarz, Mosadegh,Iravani, Nasir,Ahmadi Azqhandi, Mohammad Hossein,Nazari, Simin
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p. 4591 - 4604
(2016/07/06)
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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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- 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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