- Synthesis and X-ray structural investigations of 2-amino-7-methyl-4-(1- naphthyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile and 2-amino-4-(1- naphthyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile
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Synthesis and X-ray structural investigations have been carried out for the two title compounds C20H14N2O3 (4) and C23H14N2O3·C 2H3N (5). Compound 4 crystallizes in the monoclinic space group P21/n, with a = 7.0542(5), b = 8.822(1), c = 24.833(2) A, β = 94.30(4)°, V = 1541.0(4) A3, and Z = 4. Compound 5 crystallizes with an acetonitrile solvent molecule in the monoclinic space group P21/n, with a = 11.075(1), b = 7.854(1), c = 22.703(2) A, β = 90.67(1)°, V = 1974.5(3) A3, and Z = 4. In both molecules, the 4H-pyran ring adopts a flattened-boat conformation. The naphthalene substituent occupies a pseudo-axial position and the dihedral angle with the flat part of the pyran ring is equal to 94.6(3) in 4 and 76.8(3)° in 5. The mutual orientation of these fragments and the flatness of the heterocyclic rings lead to H...H intramolecular steric interactions: H4A...H18A 1.98 A in 4 and 2.11 A in 5. In the crystal of 4, intermolecular hydrogen bonds N-H...O and C-H...N link molecules into infinite tapes along the b axis. In the crystals of 5, intermolecular hydrogen bonds N-H...O and C-H...N link molecules into infinite layers parallel to the bc plane. In each case, the C-H...N interaction can be considered to be a weak hydrogen bond. The acetonitrile molecules link via intermolecular weak C-H...N hydrogen bonds to form infinite chains along the b axes.
- Nesterov, Vladimir N.,Wiedenfeld, David,Nesterova, Svitlana V.,Daniels, Lee M.
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- A simple, one pot synthesis of furo[3,2-c]chromenes and evaluation of antimicrobial activity
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Synthesis of a number of 2-cyano-4-oxo-3-phenyl-3,4-dihydro-2H-furo[3,2-c]chromene-2-carboxylate compounds (5) have been accomplished by a simple, multicomponent one pot reaction and evaluated for in vitro antimicrobial activity against different Gram-pos
- Kale, Ashok,Bingi, Chiranjeevi,Sripada, Sarada,Ganesh Kumar,Atmakur, Krishnaiah
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- One-pot synthesis of 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol
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Sodium citrate as a highly efficient catalyst is developed for the synthesis of functionalized 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocycles. This method involves a one-pot three-component reaction of aromatic aldehydes, malononitrile and 1,3
- Thongni, Aiborlang,Phanrang, Pynskhemborlang T.,Dutta, Arup,Nongkhlaw, Rishanlang
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supporting information
p. 43 - 62
(2021/11/09)
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- One‐pot and green synthesis 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and dihydropyrano[3,2-c]chromene derivatives by Fe3O4@SiO2-imine/phenoxy-Cu(II) as an efficient and reusable catalyst
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In the current study, magnetite-silica core–shell nanoparticles modified with Cu-salen complex (Fe3O4@SiO2-imine/phenoxy-Cu(II)) was utilized as a heterogeneous catalyst for the one-pot multicomponent synthesis of 1H-pyraz
- Azarifar, Davood,Ebrahimiasl, Hakimeh,Nesarvand, Milad
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p. 3629 - 3644
(2021/06/12)
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- Silica chemisorbed bis(hydrogensulphato)benzene (SiO2-BHSB) as a new, efficient, and recyclable catalyst for the synthesis of 5-oxopyrono[3,2-c]chromene scaffolds in water-based solvent
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The synthesis of silica chemisorbed bis(hydrogensulphato)benzene (SiO2-BHSB) as a new hybrid material was achieved by a sequence of three reactions. Structural features of the synthesized SiO2-BHSB were established by using analytica
- Kamble, Vinod T.,Waghmare, Amit S.,Murade, Vaishali D.,Kadam, Kailas R.
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p. 1038 - 1048
(2021/10/12)
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- Ni(II)-Schiff base/SBA-15: a nanostructure and reusable catalyst for one-pot three-component green synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives
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An efficient, rapid, and environmentally benign Ni(II)-Schiff base/SBA-15-catalyzed one-pot three-component cyclocondensation process was described via the reaction between malononitrile, 4-hydroxycoumarin, and various aldehydes in aqueous media for the s
- Noroozi Pesyan, Nader,Rezanejade Bardajee, Ghasem,Kashani, Elmira,Mohammadi, Marzieh,Batmani, Hana
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p. 347 - 367
(2019/09/13)
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- A Laccase Heterogeneous Magnetic Fibrous Silica-Based Biocatalyst for Green and One-Pot Cascade Synthesis of Chromene Derivatives
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Green cascade approaches, which utilize sustainable and recyclable heterogeneous biocatalysts, can be used in the catalysis of multicomponent organic reactions to synthesize biologically important substances. Three magnetic nanoparticles, iron (II, III) oxide, cobalt ferrite, and nickel ferrite, were prepared by co-precipitation and functionalized with fibrous silica (KCC-1), and characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). Laccase immobilized on CoFe2O4-KCC-1 was used as a heterogeneous biocatalyst for green and one-pot cascade synthesis of 2-amino-5-oxo-4-aryl-4H,5H-pyrano[3,2-c]chromene-3-carbonitriles. The reaction was performed in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a synthetic redox mediator. The optimum reaction conditions were found to be as immobilized laccase (100 mg, 95 U) and TEMPO (2 mol-%) in a 100 mm sodium citrate buffer (pH 4.5), 40 °C, and incubation time 17 h. About 80 % of initial activity of the immobilized laccase was retained after 15 independent runs.
- Mogharabi-Manzari, Mehdi,Ghahremani, Mohammad Hossein,Sedaghat, Tabassom,Shayan, Fatemeh,Faramarzi, Mohammad Ali
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p. 1741 - 1747
(2019/02/20)
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- Design, preparation and characterization of MoO3H-functionalized Fe3O4@SiO2 magnetic nanocatalyst and application for the one-pot multicomponent reactions
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Molybdic acid-functionalized silica-based Fe3O4 nanoparticles (Fe3O4@SiO2-MoO3H) are found to be a powerful and magnetically recyclable nanocatalyst. The morphology and structure of this na
- Kiani, Mahtab,Hendijani, Mehrnoosh,Mohammadipour, Mohammad,Ali, Zamanian
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p. 707 - 713
(2017/09/08)
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- Nano-Fe3O4@SiO2-supported boron sulfonic acid as a novel magnetically heterogeneous catalyst for the synthesis of pyrano coumarins
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In this study, a novel magnetically heterogeneous catalyst based on the immobilization of boron sulfonic acid onto Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2-BSA) is reported. Fe3Osub
- Farahi, Mahnaz,Karami, Bahador,Keshavarz, Raziyeh,Khosravian, Foroogh
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p. 46644 - 46650
(2017/10/13)
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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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- (CTA)3[SiW12]-Li+-MMT: A novel, efficient and simple nanocatalyst for facile and one-pot access to diverse and densely functionalized 2-amino-4H-chromene derivatives via an eco-friendly multicomponent reaction in water
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A simple, facile and highly efficient one-pot synthesis of a pharmaceutically interesting diverse kind of functionalized 2-amino-4H-chromene by a straightforward three-component reaction of an aromatic aldehyde, malononitrile (or ethyl cyanoacetate) and diverse enolizable C-H activated acidic compounds in the presence of a catalytic amount of (CTA)3[SiW12]-Li+-MMT is reported as a novel, environmentally friendly, reusable and promising nanocatalyst reaction in refluxing water. Based on the procedure, it was feasible to synthesize 2-amino-3-cyano-pyrano[3,2-c]chromen-5(4H)-one (4a-4y), 2-amino-3-cyano-pyrano[3,2-c]quinolin-5(4H)-one (6a-6s), 2-amino-3-cyano-7,8-dihydro-4H-chromen-5(6H)-one (8a-8u), 2-amino-3-cyano-pyrano[4,3-b]pyran-5(4H)-one (12a-12f), 2-amino-3-cyano-pyrano[3,2-c]pyridine-6(5H)-one (13a-13f), and 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-dione (14a-14f). The structure of the nanocatalyst was confirmed by various techniques such as IR, SEM, TGA-DTG, EDX, ICP and XRD analyses. In comparison to the conventional methods, the salient features of the present protocol are green reaction conditions, high quantitative yields, short reaction time, high atom economy, low cost, easy isolation of products, and no column chromatographic separation.
- Abbaspour-Gilandeh, Esmayeel,Aghaei-Hashjin, Mehraneh,Yahyazadeh, Asieh,Salemi, Hadi
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p. 55444 - 55462
(2016/07/06)
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- Silica-supported molybdic acid: Preparation, characterization, and its catalytic application in synthesis of pyranocoumarins
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Silica-supported molybdic acid was employed as novel, recyclable, and safe catalyst in a one-pot threecomponent condensation of aldehydes, malononitrile, and 4-hydroxycoumarin to produce new and known pyr- ano[2,3-c]chromenes as potent biologically active
- Karami, Bahador,Kiani, Mahtab
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p. 1117 - 1124
(2016/09/09)
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- Synthesis and characterization of novel nanosilica molybdic acid and its first catalytic application in the synthesis of new and known pyranocoumarins
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Nanosilica molybdic acid (nano-SMA) was prepared and employed as a novel, recyclable and safe catalyst for the one-pot, three-component condensation of 4-hydroxycoumarin with aldehydes and malononitrile to produce new and known pyrano[2,3-c]chromenes as p
- Karami, Bahador,Kiani, Mahtab,Hosseini, S. Jafar,Bahrami, Mehrangiz
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p. 8576 - 8581
(2015/11/10)
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- A green synthesis of substituted coumarins using nano graphene oxide as recyclable catalyst
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One-pot synthesis of some pyranocoumarins and biscoumarins using graphene oxide nanosheets as efficient catalyst has been investigated. The green methods offer appealing attributes such as excellent yields, short reactions times, use of a safe and recycla
- Khodabakhshi, Saeed,Marahel, Farzaneh,Rashidi, Alimorad,Abbasabadi, Masoud Khaleghi
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p. 389 - 392
(2015/05/27)
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- Sodium tungstate: The first application as non-oxidative catalyst in organic synthesis
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A convenient synthesis of some pyranocoumarins was described via a one-pot, three-component reaction of 4-hydroxyxoumarin, malononitrile and different aromatic aldehydes in the presence of sodium tungstate. This is the first application of sodium tungstat
- Khodabakhshi, Saeed,Baghernejad, Mojtaba
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p. 521 - 524
(2014/05/20)
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- Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins
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Titanium dioxide nanowires were employed as novel, recyclable and safe catalysts in a one-pot three-component condensation of aldehydes, malononitrile, and 4-hydroxycoumarin to produce new and known pyrano[2,3-c]chromenes as potent biologically active com
- Khodabakhshi, Saeed,Karami, Bahador,Eskandari, Khalil,Hoseini, Seyed Jafar
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- A new application of mohr's salt as a cheap and powerful catalyst for synthesis of novel pyranocoumarins
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A new application of Mohr's salt (ammonium iron (II) sulfate hexahydrate) has been found in an organic reaction in which the Knoevenagel condensation, Michael addition, and intermolecular cyclization of 4-hydroxyxoumarin, malononitrile and aromatic aldehy
- Karami, Bahador,Khodabakhshi, Saeed,Eskandari, Khalil
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p. 105 - 110
(2013/07/26)
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- Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions
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A simple, efficient and ecofriendly procedure has been developed using tetrabutylammonium bromide as catalyst for the synthesis of biscoumarin and dihydropyrano[c]chromene derivatives in water and solvent-free neat conditions. The present methodology offe
- Khurana, Jitender M.,Kumar, Sanjay
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experimental part
p. 4125 - 4127
(2009/11/30)
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- Synthesis and reactions of some new 4H-pyrano[3,2-c]benzopyran-5-one derivatives and their potential biological activities
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Several new 4H-pyrano[3,2-c]benzopyran-5-ones (6a-g and 10) which exhibited antibacterial and fungicidal activity, have been synthesized via a one flask multicomponent condensation of aldehydes with malononitrile and 4-hydroxycoumarin. The reactions of 6a
- Shaker
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p. 148 - 151
(2007/10/03)
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