- One-pot synthesis of spirooxindole derivatives catalyzed by lipase in the presence of water
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A facile one-pot synthesis route to spirooxindole derivatives was developed by combining the three types of catalytic activities of lipase from porcine pancreas (PPL) in the presence of water, i.e., the Knoevengel condensation, Michael addition and cyclization. PPL showed excellent catalytic activity and have a good adaptability to different substrates in the reaction. All the reactions go smoothly and provide spirooxindole derivatives with high yield under the mild conditions. This lipase-catalyzed multistep conversion method has provided a new strategy to synthesize spirooxindole derivatives and expanded the application of biocatalysts.
- Chai, She-Jie,Lai, Yi-Feng,Xu, Jiang-Cheng,Zheng, Hui,Zhu, Qing,Zhang, Peng-Fei
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- Magnetic calcined oyster shell functionalized with taurine immobilized on β-cyclodextrin (Fe3O4/COS@β-CD-SO3H NPs) as green and magnetically reusable nanocatalyst for efficient and rapid synthesis of spirooxindoles
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Abstract: Magnetic calcined oyster shell functionalized with taurine immobilized on β-cyclodextrin (Fe3O4/COS@β-CD-SO3H NPs) was prepared as a new stable, long-lived, highly efficient, and exceptional reusable magnetic nan
- Mohammadian, Narges,Akhlaghinia, Batool
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p. 4737 - 4756
(2019/06/04)
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- A simple and one-pot synthesis of tetrahydrobenzo[b]pyrans and spirooxindoles catalyzed by H-Fe3 O4 @DA-SO3 h as an efficient, light and reusable nanocatalyst
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Aim and Objective: One of the principles of green chemistry is using inexpensive reagents and catalysts to design green route for synthesis of organic compounds. Recently magnetic nanoparticles have provided a considerable merits. In this study, hollow Fe
- Mirhosseyni, Marzie Sadat,Nemati, Firouzeh,Elhampour, Ali
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p. 487 - 494
(2018/12/13)
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- Caspian Isinglass, a versatile and sustainable biocatalyst for domino synthesis of spirooxindoles and spiroacenaphthylenes in water
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Abstract: Isinglass, derived from swim bladders of Caspian Sea fish and consisting predominantly of protein collagen, was found to be an effective, easily accessible heterogeneous biocatalyst for the synthesis of biologically important functionalized spir
- Javanshir, Shahrzad,Saghiran Pourshiri, Nassim,Dolatkhah, Zahra,Farhadnia, Mohammad
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p. 703 - 710
(2017/03/17)
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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 of spirochromene derivatives catalyzed by Mn(bpyo)2/MCM-41 in water
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A three-component one-pot synthesis of spirochromene derivatives by condensing cyclic 1,3-diketones, isatin or acenaphthenequinone, and malononitrile using a catalytic amount of Mn(bpyo)2/MCM-41 in refluxing water is reported.
- Daraie, Mansoureh,Beheshtiha, Yahya S.,Heravi, Majid M.
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p. 191 - 198
(2015/03/03)
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- Protic guanidinium ionic liquid as a green and highly efficient catalyst for the synthesis of functionalized spirochromenes under solvent-free conditions
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A simple and efficient method for the synthesis of functionalized spirochromenes is explained using protic guanidinium ionic liquid as a catalyst under solvent-free conditions at room temperature. This procedure is simple, clean, and excellent yields are
- Baghbanian, Seyed Meysam,Tajbakhsh, Mahmood,Farhang, Maryam
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p. 1160 - 1164
(2015/02/18)
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- Novel and thermally stable ionic liquid (TBA acetate) for domino reaction: Synthesis of spirooxindoles via new mechanistic way
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A simple, efficient and environmentally benign method for the one-pot, three component synthesis of spirooxindoles under task-specific novel ionic liquid Tetrabutylammonium acetate (TBA acetate) mediated and catalyzed conditions is described involving isa
- Riyaz, Sd,Indrasena,Naidu,Dubey
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p. 1442 - 1447
(2014/12/11)
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- Greener synthesis of spirooxindole in deep eutectic solvent
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A simple and efficient synthesis of spirooxindole derivatives by one-pot, three-component reaction of isatins, malononitrile and different nucleophiles under catalyst-free condition in deep eutectic solvent is reported. A series of biological importance, spirooxindole derivatives were synthesized via a multicomponent reaction of isatin, or acenaphthoquinone, and malononitrile or cyanoacetic ester with 1,3-dicarbonyl compounds, naphtol and 4-hydroxycumarin in biodegradable choline chloride based deep eutectic solvent in good yields (50-95%). This green procedure has the advantages of higher yields, shorter reaction times, environmental friendliness, and easy work-up.
- Azizi, Najmedin,Dezfooli, Sahar,Mahmoudi Hashemi, Mohammad
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- Carbon-SO3H: A novel and recyclable solid acid catalyst for the synthesis of spiro[4H-pyran-3,3′-oxindoles]
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A bioglycerol derived carbon-sulfonic acid is found to catalyze efficiently the three-component one-pot condensation of isatin, malononitrile, and 1,3-dicarbonyls to afford a wide range of spiro[4H-pyran-3,3′-oxindole] derivatives in good yields and selec
- Maheshwar Rao,Reddy, G. Niranjan,Reddy, T. Vijaikumar,Devi, B.L.A. Prabhavathi,Prasad,Yadav,Reddy, B.V. Subba
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p. 2466 - 2471
(2013/06/26)
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- One-pot three-component synthesis of spirooxindoles catalyzed by hexamethylenetetramine in water
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A simple, convenient, and multicomponent strategy for synthesis of spirooxindole derivatives has been developed. This strategy provides a rapid access to construct a diversity-oriented library of spirooxindoles by using three simple and readily available isatin, malononitrile or cyanoacetic ester, and 1,3-dicarbonyl compound catalyzed by hexamethylenetetramine in water.
- Wang, Guo-Dong,Zhang, Xiao-Nan,Zhang, Zhan-Hui
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- Ethylenediammonium diformate (EDDF) in PEG600: An efficient ambiphilic novel catalytic system for the one-pot synthesis of 4H-pyrans via Knoevenagel condensation
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A novel ethylenediammonium diformate-polyethylene glycol (EDDF-PEG 600) system was developed as a catalyst for the Knoevenagel condensation and Knoevenagel initiated three-component one-pot synthesis of 4H-pyrans at room temperature with high yields and in short reaction times. Further, the EDDF-PEG600 catalytic system was recycled six times without any appreciable loss in its activity and hence can be termed as a green, environmentally benign catalytic system. A plausible mechanism depicting the ambiphilic nature of EDDF (catalyst) and PEG (promoting medium) acting in synergy has been proposed. The Royal Society of Chemistry.
- Thakur, Anuj,Tripathi, Mohit,Rajesh, U. Chinna,Rawat, Diwan S.
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p. 18142 - 18148
(2013/10/01)
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- A clean and expedient synthesis of spirooxindoles in aqueous media catalyzed over nanocrystalline MgO
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An efficient and eco-friendly method for the synthesis of spirooxindoles with fused tetrahydrochromenes has been demonstrated using basic nanocrystalline MgO catalyst in aqueous condition. The method has been applied for the synthesis of a range of compou
- Karmakar, Bikash,Nayak, Anupam,Banerji, Julie
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p. 5004 - 5007
(2012/11/07)
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- Triphenylphosphine catalyzed, one-pot, multicomponent synthesis of spirooxindoles
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Multicomponent reaction involving isatin (1), malononitrile (2), and dimedone (3), in the presence of triphenylphosphine as an efficient catalyst in the eco-friendly solvent ethanol, results in the formation of spirooxindole derivatives 4 i.e 2-Amino-5-oxo-7,7-dimethyl spiro[(4H)-5,6,7,8- tetrahydrochromene-4,3-(3H)-indol]-(10H)-2-onecarbonitrile. The reaction proceeds smoothly under mild conditions and the products are obtained in good to excellent yields. This method is applicable to a variety of isatin derivatives.
- Riyaz, Syed,Naidu,Dubey, Pramod K.
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experimental part
p. 101 - 105
(2012/08/08)
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- Gold(III) chloride (HAuCl4·3H2O) in PEG: A new and efficient catalytic system for the synthesis of functionalized spirochromenes
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Gold(III) chloride (HAuCl4·3H2O) in PEG 400 was found to be an efficient catalytic system for the synthesis of biologically important functionalized spirochromene derivatives via one-pot three-component reaction of isatins/acenaphthoquinone, active methylene compounds and cyclic 1,3-diketones/4-hydroxycoumarin. A new catalytic system, recyclability of reaction medium, little reaction times and excellent yields with easy workup render this protocol more attractive and economically viable.
- Kidwai, Mazaahir,Jahan, Anwar,Mishra, Neeraj Kumar
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experimental part
p. 35 - 43
(2012/07/02)
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- Ambient synthesis of spiro[4H-pyran-oxindole] derivatives under [BMIm]BF4 catalysis
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A simple and efficient one-pot approach for assembling some fused spiro[4H-pyran-oxindole] heterocycles by means of three-component reactions between isatins, malononitrile or ethyl cyano-acetate, and 1,3-dicarbonyl compounds is reported. The combinatoria
- Rad-Moghadam, Kurosh,Youseftabar-Miri, Leila
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experimental part
p. 5693 - 5699
(2011/08/22)
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- Efficient one-pot synthesis of spirooxindole derivatives catalyzed by L-proline in aqueous medium
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An efficient one-pot synthesis of spirooxindole derivatives by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of L-proline is reported. This new protocol has the advantages of e
- Li, Yuling,Chen, Hui,Shi, Chunling,Shi, Daqing,Ji, Shunjun
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supporting information; experimental part
p. 231 - 237
(2010/08/20)
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- Ammonium salt catalyzed multicomponent transformation: simple route to functionalized spirochromenes and spiroacridines
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The combination of isatin or acenaphthoquinone, an activated methylene reagent, and 1,3-dicarbonyl compounds in the presence of catalytic ammonium chloride was found to be a suitable and efficient method for the synthesis of the biologically important spirooxindoles.
- Dabiri, Minoo,Bahramnejad, Mahboobeh,Baghbanzadeh, Mostafa
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experimental part
p. 9443 - 9447
(2010/01/06)
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- Synthesis of fused 2′-amino-3′-R-spiro-[indole-3,4′- pyran]-2(1H)-ones
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An efficient one-pot procedure has been proposed for the synthesis of fused 2′-amino-3′-R-spiro-[indole-3,4′-pyran]-2(1H)-ones via base-catalyzed three-component condensation of isatins with the corresponding nitriles and 1,3-diketones.
- Shemchuk,Chernykh,Red'kin
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experimental part
p. 1789 - 1794
(2009/09/06)
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