- Imino isatin derivatives; synthesis, in silico molecular dynamic study over monoamine oxidase B, ADME prediction, and in vitro cytotoxicity evaluation
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The monoamine oxidase B (MAO-B) depicts an attractive drug target for the development of neuro protective agents toward the treatment of neurodegenerative diseases. The current study involved synthesis, in silico and cytotoxic evaluation of N1-alkylated-5-substituted 3-imino isatin derivatives with the proposed MAO-B inhibitory activities. The In silico molecular modeling investigation was performed through the induced fit docking, molecular mechanics-generalized born surface area, and molecular dynamic method in order to uncover the binding mode interaction and their proposed impact on the active site environment and flexibility. The synthesized compounds were characterized by spectroscopic methods. Compound 3-Imino-1-pentyl indolin-2-one (3h) with the highest free binding energy adopts an extended conformation spanning from the flavin ring location to the entrance of the substrate cavity. In this way, Ile199 adopts the “open” conformation so the two separate cavities of MAO-B active site fused and formed a single-space, which abled the compound extending to the MAO-B entrance cavity space. From consideration of the data presented in this paper, we reveal that longer N1-alkylated-3-imino isatin derivative could be proposed as inhibitor that would occupy both cavities of the MAO-B active site. Furthermore, the mentioned derivatives provided acceptable drug profiling based on in silico ADME calculation and MTT cytotoxicity test evaluation.
- Ahmadi, Samaneh,Azizian, Homa,Azizian, Javad
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- Nukleophile Reaktionen an 2-Phenylindolenin-3-onen
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Nucleophilic reagents such as 4-nitrophenylhydrazine, malonic acid derivatives, and hydrogen peroxide react with 2-phenylindolenin-3-ones giving, in the first step, addition products to the N=C(2) bond.This addition can be reversible, but in most cases ne
- Adam, Jean-Marie,Winkler, Tammo
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- An efficient procedure for the synthesis of spiro [3H-indole-3,4' (1'H) pyrano [2,3-C] pyrrole]-5'-carbonitriles using solid inorganic supports and microwave activation
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Microwave irradiation accelerates the Michael condensation of 3- dicyanomethylene-2H-indole-2-one with 2-pyrrolidone/N-methyl-2-pyrrolidone (i) adsorbed on neutral alumina in 'dry media' (ii) using absolute ethanol as energy transfer medium. 3-Dicyanomethylene-2H-indol-2-one was synthesized under microwave irradiation using indole-2,3-dione and malononitrile. The results were compared with those obtained following the classical method. The advantages obtained by the use of microwave irradiation are demonstrated.
- Dandia, Anshu,Taneja, Harshita,Gupta, Rajive,Paul, Satya
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- An environmentally benign approach for the synthesis of 3,3′-pyrrolidonyl spirooxindole derivatives via a cascade Knoevenagel-Michael-cyclization multicomponent reaction
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A series of 3,3′-pyrrolidonyl spirooxindole derivatives have been synthesized in good yields from the cascade Knoevenagel-Michael-cyclization multicomponent reaction of isatin, malononitrile and α-isothiocyanato imide in the presence of a catalytic amount
- Yu, Chengbin,Lyu, Hairong,Cai, Yan,Miao, Xinyu,Miao, Zhiwei
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- Facile microwave-assisted one-pot solid phase synthesis of spiro[3H-indole-3,4′-pyrazolo[3,4-b] pyridines]
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A rapid, enviro-economic protocol for the novel one-pot synthesis of a series spiro [3H-indole-3,4′-pyrazolo[3,4-b]pyridines (7a-f) under microwave irradiation is described. The intermediates spiro pyrazolopyran (5) and dicyanomethylene indole-2-one (3) w
- Dandia, Anshu,Arya, Kapil,Sati, Meha,Sharma, Rekha
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- Synthesis of novel 2-oxospiro[indoline-3,4′-[1,3]dithiine]-5′-carbonitrile derivatives by new spiro[indoline-3,4′-[1,3]dithiine]?Cu(NO3)2 supported on Fe3O4?gly?CE MNPs as efficient catalyst and evaluation of biological activity
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New spiro[indoline-3,4′-[1,3]dithiine]?Cu(NO3)2 supported on Fe3O4?gly?CE magnetic nanoparticle were synthesized and used as efficient and recyclable catalyst in the synthesis of 2-oxospiro[indoline-3,4′-[1,3]dithiine]-5′-carbonitrile derivatives. The structure of magnetic nanoparticles were confirmed using energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA), infrared spectroscopy (FT-IR) and inductively coupled plasma optical emission spectroscopy (ICP-OES). Subsequently, antibacterial and antifungal activities in terms of inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration and antioxidant activity against the DPPH free radical of the derivatives were investigated. The results revealed acceptable biological effects of the synthetic derivatives and a significant relationship between their structure and biological activity were observed.
- Akhgar, Mohammadreza,Ghazanfari, Dadkhoda,Moghaddam-Manesh, Mohammadreza,Sheikhhosseini, Enayatollah
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- Regio- and stereoselective synthesis of novel dispiropyrrolidine: Bisoxindole derivatives via multicomponent reactions
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A convenient and efficient method for the synthesis of novel dispiropyrrolidine bisoxindole derivatives by 1,3-dipolar cycloaddition reaction of azomethine ylides has been developed. The synthesis was achieved by using a one-pot multicomponent procedure. The features of this procedure were characterized by the following: mild reaction conditions, high yields, high regio- and stereoselectivity, one-pot procedure, and operational simplicity.
- Liu, Hai,Dou, Guolan,Shi, Daqing
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- Four-Component Reaction Access to Nitrile-Substituted All-Carbon Quaternary Centers
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A four-component reaction strategy for access to acyclic nitrile-substituted all-carbon quaternary centers is disclosed. In the presence of a DABCO-based ionic liquid catalyst, the reactions proceed smoothly with a wide range of substrates efficiently to deliver nitrile-substituted all-carbon quaternary centers under mild reaction conditions. This protocol is further demonstrated as an efficient method for the construction of contiguous all-carbon quaternary centers. All the reactions are easily operated in a green manner, producing water as the only byproduct. Some of the products show excellent activity against specific fungi.
- Bian, Qiang,Guo, Lin-Jie,Hu, Xin,Wang, Ge,Wang, Zheng-Lin,Xu, Da-Zhen,Xu, Yi-Ze
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- Site-specific role of bifunctional graphitic carbon nitride catalyst for the sustainable synthesis of 3,3-spirocyclic oxindoles in aqueous media
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Functionalized graphitic carbon nitride (Sg-C3N4) has been manufactured and used as a reusable catalyst for the one-pot production of various spiro-pyrano chromenes and spiro indole-3,1′-naphthalene tetracyclic systems in aqueous med
- Dandia, Anshu,Mahawar, Dinesh Kumar,Saini, Pratibha,Saini, Surendra,Gupta, Shyam L.,Rathore, Kuldeep S.,Parewa, Vijay
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p. 28452 - 28465
(2021/09/22)
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- A Simplistic Approach for Preparation of Alkylidenemalononitrile Derivatives: Characterization, In silico Studies, Quantum Chemical Evaluation, Molecular Docking, and In vitro Biological Activity Evaluation
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A new and efficient green grinding-based catalyst free Knoevenagel condensation of aldehydes/ketones and malononitrile for the rapid preparation of twelve malononitrile derivatives (C1-C12) is proposed. Characterization of the derivatives was done by sup
- Ahmad, Rumana,Azad, Iqbal,Kamal, Azhar,Khan, Abdul Rahman,Khan, Tahmeena,Nasibullah, Malik
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- Chrysin spliced pyran spiro oxoindole compound, preparation method and application thereof
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The invention discloses a chrysin spliced pyran spiro oxoindole compound, which is a first chrysin spliced spiro oxoindole derivative and a first flavone spliced spiro oxoindole derivative, and can provide a compound source for bioactivity screening, and has important application value in drug screening and pharmaceutical industry. The method is simple and feasible to operate, the raw materials are cheap in synthesisand easily available, the chrysin spliced pyran spiro oxoindole compound can be subjected to various organic solvents, has relatively good air stability, wide applicability and very good compatibility with various substituent groups. The skeleton compound has a tumor growth inhibition activity effect on human leukemia cells (K562), human lung adenocarcinoma cells (A549), humanlung adenocarcinoma cells (H1299) and human prostate cancer cells (PC-3).
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Paragraph 0039
(2021/03/03)
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- Diastereoselective [3 + 1] Cyclization Reaction of Oxindolyl Azaoxyallyl Cations with Sulfur Ylides: Assembly of 3,3′-Spiro[β-lactam]-oxindoles
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Oxindoles and β-lactams are attractive structural motifs because of their unique biological importance. However, the fusion of the two moieties featuring 3,3′-spirocyclic scaffolds is a challenging task in organic synthesis. Herein we designed a novel type of oxindole-based azaoxyallyl cation synthons, which could readily participate in the [3 + 1] cyclization with sulfur ylides. With this protocol, a collection of 3,3-spiro[β-lactam]-oxindoles were facilely produced in up to 94% yield with perfect diastereoselectivity.
- Leng, Hai-Jun,Li, Qing-Zhu,Xiang, Peng,Qi, Ting,Dai, Qing-Song,Jia, Zhi-Qiang,Gou, Chuan,Zhang, Xiang,Li, Jun-Long
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supporting information
p. 1451 - 1456
(2021/03/08)
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- Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon-carbon double bond formation
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The iron-catalyzed cross-dehydrogenative coupling (CDC) of C(sp3)-H/C(sp3)-H bonds to afford olefins by 4H elimination is described. This method employs air (molecular oxygen) as an ideal oxidant, and is performed under mild, ligand-free and base-free conditions. H2O is the only byproduct. Good tolerance of functional groups and high yields have also been achieved. Preliminary mechanistic investigations suggest that the present transformation involves a radical process.
- Tan, Zhi-Yu,Wu, Ke-Xin,Huang, Lu-Shan,Wu, Run-Shi,Du, Zheng-Yu,Xu, Da-Zhen
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p. 332 - 335
(2020/02/13)
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- Eosin Y-catalyzed one-pot synthesis of spiro[4H-pyran-oxindole] under visible light irradiation
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An efficient and simple synthetic approach has been developed for the preparation of biologically interesting spiro[oxindole-3,4’-(4′H-pyran)] derivatives via visible light-mediated one-pot, three-component reaction of isatins, 1,3-dicarbonyl compounds an
- Chen, Meng-Nan,Di, Jia-Qi,Li, Jiao-Mian,Mo, Li-Ping,Zhang, Zhan-Hui
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- 3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium
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The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used
- Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Satyanarayana, Neeli,Kashinath, Dhurke
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p. 14045 - 14050
(2019/09/18)
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- Iron-catalyzed one-pot oxidation/Knoevenagel condensation reaction using air as an oxidant
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A green and highly efficient iron-catalyzed one-pot oxidation/Knoevenagel tandem reaction for the synthesis of α, β-unsaturated nitriles from secondary alcohols and malononitrile has been achieved. The reaction performed under mild conditions with air as
- Huang, Lu-Shan,Lai, Yi-Huan,Yang, Cheng,Xu, Da-Zhen
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- Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles
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A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit
- Liu, Yingtian,Dang, Xinxin,He, Yu,Bai, Hudong,Chen, Xuehong,Li, Jun-Long,Fan, Junting,Jiang, Hezhong,Li, Jiahong
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p. 662 - 671
(2019/02/20)
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- Bifunctional Squaramide-Catalyzed Asymmetric [3 + 2] Cyclization of 2-(1-Methyl-2-oxoindolin-3-yl)malononitriles with Unsaturated Pyrazolones to Construct Spirooxindole-Fused Spiropyrazolones
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The present paper reports a highly stereoselective synthesis of spirooxindole-fused spiropyrazolones through the asymmetric [3 + 2] cyclization reaction of 2-(1-methyl-2-oxoindolin-3-yl)malononitriles with unsaturated pyrazolones under mild conditions. Wi
- Lin, Ye,Zhao, Bo-Liang,Du, Da-Ming
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p. 10209 - 10220
(2019/09/04)
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- Synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives: Via a multi-component cascade reaction of α-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate
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We report a green synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives which are of potential value in medicinal chemistry. We are able to access spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives via a Cu(OTf)2-catalyzed or Cu(OTf)2/Rh2(OAc)4-cocatalyzed multi-component cascade reaction of α-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate. The reaction can be accomplished in good to excellent yields (60-99%), and the structure of products 6a and 6k was supported by X-ray crystallography. The catalyst Cu(OTf)2 can be recycled 4 times without a sharp loss of the yield of 6a. 6q can be easily synthesized in gram scale. In brief, the reaction is characterized by step economy, a harmless solvent, and a recyclable catalyst.
- Shi, Taoda,Teng, Shenghan,Wei, Yajie,Guo, Xin,Hu, Wenhao
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supporting information
p. 4936 - 4940
(2019/09/30)
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- Design, synthesis and evaluation of structurally diverse chrysin-chromene-spirooxindole hybrids as anticancer agents
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A series of structurally diverse chrysin-chromene-spirooxindole hybrids were designed, synthesized via a Knoevenagel/Michael/cyclization of chrysin and isatylidene malononitrile derivatives through utilizing a hybrid pharmacophore approach. The newly synthesized compounds were evaluated for their in vitro anticancer activity, and most of the compounds showed stronger anti-proliferative activity than parent compound chrysin. In particular, compound 3e had the highest cytotoxicity towards A549 cells (IC50 = 3.15 ± 0.51 μM), and had better selectivity in A549 cells and normal MRC-5 cells. Furthermore, compound 3e could significantly inhibit the proliferation and migration of A549 cells in a dose-dependent manner, as well as induce the apoptosis possibly through mitochondria-mediated caspase-3/8/9 activation and multi-target co-regulation of the p53 signaling pathway. Thus, our results provide in vitro evidence that compound 3e may be a potential candidate for the development of new anti-tumour drugs.
- Zhang, Wen-Hui,Chen, Shuang,Liu, Xiong-Li,Feng, Ting-Ting,Yang, Wu-De,Zhou, Ying
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- Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles
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The exploration of catalytic potential of natural amino acid salt in activation of 1,3-dicarbonyls was carried out, in which maleimides and 2-(2-oxoindolin-3-ylidene)malononitriles were found to be good electrophiles and afforded the desired products with excellent yield and moderate optical purity. Control experiments showed that the secondary amino group of barium (S)-prolinate is critical to the catalytic activity as well as enantiocontrol, thus revealed an enamine activation mechanism is possible in the present methodology.
- Jiang, Jun,Li, Juan,Li, Xinhua,Liu, Hongxin,Wu, Haiyan,Xiao, Hong-Ping
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supporting information
p. 1241 - 1245
(2019/06/08)
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- Dihydro-2: H -thiopyran-3(4 H)-one-1,1-dioxide-a versatile building block for the synthesis of new thiopyran-based heterocyclic systems
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Three series of new cyclic sulfones have been prepared by a one-pot multi-component reaction (MCR) starting from the readily available dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide. The in silico screening of the synthesized compounds revealed their high anti-inflammatory, antiarthritic, antiasthmatic and antiallergic potential coupled with the strong probability levels of cystinyl aminopeptidase inhibition. The key structures were confirmed by 2D NMR techniques.
- Palchykov, Vitalii A.,Chabanenko, Roman M.,Konshin, Valeriy V.,Dotsenko, Victor V.,Krivokolysko, Sergey G.,Chigorina, Elena A.,Horak, Yuriy I.,Lytvyn, Roman Z.,Vakhula, Andriy A.,Obushak, Mykola D.,Mazepa, Alexander V.
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p. 1403 - 1412
(2018/02/06)
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- An expedient synthesis of spirooxindoles incorporating 2-amino pyran-3-carbonitrile unit employing dialkyl acetone-1,3-dicarboxylates
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Spirooxindoles are a class of molecules possessing significant biological effects such as antiviral, antifungal, antibacterial and anticancer properties. Herein we report a series of spirooxindole molecules having 2-amino pyran-3-carbonitrile and with two ester groups. These molecules were prepared by the reaction of dialkyl acetone-1,3-dicarboxylate and isatilidenes in the presence of triethyl amine.
- Satheesh, Monisha,Balachandran, Aswathy L.,Devi, Parvathi R.,Deepthi, Ani
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supporting information
p. 582 - 587
(2018/02/16)
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- TiCl4/DMAP mediated: Z -selective knovenagel condensation of isatins with nitroacetates and related compounds
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A highly efficient Z-selective Knovenagel condensation reaction of isatins with nitroacetates mediated by TiCl4 and DMAP was described. The desired 2-nitro-3-ylideneoxindole acetates were obtained in good to excellent stereoselectivities and yields. Other activated methylene derivatives as well as 4-methylbenzenesulfonamide could provide good results too. This method makes it possible to obtain various unreported 3-ylideneoxindole derivatives under mild reaction conditions.
- Zhu, Luyi,Yan, Peipei,Zhang, Lvye,Chen, Zhangtao,Zeng, Xiaofei,Zhong, Guofu
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p. 51352 - 51358
(2017/11/15)
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- Ionic Liquid Mediated Green Synthesis of Spirooxindoles from N-methyl Quinolones and Their Anti Bacterial Activity
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Three-component reaction involving condensation of 1-methyl quinoline-2,4(1H,3H)-dione 1, isatins 2(a–e), and malononitrile/cyanoacetic ester 3(a–b) in the task-specific ionic liquid [DBU][Ac] (1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate) leading to the spirooxindole derivatives 4(a–j) is described. This approach is affords the products in high yields without use of column chromatography and resulting compounds were evaluated for antibacterial activity against both gram positive and gram negative bacteria (Staphylococcus aureus, Escherichia coli, Bacillus cereus, Bacillus subtilis, Salmonella typhimurium, and Klebsiella pneumonia). Among the all compounds, four compounds, that is, 4b, 4e, 4f, 4g, 4j exhibited moderate activity against all the strains as compared with the standard used.
- Bhupathi, Raja S.,Madhu, Bandi,Reddy, Ch. Venkata Ramana,Devi, B. Rama,Dubey
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p. 2326 - 2332
(2017/07/25)
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- Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast
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3-Substituted oxindoles are very interesting molecules both for their potential biological activity and for their role as starting materials toward more complex oxindole-based structures. These molecules can be prepared by the reduction of a 3-ylidene oxi
- Rossetti, Arianna,Sacchetti, Alessandro,Bonfanti, Marta,Roda, Gabriella,Rainoldi, Giulia,Silvani, Alessandra
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p. 4584 - 4590
(2017/07/11)
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- A Tunable and Enantioselective Hetero-Diels–Alder Reaction Provides Access to Distinct Piperidinoyl Spirooxindoles
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The active complexes of chiral N,N′-dioxide ligands with dysprosium and magnesium salts catalyze the hetero-Diels–Alder reaction between 2-aza-3-silyloxy-butadienes and alkylidene oxindoles to selectively form 3,3′- and 3,4′-piperidinoyl spirooxindoles, respectively, in very high yields and with excellent enantioselectivities. The exo-selective asymmetric cycloaddition successfully regaled the construction of sp3-rich and highly substituted natural-product-based spirooxindoles supporting many chiral centers, including contiguous all-carbon quaternary centers.
- Jayakumar, Samydurai,Louven, Kathrin,Strohmann, Carsten,Kumar, Kamal
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supporting information
p. 15945 - 15949
(2017/11/27)
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- A One-Pot, Multicomponent Synthesis of 5′-Amino-2,2′-dioxospiro[indoline-3,3′-pyrrole]-4′-carbonitriles
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A novel, one-pot, multicomponent synthesis of 5′-amino-2,2′-dioxospiro[indoline-3,3′-pyrrole]-4′-carbonitriles is described. The Knoevenagel condensation reaction between isatin derivatives and malononitrile gave the corresponding cyclic arylmethylidenema
- Adib, Mehdi,Yasaei, Zahra,Mirzaei, Peiman
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p. 383 - 386
(2016/02/14)
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- [bmim]OH: An efficient catalyst for the synthesis of mono and bis spirooxindole derivatives in ethanol at room temperature
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A rapid and efficient, one pot synthesis of spirooxindole derivatives has been attempted by three-component reaction of isatin, malononitrile and carbonyl compound possessing a reactive α-methylene group by using task specific ionic liquid, 1-butyl-3-meth
- Padvi, Swapnil A.,Tayade, Yogesh A.,Wagh, Yogesh B.,Dalal, Dipak S.
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p. 714 - 720
(2016/05/19)
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- DABCO catalyzed pseudo multi-component synthesis of functionalized spirooxindoles
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Abstract: A direct multi-component assembling of isatin, cyclohexanone, and 2?mol of malononitrile in the presence of catalytic amount of DABCO in aq. ethanol leads to functionalized spirooxindoles at ambient temperature. The novelties of the method are m
- Hegade, Pravin G.,Chinchkar, Sarika D.,Pore, Dattaprasad M.
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p. 1243 - 1249
(2016/07/30)
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- Molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction: Efficient and mild conditions for the synthesis of 3,3-disubstituted oxindoles with an all carbon quaternary center
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A one-pot, molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction has been developed. We discovered that the molecular sieves not only promoted the Knoevenagel condensation of isatins and malononitrile to generate isatylidene malononitriles, but also promoted the later decarboxylative Michael addition reactions of β-ketoacids and malonic acid half thioesters (MAHTs) with isatylidene malononitriles. This protocol provides a mild and efficient method for the preparation of 3,3-disubstituted oxindoles with an all carbon quaternary center in high yields.
- Guo, Yi-Lin,Li, Yu-Hsun,Chang, Hsuan-Hao,Kuo, Ting-Shen,Han, Jeng-Liang
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p. 74683 - 74690
(2016/08/24)
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- Bioreduction of the C=C double bond with Pseudomonas monteilii ZMU-T17: One approach to 3-monosubstituted oxindoles
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An efficient whole cell-mediated bioreduction of 3-methylene-2-oxindoles has been developed, affording a range of 3-monosubstituted oxindoles in moderate to good yields (41-82%) with Pseudomonas monteilii ZMU-T17 as biocatalyst. Additionally, a possible reaction pathway for this bioreduction of C=C double bond was proposed.
- Zhao, Jia,Guan, Shuicheng,Zhou, Xiaojian,Han, Wenyong,Cui, Baodong,Chen, Yongzheng
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p. 3098 - 3104
(2016/05/19)
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- Ordered short channel mesoporous silica modified with 1,3,5-triazine-piperazine as a versatile recyclable basic catalyst for cross-aldol, Knoevenagel and conjugate addition reactions with isatins
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A triazine-piperazine immobilized on ordered short channel mesoporous silica was synthesized, characterized and used as a heterogeneous basic catalyst in the synthesis of indole skeletal structures from isatin derivatives under ambient reaction conditions in good to excellent isolated yields. The catalyst showed no loss in its efficacy over 10 recycle experiments. This journal is
- Gupta, Naveen,Roy, Tamal,Ghosh, Debashis,Abdi, Sayed H. R.,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Bajaj, Hari C.
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p. 17843 - 17850
(2015/03/04)
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- Biocatalytic one-pot three-component synthesis of 3,3′-disubstituted oxindoles and spirooxindole pyrans using α-amylase from hog pancreas
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α-Amylase from hog pancreas displayed catalytic promiscuity in three-component reaction for the synthesis of 3,3′-disubstituted oxindoles and spirooxindole pyrans. The reactions between isatins, malononitrile and active methyl or active methylene compounds (acetone, nitromethane, indole, acetylacetone, 4-hydroxylcoumarin and dimedone) offered corresponding products via Knoevenagel/Michael reactions or Knoevenagel/Michael/cyclization reactions in one pot with high to excellent yields of up to 98% under mild reaction conditions. The α-amylase showed a broad spectrum of adaptability to various substrates. A possible mechanism of the α-amylase catalyzed three-component reaction was proposed. This journal is
- He, Tao,Zeng, Qing-Qing,Yang, Da-Cheng,He, Yan-Hong,Guan, Zhi
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p. 37843 - 37852
(2015/05/13)
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- Palladium-catalyzed asymmetric allylic amination of racemic butadiene monoxide with isatin derivatives
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Isatins and their derivatives are important functional moities and building blocks in pharmaceutical and synthetic chemistry. Numerous enantioselective transformations at the C-3 carbonyl group have been well developed. However, the asymmetric substitution reaction with isatins and their derivatives as nucleophiles based on the free N-H groups has been less studied due to the relatively weaker nucleophilicity resulting from the two electron-withdrawing carbonyl groups. In this paper, a palladium-catalyzed asymmetric allylic amination of racemic butadiene monoxide with isatin derivatives using a chiral phosphoramidite olefin hybrid ligand has been successfully developed under mild conditions. A variety of chiral amino alcohols were afforded in 55-87% yields with 10/1->20/1 regioselectivity ratios and 80-97% ees.
- Li, Gen,Feng, Xiangqing,Du, Haifeng
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supporting information
p. 5826 - 5830
(2015/05/27)
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- Knovenagel condensation of isatin with nitriles and 1, 3-diketones
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Knoevenagel condensation of isatin 1 with some nitriles 2 and with cyclohexane-1,3-diones 4 using piperidinium acetate as catalyst in water at 100°C results in the formation of α,β - unsaturated products, i.e. 2-(2-oxo-1,2-dihydro-indol-3- ylidene)-malono
- Riyaz,Indrasena,Naidu,Dubey
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p. 120 - 123
(2014/02/14)
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- Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs
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Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with spiro heterocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenone framework were designed and synthesized. Insecticidal evaluation showed that some of spirobenzofuranone containing neonicotinoids exhibited moderate activity against cowpea aphid, armyworm or brown planthopper.
- Chen, Nan-Yang,Ren, Li-Ping,Zou, Min-Ming,Xu, Zhi-Ping,Shao, Xu-Sheng,Xu, Xiao-Yong,Li, Zhong
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p. 197 - 200
(2014/02/14)
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- P-C bond formation via direct and three-component conjugate addition catalyzed by ZnO nano-rods for the synthesis of 2-oxindolin-3-yl-phosphonates under solvent-free conditions
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A simple and novel method is reported for the synthesis of 2-oxindolin-3-yl-phosphonates using ZnO nano-rods as a catalyst under solvent-free conditions at room temperature. ZnO nano-rods are synthesized successfully by employing Zn(OAc)2·2Hsu
- Hosseini-Sarvari, Mona,Tavakolian, Mina
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experimental part
p. 1014 - 1021
(2012/07/14)
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- Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c]pyrazoles
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An ecofriendly green approach for synthesis of substituted pyrano[2,3-c]pyrazoles has been developed via a multicomponent one pot approach in aqueous ethanol medium under totally non-catalytic conditions. The synthesized compounds were evaluated for their
- Mandha, Santhosh Reddy,Siliveri, Sravanthi,Alla, Manjula,Bommena, Vittal Rao,Bommineni, Madhava Reddy,Balasubramanian, Sridhar
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scheme or table
p. 5272 - 5278
(2012/09/07)
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- Reactions of 2′-oxo-1′,2′-dihydrospiro[cyclopropane-1, 3′-indole]-2,2,3,3-tetracarbonitriles with nucleophiles
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2′-Oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole] -2,2,3,3-tetracarbonitriles reacted with oxygencentered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the presence of base catalyst, and the products, 2-amino-4,4-dialkoxy-2′-oxo-1′, 2′-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1, 5-dicarbonitriles, were converted into the corresponding 2-imino-2′,4- dioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1,5-dicarbonitriles and 2,2′,4-trioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1, 5-dicarbonitriles by the action of acetic and sulfuric acids, respectively. The reactions with ketone oximes occurred in the absence of a catalyst, yielding 2-amino-4,4-bis(alkylideneaminooxy)-2′-oxo-1′,2′- dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1, 5-dicarbonitriles. The reactions with thiols, aliphatic amines, and anilines were accompanied by opening of the three-membered ring. In the reactions with triphenylphosphine and thiols 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene) malononitrile was obtained, while morpholine and N,N-dimethylaniline gave rise, respectively, to 3,3-diaryl-and 3,3-dimorpholino-1H-indol-2(3H)-ones and tri- and dicyanoethylene derivatives.
- Kayukov, Ya. S.,Kayukova,Kalyagina,Bardasov,Ershov,Nasakin,Tafeenko
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experimental part
p. 392 - 401
(2011/06/21)
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- 'On water' Knoevenagel condensation of isatins with malononitrile
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Grinding of isatins with malononitrile in the presence of 1-5 equiv. of water for 15 min at room temperature affords the corresponding (2-oxo-1,2-dihydro-3H-indol-3-ylidene)malononitriles, the Knoevenagel condensation products, in 89-99% yields.
- Demchuk, Dmitry V.,Elinson, Michail N.,Nikishin, Gennady I.
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experimental part
p. 224 - 225
(2011/10/18)
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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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scheme or table
p. 5693 - 5699
(2011/08/22)
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- A facile strategy for the one pot multicomponent synthesis of spiro dihydropyridines from amines and activated alkynes
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An efficient preparation of a series of spiro dihydropyridines via one pot four-component reactions of mono/di/tri-ketones, malononitrile, primary amines, and acetylenic esters is reported. The reaction is atom-efficient, high yielding, and follows a simp
- Kiruthika, Selvarangam E.,Lakshmi, Neelakandan Vidhya,Banu, Babu Rasidha,Perumal, Paramasivan T.
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experimental part
p. 6508 - 6511
(2011/12/21)
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- DBU-Catalyzed, facile and efficient method for synthesis of spirocyclic 2-oxindole derivatives with incorporated 6-amino-4H-pyridazines and fused derivatives via [3+3] atom combination
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3-Cyanomethylidene oxindole derivatives were prepared in excellent yields utilizing DBU-promoted Knoevenagel condensation of isatin derivatives with active methylene reagents. The isolated products were then reacted with azaenamines via a DBU-promoted Mic
- Abdelhamid, Ismail A.,Mohamed, Mona H.,Abdelmoniem, Amr M.,Ghozlan, Said A.S.
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experimental part
p. 10069 - 10073
(2010/02/27)
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- Synthesis of novel spiro cyclic 2-oxindole derivatives of 6-amino-4H-pyridazine via [3+3] atom combination utilizing chitosan as a catalyst
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Azaenamines were reacted with 3-cyanomethylidene-2-oxindoles using chitosan catalyst to yield spirocyclic 2-oxindole derivatives of 6-amino-4H-pyridazine and fused pyridazinoquinazolines. Georg Thieme Verlag Stuttgart.
- Abdelhamid, Ismail Abdelshafy
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body text
p. 625 - 627
(2009/07/10)
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- Microwave-assisted synthesis of new spiro[indoline-3,4'-quinoline] derivatives via a one-pot multicomponent reaction
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A simple and efficient synthesis of spiro[indoline-3,4'-quinoline] derivatives by a one-pot reaction of isatin, malononitrile, and enaminone under microwave irradiation was investigated. This protocol has the advantages of short reaction time, high yields
- Zhu, Song-Lei,Zhao, Kai,Su, Xiao-Ming,Ji, Shun-Jun
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experimental part
p. 1355 - 1366
(2009/10/09)
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- Facile one-pot synthesis of new annulated hexacyclic ring system indeno-pyranofuro-indoles and spiro indenopyran-indoles under microwave irradiation
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An efficient and clean procedure for the synthesis of a new hexacyclic system indeno-pyrano-furo-indoles 8 and spiroindoles incorporating pentacyclic ring system spiro[indenopyran-indoles] 6 using inorganic solid support under microwave irradiation is described.
- Dandia, Anshu,Singh, Ruby,Singh, Dharmendra
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body text
p. 1001 - 1005
(2009/12/26)
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- Mn(III)-based radical addition reactions of 2-nitroindole with activated CH compounds
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2-Nitroindole undergoes addition reactions with the radicals generated from active CH compounds upon treatment with Mn(OAc)3·2H2O to afford the corresponding 3-substituted-2-nitroindoles in 27-66% yields. Products of the methylene addition reactions undergo a subsequent in situ Nef reaction to afford 2-oxoindolin-3-ylidenes.
- Androsov, Dmitry A.,Kishbaugh, Tara L.S.,Gribble, Gordon W.
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body text
p. 6621 - 6623
(2009/04/06)
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- Synthesis and molecular structure of spirocyclic 2-oxindole derivatives of 2-amino-4H-pyran condensed with the pyrazolic?nucleus
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4,3′-Spiro[(6-amino-5-R-3-methyl-2H,4H-pyrano[2,3-c]pyrazolo)-2′-oxindoles] were synthesized based on the three-component condensation of isatins with 3-methyl-pyrazolone-5 and respective methylene active nitriles in the presence of basic catalysts. The m
- Redkin, Ruslan Gr.,Shemchuk, Leonid A.,Chernykh, Valentine P.,Shishkin, Oleg V.,Shishkina, Svetlana V.
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p. 11444 - 11450
(2008/03/13)
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- Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents
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Several new spiro indoline-based heterocycles were synthesized by prior preparation of the 4-(2′-oxo-indol-3′-ylidene) -oxazol-5-one derivatives and subsequent reaction of the produced indol-3-ylidene based heterocycles with activated nitrile reagents. The obtained products were allowed to react with hydrazine hydrate in alcoholic basic to give the target compounds. Structure of these products was confirmed on the bases of elemental as well as spectral data. Representative compounds of the hitherto synthesized products were tested and evaluated as antimicrobial agents.
- Abdel-Rahman,Keshk,Hanna,El-Bady
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p. 2483 - 2488
(2007/10/03)
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- Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester
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The Hantzsch 1,4-dihydropyridine ester (1) has been observed to be a useful selective reducing agent for the reduction of electron-withdrawing conjugated double bonds. The rate of this reaction was observed to be dependent upon the nature of the conjugate
- Garden, Simon J.,Werneck Guimaraes, Cristiano Ruch,Correa, Marilza B.,Fernandes de Oliveira, Cesar Augusto,Da Cunha Pinto, Angelo,Bicca de Alencastro, Ricardo
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p. 8815 - 8822
(2007/10/03)
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- On the reaction of isatin with cyanomethylene(triphenyl)phosphorane. A nucleophilic attack of alkyl phosphites on the carbon-carbon double bond of (E)-oxindolylideneacetonitrile
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The reaction of cyanomethylene(triphenyl)phosphorane (2) with isatin (1) in dry benzene at room temperature for 1 h led to the formation of (1,2- dihydro-2-oxo-3H-indol-3-yl)acetonitrile as a mixture of E- and Z-stereo isomers 3 and 4. Trialkyl phosphites 7 reacted with (E)-nitrile 3 in dry benzene at 70°C for about 10 h to give the phosphonates 8 as two isomers together with the unexpected spiro products of isomers 9. When the (E)- nitrile 3 was allowed to react with dialkyl phosphites (11) without solvents at 100°C for about 30 h, a mixture of the phosphonate derivatives 8 and one isomer of the dimeric structure 9 were obtained. The reaction mechanisms are considered and the structural assignments of the new compounds are based on chemical and spectroscopic evidence. (C) 2000 Elsevier Science Ltd.
- Osman, Fayez H.,El-Samahy, Fatma A.
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p. 1863 - 1871
(2007/10/03)
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