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Journal articles on the topic 'Oxindole'

Author: Grafiati
Published: 4 June 2021
Last updated: 25 July 2025

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1

Ziarani, Ghodsi Mohammadi, Fatemeh Javadi, and Fatemeh Mohajer. "The Molecular Diversity Scope of Oxindole Derivatives in Organic Synthesis." Current Organic Chemistry 25, no. 7 (2021): 779–818. http://dx.doi.org/10.2174/1385272825666210111112814.

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The role of oxindole derivatives is discussed as starting materials in diverse organic reactions, including two and more components, between the years 2014 until 2020. Oxindoles are famous because of their biological properties. For instance, chromanone-fused polycyclic pyrrolidinyl-dispirooxindoles, functionalized polycyclic spiro-fused carbocyclicoxindole, and 3,3-disubstituted oxindoles have anti-cancer, anti-tumor, and anti-microbial properties, respectively. Therefore, various methods for synthesizing the oxindole structures have received much attention in organic chemistry.
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2

Lingam, Kandapalam, Kodirajan Selvakumar, Periyasamy Amutha, and Paneerselvam Yuvaraj. "Controlled and Efficient Stereoselective Synthesis of Oxindole-Appended 1-Aza-1,3-butadiene Derivatives via a One-Pot Buchwald–Hartwig Amination/Elimination Strategy." Synthesis 50, no. 03 (2017): 599–606. http://dx.doi.org/10.1055/s-0036-1591493.

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The enamine-free, stereoselective synthesis of oxindole-appended­ 1-aza-1,3-butadienes with an electron-withdrawing-group at the 3-position has been achieved in good yields from (Z)-β-bromo-substituted Morita–Baylis–Hillman (MBH) adducts of oxindoles via a one-pot Buchwald–Hartwig amination/elimination strategy. The versatility of the (Z)-β-bromo MBH adducts of oxindoles was further demonstrated by the formation of π-conjugated oxindole derivatives in typical palladium­-catalysed coupling reactions.
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3

Koo, Jahyun, Minsu Kim, Kye Jung Shin, and Jae Hong Seo. "Non-Palladium-Catalyzed Approach to the Synthesis of (E)-3-(1,3-Diarylallylidene)Oxindoles." Molecules 27, no. 16 (2022): 5304. http://dx.doi.org/10.3390/molecules27165304.

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Two novel synthetic approaches for synthesizing (E)-3-(1,3-diarylallylidene)oxindoles from oxindole were developed. All previously reported methods for synthesizing 3-(1,3-diarylallylidene)oxindoles utilized palladium-catalyzed reactions as a key step to form this unique skeleton. Despite high efficiency, palladium-catalyzed reactions have limitations in terms of substrate scope. Especially, an iodoaryl moiety cannot be introduced by the previous methods due to its high reactivity toward the palladium catalyst. Our Knoevenagel/allylic oxidation/Wittig and Knoevenagel/aldol/dehydration strategi
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4

Jackson, Mark, Calvin Quince O'Broin, Helge Müller-Bunz та Patrick J. Guiry. "Enantioselective synthesis of sterically hindered α-allyl–α-aryl oxindoles via palladium-catalysed decarboxylative asymmetric allylic alkylation". Organic & Biomolecular Chemistry 15, № 38 (2017): 8166–78. http://dx.doi.org/10.1039/c7ob02161e.

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5

Cong, Tiantian, Huamin Wang, Xiuzheng Li, Hai-Hong Wu, and Junliang Zhang. "Chiral bifunctional bisphosphine enabled enantioselective tandem Michael addition of tryptamine-derived oxindoles to ynones." Chemical Communications 55, no. 62 (2019): 9176–79. http://dx.doi.org/10.1039/c9cc04357h.

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A chiral phosphine-catalyzed tandem Michael addition of tryptamine-derived oxindoles to ynones was developed to synthesize spiro[pyrrolidine-3,3′-oxindole] in good yields, good to excellent enantio- and diastereoselectivities.
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6

Du, Da-Ming, and Yong-Xing Song. "Squaramide-Catalyzed Asymmetric Michael/Cyclization Cascade Reaction of Unsaturated Thiazolidinones and 3-Isothiocyanato Oxindoles: Synthesis of New Bispirocyclic Heterocycles." Synthesis 50, no. 07 (2018): 1535–45. http://dx.doi.org/10.1055/s-0036-1591527.

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A highly efficient method for the construction of oxindole-pyrrolidone-thiazolidinone bispirocyclic heterocycles bearing three contiguous chiral centers including two quaternary one via a Michael/cyclization cascade reaction has been developed. Using bifunctional cinchona-derived squaramide as catalyst, the reactions of 3-isothio­cyanato oxindoles with unsaturated thiazolidinone derivatives proceeded smoothly under mild reaction conditions to afford a series of complex chiral oxindole-pyrrolidone-thiazolidinone bispirocyclic heterocycles in high yields (up to 99%) with excellent diastereo- and
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7

Wang, Ying, Tianzi Wei, Man Zhao, et al. "Alkenyl oxindole is a novel PROTAC moiety that recruits the CRL4DCAF11 E3 ubiquitin ligase complex for targeted protein degradation." PLOS Biology 22, no. 5 (2024): e3002550. http://dx.doi.org/10.1371/journal.pbio.3002550.

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Alkenyl oxindoles have been characterized as autophagosome-tethering compounds (ATTECs), which can target mutant huntingtin protein (mHTT) for lysosomal degradation. In order to expand the application of alkenyl oxindoles for targeted protein degradation, we designed and synthesized a series of heterobifunctional compounds by conjugating different alkenyl oxindoles with bromodomain-containing protein 4 (BRD4) inhibitor JQ1. Through structure-activity relationship study, we successfully developed JQ1-alkenyl oxindole conjugates that potently degrade BRD4. Unexpectedly, we found that these molec
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8

Cui, Hao, Ke Li, Yue Wang, et al. "Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones." Organic & Biomolecular Chemistry 18, no. 19 (2020): 3740–46. http://dx.doi.org/10.1039/d0ob00546k.

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A copper/Ganphos-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described, producing the spiro[pyrrolidin-3,3′-oxindole]s in good yields with high ee.
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9

Li, Chao, Wei-Huan Li, and Lin Dong. "Efficient synthesis of N-butadiene substituted oxindole derivatives." Organic Chemistry Frontiers 5, no. 23 (2018): 3460–63. http://dx.doi.org/10.1039/c8qo00930a.

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A novel rhodium(iii)-catalyzed amide carbonyl group directed alkenylation reaction between oxindoles and alkenes has been reported, which provides an efficient method for the synthesis of valuable and versatile functionalized N-(2E,4Z)-butadiene substituted oxindole derivatives.
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10

Wu, Mingshu, Dulin Kong, Tiao Huang, Li Liu, and Qinghe Wang. "1,3-Dipolar Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and O-Vinylphosphonylated Salicylaldehydes for Diastereoselective Synthesis of Oxindole Spiro-P,N-polycyclic Heterocycles." Synthesis 52, no. 09 (2020): 1387–97. http://dx.doi.org/10.1055/s-0039-1691597.

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An efficient stereoselective assembly strategy for the construction of pyrrolidin-2,3′-oxindole cis-fused phosphadihydrocoumarins was established. The process involves the condensation of O-vinylphosphonylated salicylaldehydes and 3-amino oxindoles followed by intermolecular cycloaddition with high diastereoselectivity and atom economy.
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11

M, Heravi; Majid, A. Feiz, B. Notash, and A. Bazgir. "Synthesis of oxindolyl-pyrimidines and oxindolyl-furopyrimidines from isatin-derived propargylic alcohols." Journal of the Iranian Chemical Society 17, no. 7 (2020): 1743–51. https://doi.org/10.1007/s13738-020-01893-3.

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A Brønsted acid-catalyzed reaction of 6-amino uracil and isatin-derived propargylic alcohols for the synthesis of a series of oxindole-fused pyrimidine in good-to-high yields was achieved (up to 94%). Furthermore, the reaction of isatin-derived propargylic alcohols and 1,3-dimethylbarbituric acid or ethyl 3-aminocrotonate gave oxindoles containing furopyrimidine or pyrrole, respectively, in moderate-to-good yields under relatively mild reaction conditions. Graphic abstract: A Brønsted acid-catalyzed reaction of 6-amino uracil, 1,3-dimethylbarbituric acid or ethyl 3-aminocrotonate
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12

Chen, Bo, Jiaheng Lei, and Junling Zhao. "Michael Addition of Aryl Thiols to 3-(2,2,2-Trifluoroethylidene)Oxindoles under Catalyst-Free Conditions: The Rapid Synthesis of Sulfur-Containing Oxindole Derivatives." Journal of Chemical Research 42, no. 4 (2018): 210–14. http://dx.doi.org/10.3184/174751918x15240724383170.

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A mild and efficient catalyst-free method for the rapid synthesis at room temperature of 3-thiomethylated oxindole derivatives has been achieved via the Michael addition of aryl thiols to ring and 1-substituted 3-(2,2,2-trifluoroethylidene)oxindoles in dichloromethane. The method was applicable to a wide range of thiols and variously substituted 3-(2,2,2-trifluoroethylidene)oxindoles under mild conditions as demonstrated by the synthesis in high yields with good diastereoselectivities of 30 3-thiomethylated oxindoles bearing a trifluoromethyl group.
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13

Jin, Qiao-Wen, Zhuo Chai, You-Ming Huang, Gang Zou та Gang Zhao. "Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts". Beilstein Journal of Organic Chemistry 12 (15 квітня 2016): 725–31. http://dx.doi.org/10.3762/bjoc.12.72.

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A highly enantioselective α-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by amino acids-derived chiral phosphine catalysts is reported. The corresponding products containing a tetrasubstituted carbon center attached to a nitrogen atom at the C-3 position of the oxindole were obtained in high yields and with up to 98% ee.
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14

Jiang, Yan, Min-Yi Tian, Xiong-Li Liu та ін. "Highly Diastereo-, α-Regioselective Catalyst-Free Construction of Adjacent Dispirobisoxindoles with Three Contiguous Quaternary Carbon Centers". Synthesis 51, № 03 (2018): 683–92. http://dx.doi.org/10.1055/s-0037-1610290.

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A new methodology was developed for the highly diastereoselective construction of dispirobisoxindole scaffolds via a domino α-regioselective Michael/cyclization reaction sequence of 3-isothiocyanato oxindoles and isatylidene malononitriles under catalyst-free conditions. Complex polycyclic oxindoles featuring two side-by-side oxindole skeletons and three contiguous quaternary carbon centers were synthesized in up to 95% yield and >20:1 dr. This protocol could provide libraries of stereochemically rich small molecules that will help in the search for new bioactive molecules.
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15

Palmieri, Alessandro, Marino Petrini, Elena Chiurchiù, and Federico Rossi. "Oxidative Conversion of Sulfonyl Indoles into 3-Alkylidene-2-oxindoles under Flow Chemical Conditions." Synthesis 50, no. 02 (2017): 371–76. http://dx.doi.org/10.1055/s-0036-1588584.

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Sulfonyl indoles were converted into 3-alkylidene-2-oxindoles using NCS as the sole reagent under flow chemical conditions. The conjugated oxindole derivatives were generally obtained as E stereoisomers in moderate to satisfactory yields. The transformation entails the oxidation of the indole ring by NCS followed by elimination of arylsulfinic acid in order to install the exocyclic unsaturation.
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16

Tiwari, Keshri Nath, and Chandran R. "Krapcho Dealkoxycarbonylation Strategy of Ethyl Cyanoacetate for the Synthesis of 3-Hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-Dicyanomethyl-2-oxindoles in a Reaction with Isatin." Synthesis 52, no. 15 (2020): 2233–40. http://dx.doi.org/10.1055/s-0040-1707816.

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A new strategy for the synthesis of 3-hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-dicyanomethyl-2-oxindoles in a reaction of isatin with ethyl cyanoacetate by Krapcho dealkoxycarbonylation reaction in aqueous media is demonstrated. The reaction provides an easy access to synthetically and medicinally valuable oxindole alkylnitriles in good to very good yields. Wider substrate scope and operationally simple experimental procedures are highlighted features of the developed protocol. Based on control experiments, a plausible mechanism of reaction and synergistic effect of water is also rationalize
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17

Connolly, Terrence J., and Tony Durst. "Metal hydride mediated reduction of 3-(alkylthio)oxindoles containing other potentially reducible groups." Canadian Journal of Chemistry 75, no. 5 (1997): 536–41. http://dx.doi.org/10.1139/v97-063.

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The reduction of several 3-(methylthio)oxindoles bearing ester groups on the benzene ring has been studied. The reaction is very dependent on the substitution of the oxindole, and the position of the ester group. Deprotonation of the C3 center by the metal hydride is the major initial pathway. This deprotonation plays a role in the reduction of the pendant ester group. Ester groups ortho, and presumably para, to C3 are very difficult to reduce, reaction only occurring with excess LiAlH4 at elevated temperatures. Once reduction starts, it is very difficult to stop, with reduction of the ester t
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18

Efremov, Alexander M., Olga V. Beznos, Roman O. Eremeev, et al. "Microwave-Assisted Synthesis of 3-Hydroxy-2-oxindoles and Pilot Evaluation of Their Antiglaucomic Activity." International Journal of Molecular Sciences 24, no. 6 (2023): 5101. http://dx.doi.org/10.3390/ijms24065101.

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Glaucoma is a widespread neurodegenerative disease for which increased intraocular pressure (IOP) is a primary modifiable risk factor. Recently, we have observed that compounds with oxindole scaffolds are involved in the regulation of intraocular pressure and therefore have potential antiglaucomic activity. In this article, we present an efficient method for obtaining novel 2-oxindole derivatives via microwave-assisted (MW) decarboxylative condensation of substituted isatins with malonic and cyanoacetic acids. Various 3-hydroxy-2-oxindoles were synthesized using MW activation for 5–10 min with
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19

Liu, Li, Yue Li, Tiao Huang, Dulin Kong, and Mingshu Wu. "A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids." Beilstein Journal of Organic Chemistry 17 (September 7, 2021): 2321–28. http://dx.doi.org/10.3762/bjoc.17.150.

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A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.
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20

Topanov, P. A., M. V. Dmitriev, S. Yu Balandina, Y. V. Shklyaev, I. V. Mashevskaya, and A. N. Maslivets. "Pseudo-three-component spiro[dihydrofuran-2,3′-oxindoles] synthesis: <i>in situ</i> generation of diazooxindole." Журнал общей химии 93, no. 11 (2023): 1680–89. http://dx.doi.org/10.31857/s0044460x23110057.

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Upon reaction with N -substituted pyrroloquinoxalinetriones, isatin hydrazone is oxidized to diazooxindole and enters into a formal [4+1] cycloaddition reaction with N -substituted pyrroloquinoxalinetriones to form compounds containing a spiro[dihydrofuran-2,3′-oxindole] fragment, which is interesting for medicinal chemistry. The reaction of diazooxindoles with N -unsubstituted pyrroloquinoxalinetriones afforded analogous substituted spiro[dihydrofuran-2,3′-oxindoles]. The resulting compounds have moderate antimicrobial activity.
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21

Dalpozzo, Renato, and Raffaella Mancuso. "Enantioselective Vinylogous Reactions of 3-Alkylidene Oxindoles." Synthesis 50, no. 13 (2018): 2463–72. http://dx.doi.org/10.1055/s-0037-1609731.

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Oxindoles represent an important class of bioactive compounds and synthetic derivatives found in many natural products. Most of these compounds are chiral molecules and the challenge of their asymmetric synthesis has fascinated many research groups. In particular, the creation of chiral centers out of the oxindole ring by vinylogous addition to 3-alkylidene-substituted oxindoles (3-alkylidene-1,3-dihydro-2H-indol-2-ones) has emerged in recent years. This review aims to give an overview of this topic.1 Introduction2 Aldol and Mannich Reactions3 Addition to Unsaturated Carbonyl Compounds4 Additi
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22

Ortega-Martínez, Aitor, Cynthia Molina, Cristina Moreno-Cabrerizo, José Sansano, and Carmen Nájera. "Synthesis of 3,3-Disubstituted 2-Oxindoles by Deacylative Alkylation of 3-Acetyl-2-oxindoles." Synthesis 49, no. 23 (2017): 5203–10. http://dx.doi.org/10.1055/s-0036-1590880.

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An innovative and efficient monoalkylation and nonsymmetrical 3,3-dialkylation of oxindoles has been achieved. First, the monoalkylation of 3-acetyl-2-oxindoles can be performed in good yields under mild reaction conditions using alkyl halides and benzyltrimethylammonium hydroxide (Triton B) as base at room temperature. This methodology is applied to construct the synthetically challenging compound 1,3-dimethyl-2-oxindole. Subsequent deacylative alkylation (DaA) of the alkylated 3-acetyl-2-oxindoles with alkyl halides takes place efficiently using LiOEt or by conjugate addition with electron-d
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23

Tokushige, Keisuke, Shota Asai, and Takumi Abe. "Molecular Iodine-Catalyzed Synthesis of 3,3-Disubstituted Isatins: Total Synthesis of Indole Alkaloid, 3,3-Dimethoxy-2-oxindole." Chemistry 7, no. 2 (2025): 43. https://doi.org/10.3390/chemistry7020043.

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3,3-Dialkoxy-2-oxindoles are prevalent in natural products and exhibit unique biological activities. Among them, acyclic alkoxy analogues show instability in acidic conditions, making access to acyclic isatin ketals highly challenging. Conventional methods for the synthesis of 3,3-dialkoxy-2-oxindoles usually require strongly acidic and harsh reaction conditions, resulting in a low overall efficiency. Herein, we report on an acid- and metal-free protocol for the synthesis of 3,3-dialkoxy-2-oxindoles from isatins through an iodine-catalyzed ketalization. This photochemical protocol does not req
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24

KONDO, YOSHIKAZU, YOJI MITADERA, and SHIGEO NOZOE. "Oxindoles. V. Selective Solvolysis Reactions of Oxindole-Spirodimer." YAKUGAKU ZASSHI 105, no. 8 (1985): 724–29. http://dx.doi.org/10.1248/yakushi1947.105.8_724.

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25

Mukhopadhyay, Chhanda, Sayan Pramanik, Suman Ray, Suvendu Maity та Prasanta Ghosh. "Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with In Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds". Synthesis 53, № 13 (2021): 2240–52. http://dx.doi.org/10.1055/a-1384-1967.

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AbstractAn efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindole derivatives. The procedure is based on the 1,3-dipolar character of the corresponding diazo compounds under base-catalyzed conditions. The method has a wide substrate scope and uses easily available starting materials.
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26

Tang, Ri-Yuan, Wen-Xu Zheng, Yan-Yan Liao та Li Xu. "Palladium-Catalyzed Selective Synthesis of 3-Hydroxy-2-oxindoles via Cascade C–H Cycloaddition and Oxidation of α-Aminoaceto­phenones". Synthesis 50, № 23 (2018): 4645–50. http://dx.doi.org/10.1055/s-0037-1610537.

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A novel method for the synthesis of 3-hydroxy-2-oxindole (3-hydroxyindolin-2-one) derivatives by palladium-catalyzed tandem C–H cycloaddition and oxidation of α-aminoacetophenone has been developed. In the presence of Pd(OAc)2 and AgOAc, a variety of 3-hydroxy-2-oxindoles were synthesized in moderate yields. Control experiments show that the selective cycloaddition occurs prior to the oxidation is crucial for this successful chemical transformation.
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27

Kumar, Nivesh, Santanu Ghosh, Subhajit Bhunia, and Alakesh Bisai. "Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds." Beilstein Journal of Organic Chemistry 12 (June 8, 2016): 1153–69. http://dx.doi.org/10.3762/bjoc.12.111.

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The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a ‘transition-metal-free’ intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon–carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.
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28

Lin, Yingjie, Haifeng Duan, Xin Zhang, Zhonglin Wei, Jungang Cao та Dapeng Liang. "Chiral Urea-Catalyzed Asymmetric Mannich Reaction of 3-Fluorooxindoles with α-Amidosulfones: Synthesis of Optically Active α-Fluoro-β-amino-oxindoles". Synlett 33, № 05 (2022): 488–94. http://dx.doi.org/10.1055/a-1747-2724.

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AbstractThe asymmetric Mannich reaction of 3-fluorooxindoles and α-amidosulfones catalyzed by a chiral urea catalyst derived from quinine in presence of K3PO4 was developed. Through the asymmetric reaction, a series of α-fluoro-β-amino-oxindoles, containing a tertiary carbon stereocenter, could be obtained in high yields (up to 95%) with high enantioselectivity (95%) and diastereoselectivity (&gt;99:1). Such α-fluoro-β-amino-oxindole compounds are expected to become candidates in the field of medicine.
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29

Yurino, Taiga, Takeshi Ohkuma, Hamdiye Ece, and Yuji Tange. "Silyl Cyanopalladate-Catalyzed Friedel–Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives." Synlett 32, no. 09 (2021): 935–39. http://dx.doi.org/10.1055/a-1373-7017.

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Abstract3-Aryloxindole derivatives were synthesized through a Friedel–Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc)2. Wide varieties of diethyl phosphates derived from N-arylmandelamides were converted almost quantitatively into oxindoles. When N,N-dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.
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30

Tingare, Yogesh S., Chaochin Su, Ming-Tai Shen, Sheng-Han Tsai, Shih-Yu Ho, and Wen-Ren Li. "New Oxindole-Bridged Acceptors for Organic Sensitizers: Substitution and Performance Studies in Dye-Sensitized Solar Cells." Molecules 25, no. 9 (2020): 2159. http://dx.doi.org/10.3390/molecules25092159.

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New D-π-A configured organic sensitizers featuring halogen-substituted oxindole-bridged acceptor units have been synthesized for dye-sensitized solar cells applications. Among fluorine, bromine, and iodine substitution, the cell based on bromine incorporated dye exhibited the highest efficiency. The oxindoles in these sensitizers were found to assist the electron injection through the chelation of their amide carbonyl groups to the TiO2 surface. This study provides an alternate approach for future rational dye design to gain excellent DSSC performance.
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31

Radul, Oleg, Natalia Sucman, Serghei Pogrebnoi, Alic Barba, Athina Geronikaki, and Fliur Macaev. "Synthesis and Antiviral Activity of New Thiazole, 1,2,4-Triazol and Oxindole Derivatives." Chemistry Journal of Moldova 6, no. 1 (2011): 101–9. http://dx.doi.org/10.19261/cjm.2011.06(1).03.

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The synthesis and antiviral activity evaluation of new derivatives of 2-aminothiazole, 1,2,4-triazole, as well as oxindoles has been realized. The synthesized compounds exhibited different cytotoxicity, in particular, oxindols 4, 5 , 7 , 8 , 9, 10, 11, 12, 13, 58 as well as thiazole/triazole 73 and 75 turned out to be the most cytotoxic for MT-4 cell lines. The compounds 11, 12, 73, and 75 are more toxic than reference compound Efavirenz. As far as the antiviral activity is concerned, none of the title compounds turned out active against Reo-1, Sb-1, VSV, RSV, YFV and VV viruses. The results o
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32

Suaad Mohammed Hussain and Zainab Abdul Zahraa. "Synthesis, characterization and antimicrobial activity of some new N-substituted-oxindole derivatives." Journal of Wasit for Science and Medicine 8, no. 3 (2022): 89–99. http://dx.doi.org/10.31185/jwsm.274.

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The aim of this research is the synthesis of new heterocyclic derivatives containing 4-oxo-thiazolidines, tetrazol or oxoazetidin ring from oxindole. To obtain these derivatives, oxindole [1] was chosen as the starting material to synthesize -chloro-N-oxindole acetamide [2] which was prepared by two methods. The first method by direct condensation of oxindole with chloroacetylchloride in presence of triethylamine and absolute ethanol as solvent. The second method by reaction of chloroacetylchloride with sodium salt of oxindole. Treatment of -chloro-N-oxindole acetamide [2] with hydrazine hyd
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33

Connolly, Terrence J., and Tony Durst. "Metal hydride mediated reduction of 1,3-dimethyl-3(methylthio)oxindole." Canadian Journal of Chemistry 75, no. 5 (1997): 542–46. http://dx.doi.org/10.1139/v97-064.

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The metal hydride mediated reduction of 4-carboethoxy-1,3-dimethyl-3-(methylthio)oxindole with lithium aluminum hydride and lithium triethylborohydride was studied. The results show that reduction of the oxindole carbonyl group is competitive with reduction of the pendant ester. The hemi-aminal that results from initial addition of hydride to the oxindole carbonyl may follow a number of reaction pathways, one of which is an unprecedented rearrangement. A mechanism is proposed that accounts for all observed products. Keywords: oxindole, reduction, rearrangement.
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34

Redondo, Alejandro, Gabriela Riego, and Olga Pol. "The Antinociceptive, Antioxidant and Anti-Inflammatory Effects of 5-Fluoro-2-Oxindole during Inflammatory Pain." Antioxidants 9, no. 12 (2020): 1249. http://dx.doi.org/10.3390/antiox9121249.

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Recent studies demonstrate that 5-fluoro-2-oxindole inhibits neuropathic pain but the antinociceptive actions of this drug and its effects on the plasticity, oxidative and inflammatory changes induced by peripheral inflammation as well as on the effects and expression of µ-opioid receptors (MOR) have not been evaluated. In C57BL/6 male mice with inflammatory pain provoked by the subplantar administration of complete Freund’s adjuvant (CFA), we evaluated: (1) the antinociceptive actions of 5-fluoro-2-oxindole and its reversion with the HO-1 inhibitor, tin protoporphyrin IX (SnPP); (2) the effec
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35

Singh, Kuldeep, Sourav Pramanik, Trevor A. Hamlin, Biplab Mondal, Dinabandhu Das, and Jaideep Saha. "Lewis acid catalyzed annulation of spirocyclic donor–acceptor cyclopropanes with exo-heterocyclic olefins: access to highly functionalized bis-spirocyclopentane oxindole frameworks." Chemical Communications 55, no. 49 (2019): 7069–72. http://dx.doi.org/10.1039/c9cc03393a.

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36

Kulkarni, Mukund G., Attrimuni P. Dhondge, Sanjay W. Chavhan, et al. "Total synthesis of (±)-coerulescine and (±)-horsfiline." Beilstein Journal of Organic Chemistry 6 (September 27, 2010): 876–79. http://dx.doi.org/10.3762/bjoc.6.103.

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37

Novikova, Daria, Tatyana Grigoreva, Vladislav Gurzhiy, and Vyacheslav Tribulovich. "Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis." International Journal of Molecular Sciences 24, no. 14 (2023): 11339. http://dx.doi.org/10.3390/ijms241411339.

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The biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, synthetic availability, and ease of modification. In particular, both kinase inhibitors and kinase activators can be found among 3-benzylidene oxindoles. In this work, we studied model compounds obtained via oxindole condensation with aldehydes and alkylphenones. These condensation products can exist i
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38

Patel, Pitambar, and Gongutri Borah. "Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C–H carbenoid functionalization." Chemical Communications 53, no. 2 (2017): 443–46. http://dx.doi.org/10.1039/c6cc08788d.

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The Ir(iii)-catalyzed intermolecular C–H annulations of acetanilide with diazotized Meldrum's acid furnished the oxindole derivative. Brief synthetic applications of the synthesized oxindole were also demonstrated.
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39

Bisht, Girish Singh, Akanksha M. Pandey, Moreshwar B. Chaudhari, et al. "Ru-Catalyzed dehydrogenative synthesis of antimalarial arylidene oxindoles." Organic & Biomolecular Chemistry 16, no. 39 (2018): 7223–29. http://dx.doi.org/10.1039/c8ob01852a.

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40

Liu, Yun, Zhou Sun, Song Li, Kuirong Xiang, Yuan Zhang, and Ying Li. "Mg(ClO4)2-promoted [4 + 3] cycloaddition of oxindole derivatives with conjugated dienes: concise synthesis of spirocycloheptane oxindole derivatives." RSC Advances 6, no. 32 (2016): 26954–58. http://dx.doi.org/10.1039/c6ra03259a.

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41

Jaiswal, Manish K., Bhuvnesh Singh, Shreemoyee De, Neetu Singh та Ravi P. Singh. "Stereoselective formal [3 + 3] annulation of 3-alkylidene-2-oxindoles with β,γ-unsaturated α-keto esters". Organic & Biomolecular Chemistry 18, № 48 (2020): 9852–62. http://dx.doi.org/10.1039/d0ob02046j.

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1,4-Diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3 + 3] cycloaddition reaction of 3-alkylidene-2-oxindole and β,γ-unsaturated α-keto esters under mild reaction conditions afforded the spirocyclohexene-oxindole with excellent diastereoselectivity.
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42

Prabhakaran, Perumal, and Perumal Rajakumar. "Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides." RSC Advances 10, no. 17 (2020): 10263–76. http://dx.doi.org/10.1039/c9ra10463a.

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Spiropyrrolidine-oxindole grafted and bis-spiropyrrolizidine-oxindole grafted macrocyles with triazole as a spacer unit have been achieved via regioselective and stereoselective intra and self-intermolecular [3 + 2] cycloaddition of azomethine ylides (click reaction).
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43

Cerchiaro, Giselle, and Ana Maria da Costa Ferreira. "Oxindoles and copper complexes with oxindole-derivatives as potential pharmacological agents." Journal of the Brazilian Chemical Society 17, no. 8 (2006): 1473–85. http://dx.doi.org/10.1590/s0103-50532006000800003.

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44

Rafati, Pouria, Jalal Jafarzade, Akbar Hoseinnejad, Asieh Khalilpour, Mojtaba Taghizadeh Armaki, and Firoozeh Kermani. "Investigating the Effectiveness of Spirocyclopropane-Oxindole Derivatives on Clinical Isolates of Candida albicans." Hormozgan Medical Journal 28, no. 1 (2024): 41–48. http://dx.doi.org/10.34172/hmj.8325.

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Objectives: Given the spread of azole resistance in Candida albicans (C. albicans), searching for new potent compounds, such as spirocyclopropane-oxindole derivatives is important. This study evaluates the antifungal susceptibility of spirocyclopropane-oxindole derivatives on clinical isolates of C. albicans. Methods: Antifungal susceptibility of 50 clinical isolates of C. albicans to spirocyclopropane-oxindole derivatives (4a, 4b, and 4c), nystatin, and fluconazole were evaluated according to Clinical Laboratory Standards Institute (M27-S4) guidelines. The medicinal dilution range of the comp
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45

Naganawa, Yuki, Tomotaka Aoyama, and Hisao Nishiyama. "Cu(ii)-catalyzed enantioselective oxygen atom transfer from oxaziridine to oxindole derivatives with chiral phenanthroline." Org. Biomol. Chem. 13, no. 47 (2015): 11499–506. http://dx.doi.org/10.1039/c5ob01840d.

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In the presence of a Cu(ii) complex of chiral, N,N,O-tridentate phenanthroline ligand (S)-2, asymmetric oxygen atom transfer of oxindole (3) using Davis’ oxaziridine (4) occurred to give the corresponding 3-aryl-3-hydroxy-2-oxindole derivatives (1) with excellent enantioselectivity.
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46

Nimmo, Alastair J., Kevin Kasten, George White та ін. "One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening". Molecules 29, № 15 (2024): 3635. http://dx.doi.org/10.3390/molecules29153635.

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Malamides (diamide derivatives of malic acid) are prevalent in nature and of significant biological interest, yet only limited synthetic methods to access functionalised enantiopure derivatives have been established to date. Herein, an effective synthetic method to generate this molecular class is developed through in situ formation of spirocyclic β-lactone-oxindoles (employing a known enantioselective isothiourea-catalysed formal [2+2] cycloaddition of C(1)-ammonium enolates and isatin derivatives) followed by a subsequent dual ring-opening protocol (of the β‑lactone and oxindole) with amine
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47

Witter, Ludwig, Timm Anke, and Olov Sterner. "A New Inhibitor of Synovial Phospholipase A2 from Fermentations of Penicillium Sp. 62-92." Zeitschrift für Naturforschung C 53, no. 1-2 (1998): 60–64. http://dx.doi.org/10.1515/znc-1998-1-212.

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AbstractPenidiamide, a new tripetide containing dehydrotryptamine, glycine and anthranilic acid linked together by two amide bonds, and oxindole were isolated from submerged cultures of Penicillium sp. 62-92 . Both compounds preferentially inhibited human synovial phospholipase A2, penidiamide with an IC50 of 30 μᴍ and oxindole of 380 μᴍ. With the exception of U 937 cells (leukemia, human), no cytotoxic activities were detected against HL-60- (leukemia, human), HeLa S3- (epitheloid carcinoma, human), BHK 21- (kidney fibroblasts, hamster), and L1210-cells (leukemia, mouse). No antimicrobial act
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48

Mohammed Sameer Abdul Shahed and Ahmed H. Mageed. "One-pot Multicomponent Synthesis and Biological Activity of Oxindole- linked Isatin Schiff Bases Derivatives." Journal of Kufa for Chemical Sciences 3, no. 2 (2024): 31–53. http://dx.doi.org/10.36329/jkcm/2024/v3.i2.12321.

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The study focuses on the synthesis of isatin- oxindole compounds through a two-step process. In the first step, using mannich reaction, new derivatives of Isatin are synthesized by reacting Isatin with either oxindole, along with formaldehyde. This reaction results in the formation of Isatin- oxindole derivative. In the second step, these Isatin derivatives are further reacted with various aniline derivatives to generate new compounds containing Isatin. The synthesized compounds are characterized using spectroscopic techniques such as FTIR, 1H NMR, and 13C NMR. The study also explores the biol
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49

Volkova, Maria S., Alexander M. Efremov, Elena N. Bezsonova, et al. "Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity." Molecules 27, no. 21 (2022): 7462. http://dx.doi.org/10.3390/molecules27217462.

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2,3-Dihydroindoles are promising agents for the synthesis of new compounds with neuroprotective and antioxidant properties. Usually, these compounds are obtained by direct reduction of the corresponding indoles containing acceptor groups in the indole ring for its activation. In this work, we propose a synthetic strategy to obtain new 2,3-dihydroindole derivatives from the corresponding polyfunctional 2-oxindoles. Three methods were proposed for reduction of functional groups in the 2-oxindole and 2-chloroindole molecules using various boron hydrides. The possibility of chemoselective reductio
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50

Lee, Hyun Ju, Sangku Lee, Jin Woo Lim, and Jae Nyoung Kim. "An Expedient Synthesis of Oxindole Dimers by Direct Oxidative Dimerization of Oxindoles." Bulletin of the Korean Chemical Society 34, no. 8 (2013): 2446–50. http://dx.doi.org/10.5012/bkcs.2013.34.8.2446.

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