14003-19-1Relevant articles and documents
E,Z Isomerization Studies of Ethyl 2-Oxo-3-Indolinylidenecyanoacetates by 1H NMR Spectroscopy
Morales-Rios, Martha S.,Mora-Perez, Yolanda,Joseph-Nathan, Pedro
, p. 1153 - 1157 (1992)
The kinetics of base-catalysed E/Z isomerization for a series of ethyl 2-oxo-3-indolinylidenecyanoacetates in CDCl3 solutions were studied by 1H NMR spectroscopy.Both polarizable double bond considerations and steric requirements of the base must be considered in explaining the results.The E/Z equilibrium of ethyl 1-carbethoxy-2-oxo-3-indolinylidenecyanoacetate was reached faster than those of ethyl 2-oxo-3-indolinylidenecyanoacetate and the 1-methyl derivative by a factor of ca. 10 in the presence of triethylamine, and the isomerization were faster when quinuclidine was used.In pure DMSO-d6 solutions, the equilibria were established upon dissolution, but addition of small amounts of acid slowed the isomerization process in these systems.Key words: E/Z isomerization, 1H NMR, Ethyl-2-oxo-3-indolinylidenecyanoacetates
An expeditious access of 2,5′-dioxo-5′,6′,7′,8′-tetrahydro-1′H-spiro[indoline-3,4′-quinoline]-3′-carboxylate by reaction of isatin, ethyl cyanoacetate and enaminone in water
Tiwari, Keshri Nath,Prabhakaran,Kumar, Vaneet,Rajendra, Thakar Snehal,Mathew, Shintu
, p. 3596 - 3601 (2018)
We have demonstrated three component reaction of isatin, enaminone and ethyl cyanoacetate leading to sprirooxindole scaffold without catalyst in water. The synthetic protocol has several advantages like wide substrate scope, atom-economy and operationally simple experimental procedures which provides rapid access to library of compounds. The mechanistic details of the reaction has been investigated during the course of study.
Iron-catalyzed cross-dehydrogenative coupling of indolin-2-ones with active methylenes for direct carbon-carbon double bond formation
Tan, Zhi-Yu,Wu, Ke-Xin,Huang, Lu-Shan,Wu, Run-Shi,Du, Zheng-Yu,Xu, Da-Zhen
supporting information, p. 332 - 335 (2020/02/13)
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.
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
Shi, Taoda,Teng, Shenghan,Wei, Yajie,Guo, Xin,Hu, Wenhao
supporting information, p. 4936 - 4940 (2019/09/30)
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.
Copper-catalyzed hydroboration of alkenyl oxindoles
Contreira, Maria Eduarda,Lüdtke, Diogo S.,Moro, Angélica V.
supporting information, p. 2784 - 2787 (2018/06/18)
Herein we describe the NHC-Cu(I)-catalyzed hydroboration of alkenyl oxindoles. The corresponding boronates were obtained in good yields, under operationally simple and environmentally friendly conditions, using ethanol as the solvent. Our studies revealed that water-based systems were not very effective. Furthermore, the obtained products are amenable to further elaboration and can be useful to the synthesis of a broader range of oxindole-containing molecules with biological relevance.
Ionic Liquid Mediated Green Synthesis of Spirooxindoles from N-methyl Quinolones and Their Anti Bacterial Activity
Bhupathi, Raja S.,Madhu, Bandi,Reddy, Ch. Venkata Ramana,Devi, B. Rama,Dubey
, p. 2326 - 2332 (2017/07/25)
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.
Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast
Rossetti, Arianna,Sacchetti, Alessandro,Bonfanti, Marta,Roda, Gabriella,Rainoldi, Giulia,Silvani, Alessandra
, p. 4584 - 4590 (2017/07/11)
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
TiCl4/DMAP mediated: Z -selective knovenagel condensation of isatins with nitroacetates and related compounds
Zhu, Luyi,Yan, Peipei,Zhang, Lvye,Chen, Zhangtao,Zeng, Xiaofei,Zhong, Guofu
, p. 51352 - 51358 (2017/11/15)
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.
Bioreduction of the C=C double bond with Pseudomonas monteilii ZMU-T17: One approach to 3-monosubstituted oxindoles
Zhao, Jia,Guan, Shuicheng,Zhou, Xiaojian,Han, Wenyong,Cui, Baodong,Chen, Yongzheng
, p. 3098 - 3104 (2016/05/19)
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.
Knovenagel condensation of isatin with nitriles and 1, 3-diketones
Riyaz,Indrasena,Naidu,Dubey
, p. 120 - 123 (2014/02/14)
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
