59225-18-2Relevant academic research and scientific papers
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.
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
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
Three-component synthesis of spiro[indoline-3,4'-pyrano[3,2-b]pyran]-2,8'- diones using a one-pot reaction
Rahmati, Abbas,Khalesi, Zahra,Kenarkoohi, Tahmineh
, p. 132 - 140 (2014/03/21)
A one-pot, three-component reaction of an isatin and kojic acid with an active methylene compound such as ethyl cyanoacetate, methyl cyanoacetate and malononitrile in methanol using catalytic amount of DABCO to give 2'- amino-6'-(hydroxymethyl)-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-2, 8'-diones in good to excellent yields under reflux conditions, is described.
Phosphorus-containing Lewis base catalyzed highly regioselective cyclization of isatin derived electron-deficient alkenes with but-3-yn-2-one
Lian, Zhong,Wei, Yin,Shi, Min
supporting information; experimental part, p. 2401 - 2408 (2012/04/10)
In this paper, we reported that phosphorus-containing Lewis bases catalyzed [4+2] cyclization of N-protected isatin derived electron-deficient alkenes with but-3-yn-2-one could proceed smoothly to give the corresponding dihydropyrano[2,3-b]indoles in good
Synthesis of 2,6′-dioxo-1′,5′,6′,7′- tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-5′- carbonitriles via a one-pot, three-component reaction in water
Rahmati, Abbas,Kenarkoohi, Tahmineh,Khavasi, Hamid Reza
, p. 657 - 664 (2013/02/25)
A one-pot, three-component condensation reaction of an isatin, aminopyrazole, and alkyl cyanoacetate in water to give 2,6′-dioxo- 1′,5′,6′,7′-tetrahydrospiro[indoline-3, 4′-pyrazolo[3,4-b]pyridine]-5′-carbonitrile with good yields, at 90 C, using a Et3N as catalyst, is described.
Reaction of isatins with active methylene compounds on neutral alumina: Formation of knoevenagel condensates and other interesting products
Chakrabarty, Manas,Mukherjee, Ratna,Arima, Shiho,Harigaya, Yoshihiro
scheme or table, p. 139 - 149 (2009/05/07)
Isatin and its N-methyl and 5-nitro derivatives underwent smooth reaction with a variety of acyclic and cyclic active methylene compounds on neutral alumina at rt to efficiently furnish Knoevenagel condensates in the majority of the cases and tandem Knoevenagel condensation-Michael addition products including spiro compounds in two cases.
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
Abdelhamid, Ismail A.,Mohamed, Mona H.,Abdelmoniem, Amr M.,Ghozlan, Said A.S.
experimental part, p. 10069 - 10073 (2010/02/27)
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
