15379-45-0Relevant academic research and scientific papers
Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols
Dambatta, Mubarak B.,Polidano, Kurt,Northey, Alexander D.,Williams, Jonathan M. J.,Morrill, Louis C.
, p. 2345 - 2349 (2019/05/16)
A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50–92 % yield, 79 % average yield).
Enabling CO Insertion into o-Nitrostyrenes beyond Reduction for Selective Access to Indolin-2-one and Dihydroquinolin-2-one Derivatives
Yang, Li,Shi, Lijun,Xing, Qi,Huang, Kuo-Wei,Xia, Chungu,Li, Fuwei
, p. 10340 - 10348 (2018/10/20)
The transition metal-catalyzed reductive cyclization of o-nitrostyrene in the presence of carbon monoxide (CO) has been developed to be a general synthetic route to an indole skeleton, wherein CO was used as a reductant to deoxidize nitroarene into nitrosoarene and/or nitrene with CO2 release, but the selective insertion of CO into the heterocyclic product with higher atom economy has not yet been realized. Herein, the Pd-catalyzed reduction of o-nitrostyrene by CO and its regioselective insertion were efficiently achieved to produce synthetically useful five- and six-membered benzo-fused lactams. Detailed investigations revealed that the chemoselectivity to indole or lactam was sensitive to the nature of the counteranions of Pd2+ precursors, whereas ligands significantly decided the carbonylative regioselectivity by different reaction pathways. Using PdCl2/PPh3/B(OH)3 (condition A), an olefin hydrocarboxylation was primarily initiated followed by partial reduction of the NO2 moiety and cyclization reaction to give N-hydroxyl indolin-2-one, which was further catalytically reduced by CO to afford the indolin-2-one as the final product with up to 95% yield. When the reaction was conducted under the Pd(TFA)2/BINAP/TsOH·H2O system (condition B), complete deoxygenation and carbonylation of the NO2 group occurred initially to yield the corresponding isocyanate followed by internal hydrocyclization to generate 3,4-dihydroquinolin-2-one with up to 98% yield. Importantly, the methodology could be efficiently applied in the synthesis of marketed drug Aripiprazole.
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
Magnesium-Catalyzed Electrophilic Trifluoromethylation: Facile Access to All-Carbon Quaternary Centers in Oxindoles
Katayev, Dmitry,Kajita, Harutake,Togni, Antonio
supporting information, p. 8353 - 8357 (2017/06/28)
The first example of a magnesium-catalyzed direct trifluoromethylation of 3-substituted oxindoles using an electrophilic hypervalent iodine reagent is reported. The reaction proceeds under unprecedented mild conditions leading to the formation of an all-carbon quaternary center in oxindoles in high chemical yield and demonstrates excellent functional group tolerance. In addition to trifluoromethyl, other perfluoroalkyl groups can be introduced with similar level of efficacy. Mechanistic investigations are consistent with the involvement of a radical pathway. The chemical versatility of the obtained products is further illustrated through their conversion in situ into valuable organofluorine building blocks, making the protocol more widely applicable.
Evaluation of 3-ethyl-3-(phenylpiperazinylbutyl)oxindoles as PET ligands for the serotonin 5-HT7 receptor: Synthesis, pharmacology, radiolabeling, and in vivo brain imaging in pigs
Herth, Matthias M.,Andersen, Valdemar L.,Hansen, Hanne D.,Stroth, Nikolas,Volk, Balázs,Lehel, Szabolcs,Dyssegaard, Agnete,Ettrup, Anders,Svenningsson, Per,Knudsen, Gitte M.,Kristensen, Jesper L.
supporting information, p. 3631 - 3636 (2015/05/05)
We have investigated several oxindole derivatives in the pursuit of a 5-HT7 receptor PET ligand. Herein the synthesis, chiral separation, and pharmacological profiling of two possible PET candidates toward a wide selection of CNS-targets are de
Regiodivergent access to five- and six-membered benzo-fused lactams: Ru-catalyzed olefin hydrocarbamoylation
Li, Bin,Park, Yoonsu,Chang, Sukbok
, p. 1125 - 1131 (2014/02/14)
We report herein a new strategy of the Ru-catalyzed intramolecular olefin hydrocarbamoylation for the regiodivergent synthesis of five- and six-membered benzo-fused lactams starting from N-(2-alkenylphenyl)formamides. Using a combined catalyst of Ru3
Optimization of (arylpiperazinylbutyl)oxindoles exhibiting selective 5-HT7 receptor antagonist activity
Volk, Balázs,Gacsályi, István,Pallagi, Katalin,Poszávácz, László,Gy?n?s, Ildikó,Szabó, éva,Bakó, Tibor,Spedding, Michael,Simig, Gyula,Szénási, Gábor
scheme or table, p. 6657 - 6669 (2011/12/02)
A series of (arylpiperazinylbutyl)oxindoles as highly potent 5-HT 7 receptor antagonists has been studied for their selectivity toward the 5-HT1A receptor and α1-adrenoceptor. Several derivatives exhibited high 5-HT7
C-3 alkylation of oxindole with alcohols catalyzed by an indene-functionalized mesoporous iridium catalyst
Liu, Guohua,Huang, Tianzeng,Zhang, Yuli,Liang, Xiaohui,Li, Yunsheng,Li, Hexing
experimental part, p. 655 - 659 (2012/01/12)
A heterogeneous indene-based iridium catalyst with a highly ordered dimensional-hexagonal mesostructure was prepared through complexation of IrCl3 with the indene-functionalized SBA-15 silica materials. During C-3 alkylation of oxindole with va
Iridium catalysed C-3 alkylation of oxindole with alcohols under solvent free thermal or microwave conditions
Grigg, Ronald,Whitney, Simon,Sridharan, Visuvanathar,Keep, Ann,Derrick, Andrew
experimental part, p. 4375 - 4383 (2009/10/17)
Ir-catalysed alkylation of oxindole and N-methyl oxindole with a range of substituted benzyl and heteroaryl alcohols under solvent free thermal or microwave conditions afforded the corresponding C-3-monoalkylated products in high to excellent yield.
Direct N-carbamoylation of 3-monosubstituted oxindoles with alkyl imidazole carboxylates
Trost, Barry M.,Zhang, Yong,Zhang, Ting
supporting information; experimental part, p. 5115 - 5117 (2009/10/24)
(Chemical Equation Presented) Regioselective N-carbamoylation of oxindoles was achieved through the use of imidazole carboxylate reagents. This reaction provides ready access to N-carbamoyl-3-monosubstituted oxindoles.
