71687-76-8Relevant academic research and scientific papers
Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines
Gopalaiah, Kovuru,Tiwari, Ankit
, p. 7229 - 7237 (2020/12/01)
A novel synthetic route for the construction of (E)-3-alkylideneindolin-2-ones through iron-catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self-condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3-alkylideneindolin-2-one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.
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.
Room-temperature palladium-catalyzed intramolecular oxidative aminocarbonylation of vinylic C(sp2)-H bonds with amines and CO
Yang, Xu-Heng,Li, Kai,Song, Ren-Jie,Li, Jin-Heng
supporting information, p. 616 - 623 (2014/02/14)
A new, mild route to access 3-methyleneindolin-2-ones is presented that proceeds through a room-temperature, palladium-catalyzed intramolecular oxidative aminocarbonylation of alkenes with amines and CO. This method represents a new aminocarbonylation str
Room-Temperature Palladium-Catalyzed Intramolecular Oxidative Aminocarbonylation of Vinylic C(sp2)-H Bonds with Amines and CO
Yang, Xu-Heng,Li, Kai,Song, Ren-Jie,Li, Jin-Heng
, p. 616 - 623 (2015/10/05)
A new, mild route to access 3-methyleneindolin-2-ones is presented that proceeds through a room-temperature, palladium-catalyzed intramolecular oxidative aminocarbonylation of alkenes with amines and CO. This method represents a new aminocarbonylation str
Diastereoselective access to tri-and pentacyclic spiro-γ-lactam- oxindole cores through a tandem aza-michael initiated ring closure sequence
Allous, Iyad,Comesse, Sebastien,Sanselme, Morgane,Daich, Adam
body text, p. 5303 - 5310 (2011/11/13)
Herein, we present a new development of the previously described aza-Michael-initiated ring closure (MIRC) process to access spirooxindole cores. The key spiro-cyclization step between various α-bromoacetamides and methyleneindolinones was efficient and tolerant of a wide range of functional groups. Yields and diastereoselectivities for the spirocyclization were usually high and furnished original spiro[oxindole-3,3′-γ-lactam] derivatives. The utility of these novel building blocks for the preparation of more sophisticated derivatives was demonstrated by the preparation of four pentacyclic spirooxindoles.
Palladium-catalyzed intramolecular 5-exo-dig hydroarylations of N-arylpropiolamides: Thermodynamics-controlled stereoselective synthesis of 3-methyleneoxindoles
Jiang, Tao-Shan,Tang, Ri-Yuan,Zhang, Xing-Guo,Li, Xin-Hua,Li, Jin-Heng
supporting information; experimental part, p. 8834 - 8837 (2010/03/02)
(Chemical Equation Presented) Palladium-catalyzed intramolecular hydroarylation of N-arylpropiolamides has been developed for the stereoselective synthesis of 3-(monosubstituted methylene)oxindoles. In the presence of Pd(OAc)2 and dppf, a varie
Heterobimetallic cobalt/rhodium nanoparticle-catalyzed carbonylative cycloaddition of 2-alkynylanilines to oxindoles
Park, Ji Hoon,Kim, Eunha,Chung, Young Keun
supporting information; experimental part, p. 4718 - 4721 (2009/05/31)
(Chemical Equation Presented) The cobalt-rhodium heterobimetallic nanoparticle-catalyzed synthesis of oxindoles from 2-alkynylanilines in the presence of carbon monoxide is described.
Stereoselective synthesis of 3-alkylideneoxindoles using tandem indium-mediated carbometallation and palladium-catalyzed cross-coupling reactions
Yanada, Reiko,Obika, Shingo,Kobayashi, Yusuke,Inokuma, Tsubasa,Oyama, Munetaka,Yanada, Kazuo,Takemoto, Yoshiji
, p. 1632 - 1642 (2007/10/03)
The first efficient methods for the stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles via radical cyclization reactions were investigated using tandem indium-mediated carbometallation and palladium-catalyzed cross-co
Stereoselective synthesis of 3-alkylideneoxindoles via palladium-catalyzed domino reactions
Yanada, Reiko,Obika, Shingo,Inokuma, Tsubasa,Yanada, Kazuo,Yamashita, Masayuki,Ohta, Shunsaku,Takemoto, Yoshiji
, p. 6972 - 6975 (2007/10/03)
We have developed efficient catalytic methods for the stereoselective and diversity synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles and 3-alkylidene-benzofuran-2-ones via palladium-catalyzed Heck/Suzuki-Miyaura, Heck/Heck, and Hec
Stereoselective synthesis of 3-alkylideneoxindoles using tandem in-mediated carbometalation and Pd-catalyzed cross-coupling reaction
Yanada, Reiko,Obika, Shingo,Oyama, Munetaka,Takemoto, Yoshiji
, p. 2825 - 2828 (2007/10/03)
Efficient methods for stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles were investigated using tandem In-mediated carbometalation and ligandless Pd-catalyzed coupling reaction.
