28864-72-4Relevant articles and documents
Electrochemical Rearrangement of 3-Hydroxyoxindoles into Benzoxazinones
Vayer, Marie,Pastor, Miryam,Kofink, Christiane,Maulide, Nuno
supporting information, p. 27 - 32 (2022/01/15)
We report an unexpected rearrangement of 3-hydroxyoxindoles into benzoxazinones using electrochemistry. Our reaction employs mild and environmentally friendly conditions, and the benzoxazinone products are obtained in moderate to excellent yields. Mechanistic experiments suggest that a peroxide intermediate is likely involved.
One-Pot Synthesis of 2-Aminobenzophenones from 2-Alkynyl Arylazides Catalyzed by Pd and Cu Precursors
Fan, Hui,Xu, Shijie,Yang, Fan,Zhang, Xiaoxiang,Zhao, Xuechun
supporting information, p. 4555 - 4558 (2021/08/30)
We describe a novel one-pot three-step reaction of 2-alkynyl arylazides through palladium-catalyzed formation of 3-hydroxy-3-phenylindolin-2-ones followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to give 2-aminobenzophenones. This synthetic method works well with various 2-alkynyl arylazides and affords the products in moderate to good yields under mild reaction conditions.
One-pot synthesis of 3-hydroxy-2-oxindoles: Via acyloin rearrangements of 2-hydroxy-indolin-3-ones generated in situ from 2-alkynyl arylazides
Zhou, Zhiqiang,Xu, Yao,Zhu, Boyu,Li, Ping,Hu, Guiwen,Yang, Fan,Xu, Shijie,Zhang, Xiaoxiang
supporting information, p. 20303 - 20307 (2020/12/21)
A novel one-pot method to prepare 3-hydroxy-2-oxindoles via acyloin rearrangements of 2-hydroxy-indolin-3-ones generated in situ from 2-alkynyl arylazides has been described. The reaction was accomplished to afford a variety of 3-hydroxy-2-oxindole derivatives in moderate to good yields under mild conditions. This journal is
Organocatalytic stereoselective conjugate addition of 3-substituted oxindoles with in situ generated ortho-quinone methides
Liang, Weihong,Yin, Wenhao,Wang, Tingzhong,Qiu, Fayang G.,Zhao, Junling
supporting information, p. 1742 - 1747 (2018/04/02)
A novel method for the stereoselective conjugate addition of 3-substituted oxindoles to in situ generated o-QMs was described. This process was catalyzed efficiently by a cinchonidine-derived squaramide catalyst in oil-water phase, furnishing the corresponding 3,3-disubsituted oxindole derivatives in moderate to high yields (up to 98%) with high stereoselectivities (up to 95% ee, 15.4:1 dr). The utility of this reaction was also investigated by the gram-scale synthesis and derivatization of one of the products.
N-heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation of oxindoles with aryl chlorides and aerobic oxidation of the products in a one-pot procedure
Xiao, Zheng-Kang,Yin, Hui-Ying,Shao, Li-Xiong
, p. 1254 - 1257 (2013/04/23)
NHC-Pd(II)-Im complex 1 was found to be an effective catalyst for the α-arylation of unprotected oxindoles with aryl chlorides to give products 4 in 44-98% yields under a N2 atmosphere. Furthermore, if the reactions were first performed under conditions identical to those for the α-arylation reaction for 12 h and then exposed to air for another 3 h, 3-aryl-3-hydroxy-2-oxindoles 5 can be obtained in 49-84% yields in a one-pot procedure.
Facile synthesis of enantioenriched Cγ-tetrasubstituted α-amino acid derivatives via an asymmetric nucleophilic addition/protonation cascade
Duan, Shu-Wen,An, Jing,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information; scheme or table, p. 2290 - 2293 (2011/06/22)
Chemical equations presented. An asymmetric nucleophilic addition/protonation reaction of 3-substituted oxindoles and ethyl 2-phthalimidoacrylate has been described. This strategy can give direct access to Cγ-tetrasubstituted α-amino acid derivatives bearing 1,3-nonadjacent stereocenters with up to 98% yield, 94:6 dr, and >99% ee. Dual activation is proposed in the transition state, and the opposite enantiomers can be obtained simply by changing cinchonidine-derived catalyst to the cinchonine analogue.
Lewis acid-catalyzed enantioselective hydroxylation reactions of oxindoles and β-keto esters using DBFOX ligand
Ishimaru, Takehisa,Shibata, Norio,Nagai, Jun,Nakamura, Shuichi,Toru, Takeshi,Kanemasa, Shuji
, p. 16488 - 16489 (2007/10/03)
The first catalytic enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2-oxindoles using the DBFOX-Zn(II) complex, leading to pharmaceutically important chiral 3-hydroxy-2-oxindoles was described. The structure of oxidant was found to play
Rhodium-catalyzed addition of arylboronic acids to isatins: An entry to diversity in 3-aryl-3-hydroxyoxindoles
Toullec, Patrick Y.,Jagt, Richard B. C.,De Vries, Johannes G.,Feringa, Ben L.,Minnaard, Adriaan J.
, p. 2715 - 2718 (2007/10/03)
A general method for the catalytic 1,2-addition of aryl and alkenyl boronic acids to isatins is described using a rhodium(I)/triphenylphosphite catalyst. The application of this transformation allows the synthesis of a variety of 3-aryl-3-hydroxyoxindole
