Reaction of Isatin and 2-Chloropyridinium Salt: An Efficient and Diastereoselective Synthesis of α,β-Unsaturated Oxindoles

被引：0

作者：

Imani, Kaveh ^{[1
]}

Shirazi, Hamideh ^{[1
]}

Golchin, Golnaz ^{[1
]}

Bazgir, Ayoob ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Dept Organ Chem, Tehran 1983969411, Iran

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 19期

关键词：

INHIBITORS; DESIGN; INDOLINONES; PYRIDONE; KINASE;

D O I：

10.1021/acs.joc.4c01069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, mild, and diastereoselective method has been developed for the synthesis of beta-pyridone-alpha,beta-unsaturated oxindoles by the reaction of isatins and 2-chloropyridinium salts in EtOH at room temperature for 5 min. This method operates under mild reaction conditions, providing the product with a good yield and diastereoselectivity, and it exhibits excellent tolerance toward various functional groups. The predominant isomer is the Z isomer, which can convert to the E isomer in the presence of NaN3.

引用

页码：13937 / 13946

页数：10

共 50 条

[31] ZrCl4 Catalysed Diastereoselective Synthesis of Spirocarbocyclic Oxindoles via [4+2] Cycloaddition
Kumar, Kapil
Siddique, Julekha
Gangar, Mukesh
Goyal, Sandeep
Rawal, Ravindra K.
Nair, Vipin A.
CHEMISTRYSELECT, 2016, 1 (10): : 2409 - 2412
[32] Synthesis of chiral spiro-cyclopentene/cyclopentadiene-oxindoles through an asymmetric [3+2] cycloaddition of isatin-derived MBH carbonates and β,γ-unsaturated α-keto esters
Chen, Yu
Cui, Bao-Dong
Bai, Mei
Han, Wen Yong
Wan, Nan-Wei
Chen, Yong-Zheng
TETRAHEDRON, 2019, 75 (21) : 2971 - 2979
[33] A convenient E-diastereoselective synthesis of NH-isatin N ?-arylimines via the aza-Wittig reaction
Filatov, Vadim E.
Iuzabchuk, Dmitrii A.
Tarasevich, Boris N.
Zyk, Nikolai ., V
Beloglazkina, Elena K.
MENDELEEV COMMUNICATIONS, 2022, 32 (05) : 634 - 636
[34] A SIMPLE DIASTEREOSELECTIVE SYNTHESIS OF 2',3'-UNSATURATED ARYL C-GLUCOPYRANOSIDES
CASIRAGHI, G
CORNIA, M
RASSU, G
ZETTA, L
FAVA, GG
BELICCHI, MF
TETRAHEDRON LETTERS, 1988, 29 (27) : 3323 - 3326
[35] A SHORT AND EFFICIENT DIASTEREOSELECTIVE SYNTHESIS OF 2'-SUBSTITUTED 2-CYCLOPROPYLGLYCINES
ZINDEL, J
DEMEIJERE, A
SYNTHESIS-STUTTGART, 1994, (02): : 190 - 194
[36] Efficient synthesis of 3-arylaminopyrroline-2-ones by the tandem reaction of anilines and β,γ-unsaturated α-ketoesters
Wu, Yan-Chao
Liu, Li
Wang, Dong
Chen, Yong-Jun
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (04) : 949 - 955
[37] Efficient Synthesis of Polysubstituted Tetrahydrothiopyran Sulfoxides by the Reaction of α,β-Unsaturated Ketones and Na2S
Chen, Dong-Dong
Wang, Nai-Xing
Lan, Xing-Wang
Zhang, Wei
Bai, Cui-Bing
Geng, Hui-Ling
Zhou, Le
Li, Yi-He
CURRENT ORGANIC SYNTHESIS, 2016, 13 (04) : 651 - 655
[38] The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives
Farago, Tuende
Remete, Attila M. M.
Szatmari, Istvan
Ambrus, Rita
Palko, Marta
RSC ADVANCES, 2023, 13 (28) : 19356 - 19365
[39] An Efficient Synthesis of Fused Polycyclic Indole Derivatives via Aldol-Hetero Diels-Alder Reaction of α,β-Unsaturated Thio-oxindoles with Various Dienophiles
Moghaddam, F. Matloubi
Taheri, S.
Hojabri, L.
Pirani, P.
Maktabian, S.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2011, 8 (01) : 265 - 271
[40] Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles
Zhang, Qing-Bao
Jia, Wen-Liang
Ban, Yong-Liang
Zheng, Yong
Liu, Qiang
Wu, Li-Zhu
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (08) : 2595 - 2598

← 1 2 3 4 5 →