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

[21] Highly diastereoselective cascade [5 + 1] double Michael reaction, a route for the synthesis of spiro(thio)oxindoles
Firouz Matloubi Moghaddam
Vahid Saberi
Ashkan Karimi
Scientific Reports, 11
[22] Povarov Reaction of β-Enamino Esters and Isatin-3-imines for Diastereoselective Synthesis of Spiro[indoline-3,2′-quinolines]
Gao, Hong
Sun, Jing
Yan, Chao-Guo
SYNTHESIS-STUTTGART, 2014, 46 (04): : 489 - 495
[23] Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3-Hydroxyamino-2-Oxindoles Using Nitrosoarenes
Shen, Ke
Liu, Xiaohua
Wang, Gang
Lin, Lili
Feng, Xiaoming
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (20) : 4684 - 4688
[24] Highly diastereoselective conjugate addition of nitroalkanes to α,β-unsaturated sugar lactones for the efficient synthesis of chiral 2-pyrrolidones
Li, Yan-Ping
Li, Zhong-Jun
Meng, Xiang-Bao
CARBOHYDRATE RESEARCH, 2011, 346 (13) : 1801 - 1808
[25] Highly diastereoselective cascade [5+1] double Michael reaction, a route for the synthesis of spiro(thio)oxindoles
Moghaddam, Firouz Matloubi
Saberi, Vahid
Karimi, Ashkan
SCIENTIFIC REPORTS, 2021, 11 (01)
[26] Lewis Acid Promoted Highly Diastereoselective Petasis Borono-Mannich Reaction: Efficient Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids
Li, Yi
Xu, Ming-Hua
ORGANIC LETTERS, 2012, 14 (08) : 2062 - 2065
[27] Efficient reaction pathway for the synthesis of saturated and mono-unsaturated 2-alkylcyclobutanones
Miesch, M
Miesch, L
Horvatovich, P
Burnouf, D
Delincée, H
Hartwig, A
Raul, F
Werner, D
Marchioni, E
RADIATION PHYSICS AND CHEMISTRY, 2002, 65 (03) : 233 - 239
[28] Thiourea-catalyzed asymmetric domino Michael-cyclization reaction of 3-isothiocyanato oxindoles with β,γ-unsaturated α-keto esters for the synthesis of spirocyclic oxindoles
Bai, Mei
Chen, Yong-Zheng
Cui, Bao-Dong
Xu, Xiao-Ying
Yuan, Wei-Cheng
TETRAHEDRON, 2019, 75 (14) : 2155 - 2161
[29] General strategy for the synthesis of unsaturated carbasugars via a diastereoselective seleno-Michael/aldol reaction
Banachowicz, Piotr
Buda, Szymon
RSC ADVANCES, 2025, 15 (07) : 5159 - 5166
[30] Stereoselective synthesis of 3-amino-2-oxindoles from isatin imines: new scaffolds for bioactivity evaluation
Kaur, Jasneet
Chimni, Swapandeep Singh
Mahajan, Suhel
Kumar, Akshay
RSC ADVANCES, 2015, 5 (65) : 52481 - 52496

← 1 2 3 4 5 →