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

[1] CONVENIENT METHOD FOR PREPARATION OF ISOTHIOCYANATES USING 2-CHLOROPYRIDINIUM SALT
SHIBANUMA, T
SHIONO, M
MUKAIYAMA, T
CHEMISTRY LETTERS, 1977, (05) : 573 - 574
[2] CONVENIENT METHOD FOR PREPARATION OF CARBODIIMIDES USING 2-CHLOROPYRIDINIUM SALT
SHIBANUMA, T
SHIONO, M
MUKAIYAMA, T
CHEMISTRY LETTERS, 1977, (05) : 575 - 576
[3] Fluorous 2-chloropyridinium salt (Mukaiyama condensation reagent) for amide formation reactions
Nagashima, T
Lu, YM
Petro, MJ
Zhang, W
TETRAHEDRON LETTERS, 2005, 46 (38) : 6585 - 6588
[4] A Novel and Efficient Isocyanide-Catalyzed Addition Reaction of Enaminones to Isatin Derivatives for Oxindoles Synthesis
Ali, Elham
Naimi-Jamal, Mohammad Reza
Rashid, Zahra
Ghahremanzadeh, Ramin
POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (04) : 1157 - 1168
[5] A SIMPLE HUCKEL APPROACH TO INTRAMOLECULAR PHOTOCYCLIZATION REACTION OF N-(2-CHLOROBENZYL)-PYRIDINIUM, N-(BENZYL)-2-CHLOROPYRIDINIUM, AND N-(2-CHLOROBENZYL)-2-CHLOROPYRIDINIUM SALTS
LEE, GH
PARK, YT
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1994, 15 (10) : 857 - 860
[6] Synthesis of 1-(1-aroyl-2-arylvinyl)-2-dicyanomethylen-1,2-dihydropyridines from 2-chloropyridinium salts and unsaturated nitriles
Khoroshilov G.E.
Chemistry of Heterocyclic Compounds, 2001, 37 (9) : 1141 - 1144
[7] A CONVENIENT METHOD FOR THE PREPARATION OF N,N'-DISUBSTITUTED THIOUREAS USING 2-CHLOROPYRIDINIUM SALT, SODIUM TRITHIOCARBONATE AND AMINES
TAKIKAWA, Y
INOUE, N
SATO, R
TAKIZAWA, S
CHEMISTRY LETTERS, 1982, (05) : 641 - 642
[8] Highly diastereoselective synthesis of trifluoromethyl containing spiro [pyrrolidin-3,2′-oxindoles] from N-2,2,2-trifluoroethylsubstituted isatin imines and β,γ-unsaturated α-keto esters
Xiong, Ya
Han, Xiao-Xue
Lu, Yu
Wang, Hui-Juan
Zhang, Min
Liu, Xiong-Wei
TETRAHEDRON, 2021, 87
[9] Ethylbenzene Hydroperoxide: An efficient oxidizing agent for diastereoselective synthesis of Spiroepoxy oxindoles
Valmiki, Praveen K.
Banyangala, Mohan
Varughese, Sunil
Somappa, Sasidhar B.
TETRAHEDRON LETTERS, 2022, 108
[10] Synthesis of α-Aryl-oxindoles via Grignard Reaction with Isatin in the Presence of Diphenyl Phosphite
Zhang, Xinxin X.
Wang, Pengkai K.
Zhang, Songlin L.
CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (13)

← 1 2 3 4 5 →