Ruthenium-catalyzed C3 Alkylation of the Furan/Thiophene Ring in 2-(Furan-2-carbonyl)/(Thiophene-2-carbonyl)-1-methylimidazoles with Acrylic Acid Derivatives

被引：0

作者：

Shepelenko, K. E. ^{[1
]}

Gnatiuk, I. G. ^{[1
]}

Chernyshev, V. M. ^{[1
]}

机构：

[1] Platov South Russian State Polytech Univ NPI, Novocherkassk 346428, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 60卷 / 11期

基金：

俄罗斯科学基金会;

关键词：

ruthenium; C-H alkylation; furan; thiophene; aroylimidazoles; C-H BOND; CARBOXYLIC-ACIDS; C3-ALKYLATION; ALKENYLATION; ACRYLATES;

D O I：

10.1134/S1070428024110071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the synthesis of 3-alkyl-2-(furan-2-carbonyl)/(thiophene-2-carbonyl)-1-methylimidazoles by the ruthenium-catalyzed selective C3 alkylation of the furan or thiophene ring in 2-(furan-2-carbonyl)/(thiophene-2-carbonyl)-1-methylimidazoles with acrylic acid esters, amides, or nitrile has been developed. The resulting compounds may be of interest as polyfunctional reagents for preparing 3-(2-carboxyethyl)furan/thiophene-2-carboxylic acid derivatives.

引用

页码：2140 / 2146

页数：7

共 34 条

[1] Olanzapine for schizophrenia [J].

Duggan, L ;

Fenton, M ;

Rathbone, J ;

Dardennes, R ;

El-Dosoky, A ;

Indran, S .

COCHRANE DATABASE OF SYSTEMATIC REVIEWS, 2005, (02)

[2] Recent progress of sulphur-containing high-efficiency organic light-emitting diodes (OLEDs) [J].

Feng, Zijun ;

Cheng, Zhuang ;

Jin, Haixu ;

Lu, Ping .

JOURNAL OF MATERIALS CHEMISTRY C, 2022, 10 (12) :4497-4520

[3] Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners [J].

Forgione, Pat ;

Brochu, Marie-Christine ;

St-Onge, Miguel ;

Thesen, Kris H. ;

Bailey, Murray D. ;

Bilodeau, Francois .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) :11350-11351

[4] Strategic Utilization of Multifunctional Carbene for Direct Synthesis of Carboxylic-Phosphinic Mixed Anhydride from CO2 [J].

Hoshimoto, Yoichi ;

Asada, Takahiro ;

Hazra, Sunit ;

Kinoshita, Takuya ;

Sombut, Panukorn ;

Kumar, Ravindra ;

Ohashi, Masato ;

Ogoshi, Sensuke .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (52) :16075-16079

[5] Late-Stage C-H Functionalization of Azines [J].

Josephitis, Celena M. ;

Nguyen, Hillary M. H. ;

McNally, Andrew .

CHEMICAL REVIEWS, 2023, 123 (12) :7655-7691

[6] Catalytic C-H Functionalization of Unreactive Furan Cores in Bio-Derived Platform Chemicals [J].

Karlinskii, Bogdan Y. ;

Ananikov, Valentine P. .

CHEMSUSCHEM, 2021, 14 (02) :558-568

[7] Recent advances in the development of green furan ring-containing polymeric materials based on renewable plant biomass [J].

Karlinskii, Bogdan Ya. ;

Ananikov, Valentine P. P. .

CHEMICAL SOCIETY REVIEWS, 2023, 52 (02) :836-862

[8] Base-Promoted Amidation and Esterification of Imidazolium Salts via Acyl C-C bond Cleavage: Access to Aromatic Amides and Esters [J].

Karthik, Shanmugam ;

Muthuvel, Karthick ;

Gandhi, Thirumanavelan .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02) :738-751

[9] Furan monomers and polymers from renewable plant biomass [J].

Kashparova, Vera P. ;

Chernysheva, Daria, V ;

Klushin, Victor A. ;

Andreeva, Veronika E. ;

Kravchenko, Oleg A. ;

Smirnova, Nina, V .

RUSSIAN CHEMICAL REVIEWS, 2021, 90 (06) :750-784

[10] Ruthenium(II)-catalyzed switchable C3-alkylation versus alkenylation with acrylates of 2-pyridylbenzofurans via C-H bond activation [J].

Kommagalla, Yadagiri ;

Mullapudi, Venkanna Babu ;

Francis, Fredi ;

Ramana, Chepuri V. .

CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (01) :114-117

← 1 2 3 4 →