Highly regioselective C-5 alkynylation of imidazoles by one-pot sequential bromination and Sonogashira cross coupling

被引：9

作者：

Bellina, Fabio ^{[1
]}

Lessi, Marco ^{[1
]}

Marianetti, Giulia ^{[2
]}

Panattoni, Alessandro ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56194 Pisa, Italy

[2] Scuola Normale Super Pisa, I-56126 Pisa, Italy

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 25期

关键词：

Imidazoles; Sonogashira reaction; Regioselectivity; Aromatic bromination; Alkynylation; AZOLE DERIVATIVES; HETEROCYCLES; HALOALKYNES; ARYLATION; CATALYST;

D O I：

10.1016/j.tetlet.2015.04.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of 2-substituted 5-alkynyl-1H-imidazoles were easily prepared by a one-pot sequential procedure involving a highly regioselective electrophilic C-5 bromination of 1,2-dimethyl-1H-imidazole, 2-chloro-1-methyl-1H-imidazole, and 2-aryl-1-methyl-1H-imidazoles, followed by an efficient palladium/copper co-catalyzed Sonogashira-type alkynylation. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：3855 / 3857

页数：3

共 31 条

[1] Imidazole analogues of resveratrol: synthesis and cancer cell growth evaluation [J].

Bellina, Fabio ;

Guazzelli, Nicola ;

Lessi, Marco ;

Manzini, Chiara .

TETRAHEDRON, 2015, 71 (15) :2298-2305

[2] Mild Palladium-Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate [J].

Bellina, Fabio ;

Lessi, Marco ;

Manzini, Chiara .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) :5621-5630

[3] Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2009, 65 (50) :10269-10310

[4] NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles [J].

Chelucci, Giorgio ;

Figus, Susanna .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 393 :191-209

[5]

Chianelli D., 2010, [No title captured], Patent No. [WO2010/127152, 2010127152]

[6] Recent advances in Sonogashira reactions [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121

[7] ANTIVIRAL ACTIVITIES OF 5-ETHYNYL-1-BETA-D-RIBOFURANOSYLIMIDAZOLE-4-CARBOXAMIDE AND RELATED-COMPOUNDS [J].

DECLERCQ, E ;

COOLS, M ;

BALZARINI, J ;

SNOECK, R ;

ANDREI, G ;

HOSOYA, M ;

SHIGETA, S ;

UEDA, T ;

MINAKAWA, N ;

MATSUDA, A .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1991, 35 (04) :679-684

[8] Copper-catalyzed arene C-H bond cross-coupling [J].

Do, Hien-Quang ;

Daugulis, Olafs .

CHEMICAL COMMUNICATIONS, 2009, (42) :6433-6435

[9] Formal Inverse Sonogashira Reaction: Direct Alkynylation of Arenes and Heterocycles with Alkynyl Halides [J].

Dudnik, Alexander S. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) :2096-2098

[10] Copper-Catalyzed Intermolecular Oxidative Cyclization of Haloalkynes: Synthesis of 2-Halo-substituted Imidazo[1,2-a]pyridines, Imidazo[1,2-a]pyrazines and Imidazo[1,2-a]pyrimidines [J].

Gao, Yang ;

Yin, Meizhou ;

Wu, Wanqing ;

Huang, Huawen ;

Jiang, Huanfeng .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) :2263-2273

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