Palladium-Catalyzed One-Pot Synthesis of 5-(1-Arylvinyl)-1H-benzimidazoles: Overcoming the Limitation of Acetamide Partners

被引：22

作者：

Naret, Timothee ^{[1
]}

Retailleau, Pascal ^{[2
]}

Bignon, Jerome ^{[2
]}

Brion, Jean-Daniel ^{[1
]}

Alami, Mouad ^{[1
]}

Hamze, Abdallah ^{[1
]}

机构：

[1] Univ Paris 11, Chim Therapeut Lab, Equipe Labellisee Ligue Canc, Fac Pharm,CNRS,LabEx LERMIT,BioCIS UMR 8076, 5 Rue JB Clement, F-92296 Chatenay Malabry, France

[2] CNRS, Lab Inst Chim Subst Nat, UPR 2301, Ave Terrasse, F-91198 Gif Sur Yvette, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 11期

关键词：

benzimidazoles; hydrazones; olefination; one-pot reaction; palladium; CARBENE MIGRATORY INSERTION; N-TOSYLHYDRAZONES; ANTINEOPLASTIC AGENTS; CYCLIZATION; REAGENTS; HYDRAZONES;

D O I：

10.1002/adsc.201600173

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new one-pot palladium-catalyzed process between N-tosylhydrazones, N-(dihalophenyl)-imidates, and amines was designed. This reaction involves Barluenga cross-coupling and N-arylation followed by cyclization to produce functionalized benzimidazoles. During this transformation, one CC bond and two CN bonds were created by a single palladium-catalyzed reaction. Depending on the starting materials, a library of 5-(1-arylvinyl)-1H-benzimidazoles was synthesized. Among several arylvinylbenzimidazole derivatives evaluated, one compound exhibits excellent antiproliferative activity in the nanomolar concentration range against human colon carcinoma cell lines (HCT-116) and human lung adenocarcinoma epithelial cell lines (A549).

引用

页码：1833 / 1847

页数：15

共 40 条

[1]

[Anonymous], 2007, Angew. Chem

[2]

[Anonymous], PHARM RES

[3] Copper-Catalyzed Coupling of N-Tosylhydrazones with Amines: Synthesis of Fluorene Derivatives [J].