Metal-free selective synthesis of 2-substituted benzimidazoles catalyzed by Bronsted acidic ionic liquid: Convenient access to one-pot synthesis of N-alkylated 1,2-disubstituted benzimidazoles

被引：46

作者：

Senapak, Warapong ^{[1
,2
]}

Saeeng, Rungnapha ^{[1
,2
]}

Jaratjaroonphong, Jaray ^{[1
,2
]}

Promarak, Vinich ^{[3
]}

Sirion, Uthaiwan ^{[1
,2
]}

机构：

[1] Burapha Univ, Fac Sci, Dept Chem, Sangsook 20131, Chonburi, Thailand

[2] Burapha Univ, Fac Sci, Ctr Excellence Innovat Chem, Sangsook 20131, Chonburi, Thailand

[3] Vidyasirimedhi Inst Sci & Technol VISTEC, Sch Mol Sci & Engn, Wangchan 21210, Rayong, Thailand

来源：

TETRAHEDRON | 2019年 / 75卷 / 26期

关键词：

2-Substituted benzimidazole; N-Alkylated 1,2-disubstituted benzimidazole; Metal-free condition; Acidic ionic liquid; Condensation reaction; VITRO ANTIMICROBIAL ACTIVITY; LIGHT-EMITTING-DIODES; MANNICH REACTION; BENZOXAZOLE DERIVATIVES; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; GREEN SYNTHESIS; PIEZOCHROMIC LUMINESCENCE; BIOLOGICAL EVALUATION; AROMATIC-COMPOUNDS;

D O I：

10.1016/j.tet.2019.05.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel efficient method for the selective synthesis of 2-substituted benzimidazoles is described through condensation reaction of o-phenylenediamines with a wide rang of aliphatic, aromatic and heteroaromatic aldehyde substrates using Bronsted acidic ionic liquid as a reusable catalyst under metal-free conditions at ambient temperature. Notably, Dodecylimidazolium hydrogen sulfate ([Dodeclm][HSO4]) is the most efficient catalyst for good to excellent yields of the corresponding products (up to 98%). Subsequently, this protocol was successfully applied for the preparation of N-alkylated 1,2-disubstituted benzimidazoles in high to excellent yields via sequential one-pot reaction. In addition, catalysts are recycled at least four times without significant loss in activity. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：3543 / 3552

页数：10

共 119 条

[51] Synthesis of 1,3-Dialkyl-1,2,3-triazolium Ionic Liquids and Their Applications to the Baylis-Hillman Reaction [J].