Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo[4,5]imidazo[1,2-a]pyridines and benzo[4,5]imidazo[2,1-a]isoquinolines

Byeong Woo Yang; Pham Duy Quang Dao; Nam Sik Yoon; Chan Sik Cho

doi:10.1016/j.jorganchem.2017.09.025

Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo[4,5]imidazo[1,2-a]pyridines and benzo[4,5]imidazo[2,1-a]isoquinolines

Byeong Woo Yang
, Pham Duy Quang Dao
, Nam Sik Yoon
, Chan Sik Cho

Department of Applied Chemistry

Kyungpook National University

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

2-(2-Bromovinyl)benzimidazoles are coupled and cyclized with 1,3-diketones in DMF in the presence of a catalytic amount of copper(I) iodide and a base to afford the corresponding benzo[4,5]imidazo[1,2-a]pyridines in moderate yields. 2-(2-Bromoaryl)benzimidazoles also react with 1,3-diketones under similar reaction conditions to give benzo[4,5]imidazo[2,1-a]isoquinolines in similar yields.

Original language	English
Pages (from-to)	136-142
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	851
DOIs	https://doi.org/10.1016/j.jorganchem.2017.09.025
State	Published - 2017

Keywords

1,3-Diketones
Benzo[4,5]imidazo[1,2-a]pyridines
Benzo[4,5]imidazo[2,1-a]isoquinolines
Copper catalyst
Heterocycles

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10.1016/j.jorganchem.2017.09.025

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@article{4146505b09854aac806a27bd0bc37557,

title = "Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo[4,5]imidazo[1,2-a]pyridines and benzo[4,5]imidazo[2,1-a]isoquinolines",

abstract = "2-(2-Bromovinyl)benzimidazoles are coupled and cyclized with 1,3-diketones in DMF in the presence of a catalytic amount of copper(I) iodide and a base to afford the corresponding benzo[4,5]imidazo[1,2-a]pyridines in moderate yields. 2-(2-Bromoaryl)benzimidazoles also react with 1,3-diketones under similar reaction conditions to give benzo[4,5]imidazo[2,1-a]isoquinolines in similar yields.",

keywords = "1,3-Diketones, Benzo[4,5]imidazo[1,2-a]pyridines, Benzo[4,5]imidazo[2,1-a]isoquinolines, Copper catalyst, Heterocycles",

author = "Yang, \{Byeong Woo\} and \{Quang Dao\}, \{Pham Duy\} and Yoon, \{Nam Sik\} and Cho, \{Chan Sik\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier B.V.",

year = "2017",

doi = "10.1016/j.jorganchem.2017.09.025",

language = "English",

volume = "851",

pages = "136--142",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Copper-catalyzed C-C coupling and cyclization

T2 - Synthesis of benzo[4,5]imidazo[1,2-a]pyridines and benzo[4,5]imidazo[2,1-a]isoquinolines

AU - Yang, Byeong Woo

AU - Quang Dao, Pham Duy

AU - Yoon, Nam Sik

AU - Cho, Chan Sik

PY - 2017

Y1 - 2017

N2 - 2-(2-Bromovinyl)benzimidazoles are coupled and cyclized with 1,3-diketones in DMF in the presence of a catalytic amount of copper(I) iodide and a base to afford the corresponding benzo[4,5]imidazo[1,2-a]pyridines in moderate yields. 2-(2-Bromoaryl)benzimidazoles also react with 1,3-diketones under similar reaction conditions to give benzo[4,5]imidazo[2,1-a]isoquinolines in similar yields.

AB - 2-(2-Bromovinyl)benzimidazoles are coupled and cyclized with 1,3-diketones in DMF in the presence of a catalytic amount of copper(I) iodide and a base to afford the corresponding benzo[4,5]imidazo[1,2-a]pyridines in moderate yields. 2-(2-Bromoaryl)benzimidazoles also react with 1,3-diketones under similar reaction conditions to give benzo[4,5]imidazo[2,1-a]isoquinolines in similar yields.

KW - 1,3-Diketones

KW - Benzo[4,5]imidazo[1,2-a]pyridines

KW - Benzo[4,5]imidazo[2,1-a]isoquinolines

KW - Copper catalyst

KW - Heterocycles

UR - https://www.scopus.com/pages/publications/85029869203

U2 - 10.1016/j.jorganchem.2017.09.025

DO - 10.1016/j.jorganchem.2017.09.025

M3 - Article

AN - SCOPUS:85029869203

SN - 0022-328X

VL - 851

SP - 136

EP - 142

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo[4,5]imidazo[1,2-a]pyridines and benzo[4,5]imidazo[2,1-a]isoquinolines

Abstract

Keywords

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