Base/DMSO-Promoted Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines via C−C Bond Formation

Seong Weon Lee; Pham Duy Quang Dao; Ho Jin Lim; Chan Sik Cho

doi:10.1002/adsc.202301365

Base/DMSO-Promoted Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines via C−C Bond Formation

Seong Weon Lee, Pham Duy Quang Dao, Ho Jin Lim, Chan Sik Cho

Kyungpook National University

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

2 Scopus citations

Abstract

In this study, a synthetic method to access benzo[4,5]imidazo[2,1-a]isoquinolines is developed by the reaction of 2-(2-bromoaryl)benzimidazoles with 1,3-diketones under basic conditions. A reaction pathway involving the initial formation of a C−C coupled intermediate by nucleophilic aromatic substitution and subsequent deacylative cyclocondensation is proposed for this process.

Original language	English
Pages (from-to)	1182-1188
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	366
Issue number	5
DOIs	https://doi.org/10.1002/adsc.202301365
State	Published - 8 Mar 2024

Keywords

Basic condition
Cyclization
C−C Bond formation
N-Fused heterocycles
Nucleophilic aromatic substitution

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title = "Base/DMSO-Promoted Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines via C−C Bond Formation",

abstract = "In this study, a synthetic method to access benzo[4,5]imidazo[2,1-a]isoquinolines is developed by the reaction of 2-(2-bromoaryl)benzimidazoles with 1,3-diketones under basic conditions. A reaction pathway involving the initial formation of a C−C coupled intermediate by nucleophilic aromatic substitution and subsequent deacylative cyclocondensation is proposed for this process.",

keywords = "Basic condition, Cyclization, C−C Bond formation, N-Fused heterocycles, Nucleophilic aromatic substitution",

author = "Lee, \{Seong Weon\} and Dao, \{Pham Duy Quang\} and Lim, \{Ho Jin\} and Cho, \{Chan Sik\}",

note = "Publisher Copyright: {\textcopyright} 2024 Wiley-VCH GmbH.",

year = "2024",

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doi = "10.1002/adsc.202301365",

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T1 - Base/DMSO-Promoted Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines via C−C Bond Formation

AU - Lee, Seong Weon

AU - Dao, Pham Duy Quang

AU - Lim, Ho Jin

AU - Cho, Chan Sik

PY - 2024/3/8

Y1 - 2024/3/8

N2 - In this study, a synthetic method to access benzo[4,5]imidazo[2,1-a]isoquinolines is developed by the reaction of 2-(2-bromoaryl)benzimidazoles with 1,3-diketones under basic conditions. A reaction pathway involving the initial formation of a C−C coupled intermediate by nucleophilic aromatic substitution and subsequent deacylative cyclocondensation is proposed for this process.

AB - In this study, a synthetic method to access benzo[4,5]imidazo[2,1-a]isoquinolines is developed by the reaction of 2-(2-bromoaryl)benzimidazoles with 1,3-diketones under basic conditions. A reaction pathway involving the initial formation of a C−C coupled intermediate by nucleophilic aromatic substitution and subsequent deacylative cyclocondensation is proposed for this process.

KW - Basic condition

KW - Cyclization

KW - C−C Bond formation

KW - N-Fused heterocycles

KW - Nucleophilic aromatic substitution

UR - https://www.scopus.com/pages/publications/85182832614

U2 - 10.1002/adsc.202301365

DO - 10.1002/adsc.202301365

M3 - Article

AN - SCOPUS:85182832614

SN - 1615-4150

VL - 366

SP - 1182

EP - 1188

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 5

ER -

Base/DMSO-Promoted Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines via C−C Bond Formation

Abstract

Keywords

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