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

Author:

Lee Seong Weon1ORCID,Dao Pham Duy Quang1ORCID,Lim Ho‐Jin2,Cho Chan Sik1ORCID

Affiliation:

1. Department of Applied Chemistry Kyungpook National University 80 Daehakro Bukgu Daegu 41566 Republic of Korea

2. Department of Environmental Engineering Kyungpook National University 80 Daehakro Bukgu Daegu 41566 Republic of Korea

Abstract

AbstractIn 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.

Publisher

Wiley

Subject

General Chemistry

Reference95 articles.

1. For reviews of N-fused heterocycles see:

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3. A. F. Pozharskii A. T. Soldatenkov A. R. Katritzky inHeterocycles in Life and Society: An Introduction to Heterocyclic Chemistry Biochemistry and Applications 2nd ed. John Wiley & Sons 2011;

4. J. Alvarez-Builla J. J. Vaquero inModern Heterocyclic Chemistry Wiley-VHC Weinheim 2011;

5. T. Eicher S. Hauptmann A. Speicher inThe Chemistry of Heterocycles: Structure Reactions Synthesis and Applications 3rd ed. Wiley-VHC Weinheim 2012.

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