Transition metal-free construction of trinuclear N-fused hybrid scaffolds by double nucleophilic aromatic substitution under microwave irradiation

Treatment of 2-(2-bromoaryl)- and 2-(2-bromovinyl)benzimidazoles with 2-aminoazoles in the presence of a base under microwave irradiation triggers double C(sp 2 )-N coupling to form trinuclear N-fused hybrid scaffolds. A reaction pathway involving nucleophilic aromatic substitution (S N Ar) accompan...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 21; no. 24; pp. 659 - 6593
Main Authors Dao, Pham Duy Quang, Lim, Ho-Jin, Cho, Chan Sik
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2019
Royal Society of Chemistry
Subjects
Ammonia
Benzimidazoles
Chemistry
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Green chemistry
Irradiation
Physical Sciences
Scaffolds
Science & Technology
Science & Technology - Other Topics
Substitution reactions
Transition metals
AZOLE
AMINES
BENZIMIDAZOLE-4,7-DIONES
ARYLATION
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Summary:Treatment of 2-(2-bromoaryl)- and 2-(2-bromovinyl)benzimidazoles with 2-aminoazoles in the presence of a base under microwave irradiation triggers double C(sp 2 )-N coupling to form trinuclear N-fused hybrid scaffolds. A reaction pathway involving nucleophilic aromatic substitution (S N Ar) accompanied by ammonia evolution is proposed as a key step of this transition metal-free process. A green construction of trinuclear N-fused hybrid scaffolds by transition metal-free double C(sp 2 )-N coupling of 2-(2-bromoaryl)- and 2-(2-bromovinyl)benzimidazoles with 2-aminoazoles under microwave irradiation has been developed.
Bibliography:10.1039/c9gc03410b
Electronic supplementary information (ESI) available. See DOI
ISSN:1463-9262
1463-9270
DOI:10.1039/c9gc03410b