Metal-free oxidative acylation/cyclization of N-methacryloyl-2-phenylbenzoimidazole with aryl aldehydes: an easy access to benzimidazo[2,1-a]isoquinolin-6(5H)-ones

A metal-free radical cyclization strategy has been developed for the synthesis of fused benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives from N-methacryloyl-2-arylbenzoimidazole and aryl aldehydes using 70% tert-butylhydroperoxide in water (TBHP). The reaction proceeds through a sequential acyl r...

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Published inOrganic & biomolecular chemistry Vol. 17; no. 44; pp. 9627 - 9630
Main Authors Boora, Ramesh, Kumar, G. Ravi, Reddy, B. V. Subba
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.11.2019
Royal Society of Chemistry
Subjects
Acylation
Aldehydes
Aromatic compounds
Chemistry
Chemistry, Organic
Free radicals
Metals
Physical Sciences
Science & Technology
ALKENES
TBHP
CATALYZED SYNTHESIS
ALKYLATION
N-ARYLACRYLAMIDES
CARBONYL
ALIPHATIC-ALDEHYDES
ALKYNES
DERIVATIVES
GREEN
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Summary:A metal-free radical cyclization strategy has been developed for the synthesis of fused benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives from N-methacryloyl-2-arylbenzoimidazole and aryl aldehydes using 70% tert-butylhydroperoxide in water (TBHP). The reaction proceeds through a sequential acyl radical addition/cyclization strategy. This method is useful for the generation of biologically relevant tetracyclic scaffolds in a single-step process.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01979k