Ru(II)-Catalyzed [4 + 2]-Annulation of 2‑Alkenyl/Arylimidazoles with N-Substituted Maleimides and 1,4-Naphthoquinones: Access to Imidazo-Fused Polyheterocycles

Synthesis of imidazo-fused polyheterocyclic molecular frameworks, viz. imidazo­[1,2-a]­pyrrolo­[3,4-e]­pyridines, imidazo­[2,1-a]­pyrrolo­[3,4-c]­isoquinolines, and benzo­[g]­imidazo­[1,2-a]­quinoline-6,11-diones, has been achieved by the ruthenium­(II)-catalyzed [4 + 2] C–H/N–H annulation of 2-alke...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 89; no. 4; pp. 2272 - 2282
Main Authors Meena, Neha, Nipate, Dhananjay S., Swami, Prakash N., Rangan, Krishnan, Kumar, Anil
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.02.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CASCADE
ACTIVATION
ALKYNE ANNULATION
HETEROCYCLES
C-H FUNCTIONALIZATION
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Summary:Synthesis of imidazo-fused polyheterocyclic molecular frameworks, viz. imidazo­[1,2-a]­pyrrolo­[3,4-e]­pyridines, imidazo­[2,1-a]­pyrrolo­[3,4-c]­isoquinolines, and benzo­[g]­imidazo­[1,2-a]­quinoline-6,11-diones, has been achieved by the ruthenium­(II)-catalyzed [4 + 2] C–H/N–H annulation of 2-alkenyl/2-arylimidazoles with N-substituted maleimides and 1,4-naphthoquinones. The developed protocol is operationally simple, exhibits broad substrate scope with excellent functional group tolerance, and provides the desired products in moderate to good yields. The mechanistic studies suggest that the reaction involves the formation of a C–C bond through Ru-catalyzed C­(sp2)–H bond activation followed by intramolecular cyclization.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02229