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One-Pot Synthesis of Novel Quinoline-Fused Azeto[1,2-a]benzimidazole Analogs Via Intramolecular Pd-Catalyzed C–N Coupling

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Abstract

A common strategy to incorporate four-membered ring system between benzimidazole and quinoline cores was developed by one-pot protocol involving the condensation of o-phenylenediamine with 2-chloroquinoline-3-carbaldehyde derivatives followed by intramolecular palladium catalyzed C–N coupling. A series of ligands, palladium sources, bases and solvents were screened to optimize the reaction conditions for the synthesis of quinoline-fused azeto[1,2-a]benzimidazoles.

Graphical Abstract

An efficient catalytic system for the introduction of 4-membered-ring system between benzimidazole and quinoline cores has been developed by one-pot intramolecular C–N coupling of o-phenylenediamine with 6-substituted-2-chloroquinoline-3-carbaldehydes.

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Acknowledgments

The authors are thankful to Director, S. V. National Institute of Technology, Surat for the scholarship, encouragement and facilities. We are also grateful to SAIF Punjab University, SDPARC, Kim and Centre of Excellence, Vapi, Gujarat, India, for providing necessary analytical support.

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Authors and Affiliations

  1. Department of Applied Chemistry, S. V. National Institute of Technology, Surat, 395007, India

    Amit B. Patel & Premlata Kumari

  2. Department of Chemistry, School of Science, Gujarat University, Ahmedabad, 380009, India

    Kishor H. Chikhalia

Authors
  1. Amit B. Patel
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  2. Premlata Kumari
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  3. Kishor H. Chikhalia
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Corresponding author

Correspondence to Kishor H. Chikhalia.

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Patel, A.B., Kumari, P. & Chikhalia, K.H. One-Pot Synthesis of Novel Quinoline-Fused Azeto[1,2-a]benzimidazole Analogs Via Intramolecular Pd-Catalyzed C–N Coupling. Catal Lett 144, 1332–1338 (2014). https://doi.org/10.1007/s10562-014-1266-9

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  • DOI: https://doi.org/10.1007/s10562-014-1266-9

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