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Regioselective O-alkylation: synthesis of 1-{2-[(2-chloroquinolin-3-yl)methoxy]-6-chloro-4-phenylquinolin-3-yl}ethanones

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Abstract

An efficient and regioselective O-alkylation of amides with a variety of electrophiles in the presence of silver nanoparticles is reported as part of our recent research on building blocks for synthesis of natural products. The nano-silver catalyst initiates O-alkylation of the amides by heteroalkyl halides. Reaction of equimolar 3-acetyl-6-chloro-4-phenylquinolin-2(1H)-one and 2-chloro-3-(chloromethyl)quinolines in the presence of silver nanoparticles in DMSO solution under reflux condition leads to the formation of 1-{1-[2-chloroquinolin-3-yl)methoxy]-6-chloro-4-phenylquinolin-3-yl}ethanones.

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Acknowledgments

This study was supported by Department of Science and Technology Government of India (grant no. SR/FTP/CS-99/2006). We also acknowledge IISc, Bangalore, for providing the NMR facility.

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Authors and Affiliations

  1. Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, 632 014, Tamil Nadu, India

    Machhindra Gund, S. Mohana Roopan, Fazlur-Rahman Nawaz Khan,  Rajesh Kumar & A. Sudheer Kumar

  2. Division of High Technology Materials Research, KBSI, Busan, 618 230, South Korea

    Fazlur-Rahman Nawaz Khan & Jong Sung Jin

Authors
  1. Machhindra Gund
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  2. S. Mohana Roopan
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  3. Fazlur-Rahman Nawaz Khan
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  4. Jong Sung Jin
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  5. Rajesh Kumar
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  6. A. Sudheer Kumar
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Correspondence to Fazlur-Rahman Nawaz Khan.

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Gund, M., Mohana Roopan, S., Nawaz Khan, FR. et al. Regioselective O-alkylation: synthesis of 1-{2-[(2-chloroquinolin-3-yl)methoxy]-6-chloro-4-phenylquinolin-3-yl}ethanones. Res Chem Intermed 38, 1111–1118 (2012). https://doi.org/10.1007/s11164-011-0447-z

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  • DOI: https://doi.org/10.1007/s11164-011-0447-z

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