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Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano- and Furanoquinolines Catalyzed by 4-Nitrophthalic Acid

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Summary.

4-Nitrophthalic acid was found to be an effective catalyst for the imino Diels-Alder reaction of N-benzylideneanilines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran to afford pyrano- and furanoquinolines in good yields. It was also found that aryl amines react smoothly with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under the same condition to afford the corresponding pyrano- and furanoquinolines in high yields. This catalyst is inexpensive, easily available, water soluble, and stable to aqueous reaction conditions.

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Authors and Affiliations

  1. Department of Post Graduate Studies and Research in Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta, Karnataka, India

    Aswathanarayana Srinivasa & Kittappa Malavalli Mahadevan

  2. Department of Studies in Chemistry, Karnatak University, Karnataka, India

    Kallappa Mahadevappa Hosamani

  3. BioOrganics and Applied Materials Pvt. Ltd., Bangalore, India

    Vijaykumar Hulikal

Authors
  1. Aswathanarayana Srinivasa
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  2. Kittappa Malavalli Mahadevan
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  3. Kallappa Mahadevappa Hosamani
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  4. Vijaykumar Hulikal
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Correspondence to Kittappa Malavalli Mahadevan.

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Srinivasa, A., Mahadevan, K., Hosamani, K. et al. Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano- and Furanoquinolines Catalyzed by 4-Nitrophthalic Acid. Monatsh Chem 139, 141–145 (2008). https://doi.org/10.1007/s00706-007-0765-4

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  • DOI: https://doi.org/10.1007/s00706-007-0765-4

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