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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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