Get access

One-Pot Synthesis of 1,3,5-Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1-Phenyl-2-propyn-1-ones in Pressurized Hot Water in the Absence of Added Catalysts

Authors

  • Makoto Tanaka,

    1. College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575 (Japan), Fax: : (+47)-474-2579
    Search for more papers by this author
  • Kazuya Nakamura,

    1. College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575 (Japan), Fax: : (+47)-474-2579
    Search for more papers by this author
  • Tatsuya Iwado,

    1. College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575 (Japan), Fax: : (+47)-474-2579
    Search for more papers by this author
  • Dr. Toshiyuki Sato,

    1. College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575 (Japan), Fax: : (+47)-474-2579
    Search for more papers by this author
  • Dr. Masaki Okada,

    1. College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575 (Japan), Fax: : (+47)-474-2579
    Search for more papers by this author
  • Dr. Kiwamu Sue,

    1. Nanosystem Research Institute, National Institute of Advanced Industrial Science and Technology, Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565 (Japan)
    Search for more papers by this author
  • Prof. Dr. Hiizu Iwamura,

    Corresponding author
    1. College of Science and Technology, Nihon University, 1-8-14 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-8308 (Japan), Fax: (+3)-3259-0468
    • College of Science and Technology, Nihon University, 1-8-14 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-8308 (Japan), Fax: (+3)-3259-0468
    Search for more papers by this author
  • Prof. Dr. Toshihiko Hiaki

    Corresponding author
    1. College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575 (Japan), Fax: : (+47)-474-2579
    • College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575 (Japan), Fax: : (+47)-474-2579
    Search for more papers by this author

Abstract

Cyclotrimerization of 1-phenyl-2-propyn-1-one in pressurized hot water gave 1,3,5-tribenzoylbenzene in one pot in 65 % yield after 7 min at 200 °C, or in 74 % yield after 60 min at 150 °C. The reaction did not take place in the absence of water, and added base promoted the reaction at 250 °C, suggesting a mechanism of three-consecutive Michael addition reactions. The reaction rates increased with temperature, but the yield of 1,3,5-tribenzoylbenzene decreased at the expense of formation of acetophenone as a side product at higher temperatures. p-Methyl and p-chloro-substituents on the phenyl ring retarded and enhanced the reaction, respectively. A mechanism involving the enol of benzoylacetaldehyde at a branching point of the pathway leading to 1,3,5-tribenzoylbenzene and acetophenone was suggested.

Get access to the full text of this article

Ancillary