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 |
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Authors: | Tanaka Makoto Nakamura Kazuya Iwado Tatsuya Sato Toshiyuki Okada Masaki Sue Kiwamu Iwamura Hiizu Hiaki Toshihiko |
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Affiliation: | College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino, Chiba 275-8575, Japan. |
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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. |
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Keywords: | cycloaddition high‐pressure chemistry Michael addition supercritical fluids water chemistry |
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