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Environmentally Friendly Syntheses of Imines Applying the Pressure Reduction Technique: Reaction Cases of Less Reactive Amines and Studies by Computational Chemistry

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Green and Sustainable Chemistry 2020年第1期10卷 1-17页

作者： Shoko Suzuki Hiroyuki Ito Motoyoshi Noike shinji ishizuka Risehiro Nonaka Kenji Funaki Takeshi Kodama Shujiro Sakaki Tomomichi Nishino Mina Ito Toranosuke Takahasi Yasuo Yokoyama Faculty of Education Kyoto University of Education Kyoto Japan Department of Chemical and Biological Engineering National Institute of Technology Akita College Akita Japan Institute of Natural Medicine University of Toyama Toyama Japan Department of Applied Chemistry National Institute of Technology Akita College Akita Japan

Recently, the development of environmentally friendly syntheses of imine derivatives, which were attracting great attention for their reactivity and structure in various fields, progressed rapidly because the concept of green chemistry had deeply penetrated into society. In our previous work, we had reported new synthetic methods of imine derivatives using some active amines under solvent- and catalyst-free reaction conditions. This synthetic reaction proceeded smoothly and target compounds were obtained in excellent yields. In this system, when less reactive amines were used as substrates, the synthetic reaction was not finished in the short reaction time, and the corresponding compounds were given in moderate yields. In order to solve this point, we tried to improve the reaction conditions of this method. Through this improvement, it was found that pure target compounds could be obtained in excellent yields by using 1.1 equivalents of less reactive amines to aldehydes and extending the reaction time compared with our previous work. In this paper, we will introduce the detail of this study, and also report the result of the investigation of the reaction property by computational chemistry.

关键词： Solvent-Free Catalyst-Free Pressure Reduction Technique Imine Computational Chemistry

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Perfect Solvent- and Catalyst-Free Syntheses of Imine Derivatives Using the Pressure Reduction Technique

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Green and Sustainable Chemistry 2019年第4期9卷 105-118页

作者： Shoko Suzuki Hiroyuki Ito shinji ishizuka Risehiro Nonaka Motoyoshi Noike Takeshi Kodama Kenji Funaki Mizuho Taguchi Taisei Kagaya Sayaka Sato Guillaume Redler Yasuo Yokoyama Faculty of Education Kyoto University of Education Kyoto Japan Department of Chemical and Biological Engineering National Institute of Technology Akita College Akita Japan Environment Systems Engineering Course National Institute of Technology Akita College Akita Japan Department of Applied Chemistry National Institute of Technology Akita College Akita Japan Science et Génie des Matériaux IUT Blois Blois France.

In the field of organic syntheses, the development of environmentally friendly methods based on the concept of green chemistry has been always required. In response to this requirement, we reported solvent- and catalyst-free syntheses of imines using the pressure reduction technique as a key technology. We found that this reaction proceeded very rapidly in the initial stage, but its rate decreased with the passage of time. It was also found that the reaction of benzaldehyde with aniline had a specificity that the phase transition occurred. In this method, the desired imines could be obtained in good to excellent yields, but target compounds had to be given by purifications using organic solvents. Therefore, we tried to develop the perfect synthetic method of imine derivatives without organic or inorganic solvents. We selected two methods and took them into this investigation. One was exactly mixing (1:1, substance ratio) aldehydes and amines and the other was employing lower pressure (>0.1 mmHg, previous method: 1.0 mmHg) at the pressure reducing technique. When this improved synthetic method was performed, it was revealed that pure target imines were obtained in excellent yields without any purification.

关键词： Solvent-Free Catalyst-Free Neat Reaction Pressure Reduction Technique Imine

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Efficient Solvent- and Catalyst-Free Syntheses of Imine Derivatives Applying the Pressure Reduction Technique: Remarkable Change of the Reaction Rate with the Phase Transition

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Green and Sustainable Chemistry 2018年第2期8卷 167-179页

作者： Shoko Suzuki Shujiro Sakaki shinji ishizuka Tomomichi Nishino Hiroyuki Ito Risehiro Nonaka Motoyoshi Noike Takeshi Kodama Hajime Nozaka Tsuneyuki Sato Hitoshi Agematsu Koichi Maruyama Shun Oyamada Takashi Kuroishi Kazuma Sasaki Kei Yagawa Mami Yoshioka Yasuo Yokoyama Faculty of Education Kyoto University of Education Kyoto Japan Department of Chemical and Biological Engineering National Institute of Technology Akita College Akita Japan Environment Systems Engineering Course National Institute of Technology Akita College Akita Japan Department of Applied Chemistry National Institute of Technology Akita College Akita Japan

Because imines could be used as convenient starting materials in various fields, the development of an easy synthetic method of imine was strongly desired. In response to this demand, we thought that it would be an effective synthesis method if an aldehyde and an amine could be reacted to give an imine in good yield under solvent- and catalyst-free conditions. In fact, we tried the reaction of benzaldehyde with various amines under solvent- and catalyst-free conditions followed by removal of water that was produced in the reaction system by a vacuum pump, and desired imines could be obtained in good yields. Observation of this reaction using a nuclear magnetic resonance spectrometer revealed that the reaction rate was extremely fast at the initial stage but slowed over time. However, the reaction of benzaldehyde with aniline differed greatly, and the reaction rate dramatically improved in 47 - 48 minutes after the start of the reaction. At this time, we found that the reaction system underwent a phase transition from the liquid phase to the solid phase.

关键词： Solvent-Free Catalyst-Free Pressure Reduction Technique Imine Reaction Rate Phase Transition

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Perfect Solvent- and Catalyst-Free Syntheses of Imine Derivatives Using the Pressure Reduction Technique

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Green and Sustainable Chemistry（绿色与可持续化学） 2019年第4期

作者： Shoko Suzuki Hiroyuki Ito shinji ishizuka Risehiro Nonaka Motoyoshi Noike Takeshi Kodama Kenji Funaki Mizuho Taguchi Taisei Kagaya Sayaka Sato Guillaume Redler Yasuo Yokoyama

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