中村 光 (ナカムラ アキラ)

  • 薬学部 創薬科学科 講師
Last Updated :2024/03/02

コミュニケーション情報 byコメンテータガイド

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    毒性の低い反応剤を利用した、環境にやさしい有機化学反応の開発研究をしています。また医薬品の原料となる物質の効率的な合成を行っています。

研究者情報

学位

  • 薬学博士(大阪大学大学院)

ホームページURL

科研費研究者番号

  • 50706629

J-Global ID

研究キーワード

  • 有機合成化学   合成化学   複素環合成   

現在の研究分野(キーワード)

    毒性の低い反応剤を利用した、環境にやさしい有機化学反応の開発研究をしています。また医薬品の原料となる物質の効率的な合成を行っています。

研究分野

  • ナノテク・材料 / 有機合成化学 / 触媒反応
  • ライフサイエンス / 薬系化学、創薬科学 / 有機合成化学

経歴

  • 2024年04月 - 現在  同志社大学生命医科学部 医情報学科准教授(有期)
  • 2019年04月 - 2024年03月  近畿大学薬学部講師
  • 2014年04月 - 2019年03月  近畿大学薬学部助教

所属学協会

  • 有機合成化学協会   日本薬学会   日本化学会   ヨウ素学会   日本プロセス化学会   

研究活動情報

論文

  • Junpei Matsuoka; Yuna Yano; Yuuka Hirose; Koushi Mashiba; Nanako Sawada; Akira Nakamura; Tomohiro Maegawa
    The Journal of Organic Chemistry 89 1 770 - 777 2023年12月
  • Akira Nakamura; Jyunya Morimoto; Maho Taniguchi; Haruka Aoyama; Jiadong He; Tomohiro Maegawa
    Tetrahedron Letters 126 154656 - 154656 2023年08月 [査読有り]
     
    A variety of aromatic and aliphatic hydroxamic acids were transformed into carboxylic acids employing tetra-n-butylammonium iodide and hydrogen peroxide. The reaction was executed across a range of substrates encompassing diverse functional groups, delivering good to excellent yields. This catalytic hydrolysis features gentle reaction conditions and the application of a non-hazardous, cleanly processed, and easy-to-manage oxidant.
  • Akira Nakamura; Tohko Kine; Haruna Uenishi; Yuri Maki; Yasuhito Kase; Mayo Takagi; Tomohiro Maegawa
    Synlett 34 11 1253 - 1258 2023年02月 [査読有り]
     
    Abstract We have developed a regioselective synthesis of 3,4-disubstituted isoxazoles by using a chalcone-rearrangement strategy. The reaction of β-ketoacetals with hydroxylamine hydrochloride and pyridine afforded the corresponding 3,4-disubstituted isoxazoles via isoxazolines or oximes. Depending on the substrate, another disubstituted isomer was also obtained under our optimized conditions, and a reaction mechanism for each transformation is proposed.
  • Akira Nakamura; Fei Rao; Kazuchika Ukiya; Riko Matsunaga; Shin-ichiro Ohira; Tomohiro Maegawa
    Organic & Biomolecular Chemistry 21 6 1134 - 1137 2022年12月 [査読有り]
     
    Herein we present a simple and efficient method for the synthesis of thioaurones (hemithioindigos) from MOM-protected 2′-mercaptochalcones with NBS and pyridine.
  • Akira Nakamura; Akira Imamiya; Yuichiro Ikegami; Fei Rao; Harumi Yuguchi; Yasuyoshi Miki; Tomohiro Maegawa
    RSC Advances 12 47 30426 - 30431 2022年10月 [査読有り]
     
    A method for the highly selective synthesis of two benzofuran isomers, 3-formylbenzofurans and 3-acylbenzofurans, by rearranging and subsequently transforming 2-hydroxychalcones has been developed.
  • Tomohiro Maegawa; Yasuyoshi Miki; Ryohei Oishi; Ayumi Maekawa; Kazutoshi Segi; Hiromi Hamamoto; Akira Nakamura
    Synthesis 54 18 4095 - 4103 2022年09月 [査読有り]
     
    Abstract We investigated the reaction of ketoximes with hypervalent iodine reagents. A combination of PhI(OAc)2 and BF3·Et2O promoted the Beckmann rearrangement of ketoximes, thus yielding the corresponding amides. From a detailed investigation of the reaction, we determined that the Beckmann rearrangement is preceded by acetylation of the hydroxy group of the ketoxime in situ, accelerating the Beckmann rearrangement. We confirmed that the acetylated ketoxime undergoes the Beckmann rearrangement with BF3·Et2O. The reaction of ketoximes with Koser’s reagent [PhI(OH)OTs] in the presence of tetrahydrofuran results in hydrolysis, affording the corresponding ketones in high yields at room temperature.
  • Tomohiro Maegawa; Akira Nakamura; Kouhei Yamamoto; Ryo Murakami; Norihito Kawashita; Kouichi Matsumoto
    Synthesis 53 20 3862 - 3868 2021年06月 [査読有り]
     
    Abstract A method for synthesizing six-membered heterocyclic compounds was developed based on the features of O,P-acetals. Sequential reactions of intramolecular cyclization between the methylene carbon atom of O,P-acetal and its electrophilic functional group (ester or protected carbamate) was followed by Horner–Wadsworth–Emmons (HWE) olefination with various aldehydes. The developed one-pot method yielded isochroman-4-one and benzoxazin-3-one derivatives with an alkylidene moiety.
  • Tomohiro Maegawa; Kana Yoshikawa; Takanori Tabata; Kazuma Fujimura; Natsumi Kuraoka; Akira Nakamura; Yasuyoshi Miki
    HETEROCYCLES 103 2 1031 - 1031 2021年 [査読有り]
  • 超原子価ヨウ素試薬を利用した アルドキシムの官能基選択的酸化反応の開発
    中村光; 加納穂嵩; 田中淳規; 三木康義; 前川智弘
    SIS Report(ヨウ素学会会報) 23 2020年11月
  • Akira Nakamura; Kazuki Mimaki; Ken-ichi Tanigami; Tomohiro Maegawa
    Frontiers in Chemistry 8 2020年03月 [査読有り][招待有り]
  • Aromatic Halogenation Using N‑Halosuccinimide and PhSSiMe3 or PhSSPh
    Yuuka Hirose; Mirai Yamazaki; Misa Nogata; Akira Nakamura; Tomohiro Maegawa
    J. Org. Chem. 84 7405 - 7410 2019年04月 [査読有り]
  • Ayako Shibata; Sara Kitamoto; Kazuma Fujimura; Yuuka Hirose; Hiromi Hamamoto; Akira Nakamura; Yasuyoshi Miki; Tomohiro Maegawa
    Synlett 29 2275 - 2278 2018年09月 [査読有り]
  • Ryohei Oishi; Kazutoshi Segi; Hiromi Hamamoto; Akira Nakamura; Tomohiro Maegawa; Yasuyoshi Miki
    Synlett 29 11 1465 - 1468 2018年07月 [査読有り]
     
    We developed a Beckmann rearrangement employing hypervalent iodine reagent under mild conditions. The reaction of ketoxime with hypervalent iodine afforded the corresponding ketone, but premixing of hypervalent iodine and a Lewis acid was effective for promoting Beckmann rearrangement. Aromatic and aliphatic ketoximes were converted into their corresponding amides in good to high yields.
  • Tomohiro Maegawa; Ryota Mizui; Miki Urasaki; Kazuma Fujimura; Akira Nakamura; Yasuyoshi Miki
    ACS Omega 3 5 5375 - 5381 2018年05月 [査読有り]
     
    A novel approach for synthesizing chalcones by Pd-catalyzed oxidative coupling is described. This is the first report of the efficient coupling reaction of acetanilides with phenyl vinyl ketones under mild conditions. Selective C-H activation occurred next to the acetamide group to afford 2-aminochalcone derivatives. The reaction proceeded under an O2 atmosphere without any chemical co-oxidants.
  • Construction of Azaisoflavone Derivatives by Hypervalent Iodine Reagent-Mediated Oxidative Rearrangement of 2’-Nitrochalcone
    Akira Nakamura; Junki Tanaka; Junya Morimoto; Tomohiro Maegawa
    Heterocycles 97 2018年05月 [査読有り]
  • Akira Nakamura; Hodaka Kanou; Junki Tanaka; Akira Imamiya; Tomohiro Maegawa; Yasuyoshi Miki
    Organic and Biomolecular Chemistry 16 4 541 - 544 2018年 [査読有り]
     
    A mild oxidation method for the conversion of aldoximes to carboxylic acids was developed mediated by hypervalent iodine reagents. This method covers a wide range of functionalized aldoximes and proceeds under mild conditions, utilizing PhI(OH)OTs as an oxidant.
  • Akira Nakamura; Satoshi Tanaka; Akira Imamiya; Reo Takane; Chiaki Ohta; Kazuma Fujimura; Tomohiro Maegawa; Yasuyoshi Miki
    ORGANIC & BIOMOLECULAR CHEMISTRY 15 32 6702 - 6705 2017年08月 [査読有り]
     
    An efficient one-pot method was developed for the construction of 3-acylindoles via oxidative rearrangement of 2-aminochalcones followed by intramolecular cyclization. The reaction was used to convert a variety of 2-aminochalcones into 3-acylindoles in moderate to high yields.
  • Tomohiro Maegawa; Misa Nogata; Yuuka Hirose; Shun Ohgami; Akira Nakamura; Yasuyoshi Miki; Hiromichi Fujioka
    Journal of Organic Chemistry 82 14 7608 - 7613 2017年07月 [査読有り]
     
    A novel transformation reaction of methylene acetals, using a combination of trimethyl(phenylthio)silane (PhSTMS) and N-bromosuccinimide (NBS) under mild reaction conditions, is described. Various methylene acetals were converted to their corresponding bromoformates in good to high yields. Under the given conditions, the reaction proceeded via a radical pathway. Further transformation of bromoformates to their corresponding epoxides was achieved by treatment with NaOMe.
  • Yasuyoshi Miki; Yukari Hirata; Noriko Makino; Yuuka Hirose; Misa Nogata; Akira Nakamura; Hiromi Hamamoto; Tomohiro Maegawa
    HETEROCYCLES 94 7 1269 - 1279 2017年07月 [査読有り]
     
    We studied selective bromination and iodination of dimethyl indole-2,3-dicarboxylates using phenyliodine diacetate (PIDA), LiBr, and LiI in the presence of Lewis acid. The protective group on the nitrogen of indole is important for selectivity of the halogenation position, and the use of a benzenesulfonyl group as a protective group resulted in preferential halogenation of indole at the 6-position.
  • Tomohiro Maegawa; Misa Nogata; Takaya Honda; Akira Nakamura; Yasuyoshi Miki
    HETEROCYCLES 95 1 608 - 614 2017年01月 [査読有り]
     
    A novel approach to producing the quinoline skeleton from 2-aminochalcone was developed. Treatment of benzyloxycarbonyl (Cbz)-protected 2-aminochalcones with BF3 center dot Et2O afforded quinoline derivatives via the deprotection of the Cbz group and isomerization of olefin in a one-pot reaction. The reaction of various 2-aminochalcones proceeded to give the corresponding 2-arylquinoline derivatives in good yields. This method is applicable to the rapid synthesis of dubamine.
  • Koji Morimoto; Akira Nakamura; Toshifumi Dohi; Yasuyuki Kita
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 25 25 4294 - 4297 2016年09月 [査読有り]
     
    The hypervalent-iodine-mediated oxidative metal-free cross-coupling reaction of thiophenes with various pyrroles was developed. The corresponding thiophene-pyrrole derivatives were obtained in moderate to high yields (up to 85 %). This method features high efficiency and regioselectivity and broad functional group tolerance. We further determined the highly planar characteristics of the 3,4-ethylenedioxythiophene-pyrrole biaryls caused by intramolecular hydrogen bonding.
  • Koji Morimoto; Yusuke Ohnishi; Daichi Koseki; Akira Nakamura; Toshifumi Dohi; Yasuyuki Kita
    ORGANIC & BIOMOLECULAR CHEMISTRY 14 38 8947 - 8951 2016年 [査読有り]
     
    Pyrrole-aryl derivatives are important due to their unique biological activities in medicinal chemistry. We now report a new oxidative biaryl coupling for pyrroles and indoles toward various arenes using a hypervalent iodine reagent and an appropriate stabilizer for pyrrolyl iodonium intermediates. The reactions readily provide a variety of desired coupling products in good yields.
  • Hiromi Hamamoto; Hideaki Umemoto; Misako Umemoto; Chiaki Ohta; Emi Fujita; Akira Nakamura; Tomohiro Maegawa; Yasuyoshi Miki
    HETEROCYCLES 91 3 561 - 572 2015年03月 [査読有り]
     
    Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-bromooxindole. However, the reaction of 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2,3-dibromo-1-(phenylsulfonyl)indole. In a similar manner, the 2,3-dichloro- and 2,3-diiodoindole derivatives could be obtained by the reaction of the indole-2,3-dicarboxylic acids with PIDA in the presence of lithium chloride and iodide. This method was optimized to the synthesis of polybromoindole alkaloids.
  • Hideaki Umemoto; Takuya Onaka; Yasuyoshi Miki; Akira Nakamura; Tomohiro Maegawa
    SYNLETT 26 2 205 - 208 2015年01月 [査読有り]
     
    The reaction of 2-[(trimethylsilyl) methyl]-2H-tetrazoles with various alkyl halides and carbonates using n-butyllithium or lithium diisopropylamide (LDA) gave 2-[1-(trimethylsilyl) alkyl]-2H-tetrazoles and (2H-tetrazol-2-yl) acetates as useful synthons of modified tetrazoles.
  • Kenichi Murai; Junki Nakajima; Akira Nakamura; Norimichi Hyogo; Hiromichi Fujioka
    CHEMISTRY-AN ASIAN JOURNAL 9 12 3511 - 3517 2014年12月 [査読有り]
     
    The results of studies leading to the development of enantioselective desymmetrizing, bromolactonization reactions of symmetric olefinic dicarboxylic acids, which are promoted by a C-3-symmetric trisimidazoline catalyst, are described. These processes generated carboxylic-acid-containing bromolactones in moderately high enantiomeric excesses. The results of optimization studies showed that reactions in a mixed solvent system of toluene and acetone proceeded with the highest levels of enantioselectivity. NMR studies probing the interactions between the catalyst and dicarboxylic acid substrates, as well as the effect of acetone on the stereochemistry of the process, are also described.
  • Hideaki Umemoto; Takuya Onaka; Yasuyoshi Miki; Akira Nakamura; Tomohiro Maegawa
    HETEROCYCLES 89 11 2545 - 2553 2014年11月 [査読有り]
     
    2-((Trimethylsilyl)methyl)-2H-tetrazoles were treated with aldehydes and ketones in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to give 2-(2-hydroxyethyl)-2H-tetrazoles. This simple procedure offers a valuable strategy for the preparation of 2-(hydroxyethyl)-2H-tetrazoles.
  • Takuya Onaka; Hideaki Umemoto; Yasuyoshi Miki; Akira Nakamura; Tomohiro Maegawa
    JOURNAL OF ORGANIC CHEMISTRY 79 14 6703 - 6707 2014年07月 [査読有り]
     
    A mild and regioselective 2-arylation of 5-substituted tetrazoles is described. The reaction proceeds regioselectively with a variety of arylboronic acids in the presence of [Cu(OH)(TMEDA)](2)Cl-2 to afford 2,5-disubstituted tetrazoles. This is the first report of highly regioselective arylation of 5-alkyltetrazoles.
  • Koji Morimoto; Yusuke Ohnishi; Akira Nakamura; Kazuma Sakamoto; Toshifumi Dohi; Yasuyuki Kita
    ASIAN JOURNAL OF ORGANIC CHEMISTRY 3 4 382 - 386 2014年04月 [査読有り]
     
    A method for coupling azoles with pyrroles and related compounds using a hypervalent iodine reagent has been developed. The oxidative coupling to produce the CN bond directly from CH and NH bonds is attractive in view of sustainable chemistry by avoiding prefunctionalization of the substrates. Notably, the reactions are found to be N-1-selective at the azoles and tolerant of a broad range of substrates and functional groups.
  • Kenichi Murai; Tomoyo Matsushita; Akira Nakamura; Norimichi Hyogo; Junki Nakajima; Hiromichi Fujioka
    Organic Letters 15 10 2526 - 2529 2013年05月 [査読有り]
     
    A strategically novel kinetic resolution of beta-substituted olefinic carboxylic acids is developed by asymmetric bromolactonization using an organocatalyst, 4-tBuPh-tris 1b. The cyclization stage, which provides delta-lactone, is proposed to be operative for discrimination of each enantiomer of carboxylic acids.
  • Kenichi Murai; Akira Nakamura; Tomoyo Matsushita; Masato Shimura; Hiromichi Fujioka
    CHEMISTRY-A EUROPEAN JOURNAL 18 27 8448 - 8453 2012年07月 [査読有り]
     
    A method for conducting enantioselective bromolactonization reactions of trisubstituted alkenoic acids, using the C3-symmetric trisimidazoline 1 and 1,3-dibromo-5,5-dimethyl hydantoin as a bromine source, has been developed. The process generates chiral d-lactones that contain a quaternary carbon. The results of studies probing geometrically different olefins show that (Z)-olefins rather than (E)-olefins are favorable substrates for the process. The method is not only applicable to acyclic olefin reactants but can also be employed to transform cyclic trisubstituted olefins into chiral spirocyclic lactones. Finally, the synthetic utility of the newly developed process is demonstrated by its application to a concise synthesis of tanikolide, an antifungal marine natural product.
  • Kenichi Murai; Shunsuke Fukushima; Akira Nakamura; Masato Shimura; Hiromichi Fujioka
    Tetrahedron 67 26 4862 - 4868 2011年07月 [査読有り]
     
    We describe the necessity of the C-3-symmetry and the role of a third imidazoline of trisimidazoline 3, which was recently developed by us as a new entry of organocatalyst. The utility of 3 as a Bronsted base catalyst in the nitro Michael reaction and the alpha-amination of beta-ketoesters was shown, and the re-cyclability of the catalyst was also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.
  • Kenichi Murai; Tomoyo Matsushita; Akira Nakamura; Shunsuke Fukushima; Masato Shimura; Hiromichi Fujioka
    Angewandte Chemie 122 48 9360 - 9363 2010年10月 [査読有り]
  • Kenichi Murai; Tomoyo Matsushita; Akira Nakamura; Shunsuke Fukushima; Masato Shimura; Hiromichi Fujioka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 49 48 9174 - 9177 2010年 [査読有り]

共同研究・競争的資金等の研究課題

担当経験のある科目

  • 卒業研究近畿大学
  • 基礎ゼミ近畿大学
  • 総合薬学研究2近畿大学
  • 総合薬学研究1近畿大学
  • 創薬科学演習近畿大学
  • 創薬科学実習2近畿大学
  • 有機化学生薬学実習近畿大学
  • 基礎薬科学実習近畿大学
  • 基礎化学英語近畿大学
  • 化学英語近畿大学
  • 有機反応化学近畿大学
  • 合成化学近畿大学
  • 新創薬科学研究コース1近畿大学
  • 新創薬科学研究コース2近畿大学
  • オープンラボ2近畿大学
  • オープンラボ1近畿大学
  • 薬学英語近畿大学
  • 総合薬学研究3近畿大学
  • グローバル創薬演習近畿大学
  • メディシナルケミストリー近畿大学

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