 | NAKAMURA AkiraDepartment of Pharmaceutical Sciences Lecturer | ||
Last Updated :2023/12/05
Researcher Information
Research funding number
- 50706629
J-Global ID
Research Interests
- 有機合成化学 合成化学 複素環合成
Research Areas
- Nanotechnology/Materials / Synthetic organic chemistry
- Life sciences / Pharmaceuticals - chemistry and drug development
Association Memberships
Published Papers
- Akira Nakamura; Jyunya Morimoto; Maho Taniguchi; Haruka Aoyama; Jiadong He; Tomohiro MaegawaTetrahedron Letters Elsevier BV 126 154656 - 154656 0040-4039 2023/08 [Refereed]
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 MaegawaSynlett Georg Thieme Verlag KG 34 (11) 1253 - 1258 0936-5214 2023/02 [Refereed]
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 NakamuraYAKUGAKU ZASSHI Pharmaceutical Society of Japan 143 (2) 105 - 110 0031-6903 2023/02 [Refereed][Invited]
- A concise synthesis of thioaurones via NBS-induced cyclization of MOM-protected 2′-mercaptochalconesAkira Nakamura; Fei Rao; Kazuchika Ukiya; Riko Matsunaga; Shin-ichiro Ohira; Tomohiro MaegawaOrganic & Biomolecular Chemistry Royal Society of Chemistry (RSC) 21 (6) 1134 - 1137 1477-0520 2022/12 [Refereed]
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 MaegawaRSC Advances Royal Society of Chemistry (RSC) 12 (47) 30426 - 30431 2022/10 [Refereed]
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 NakamuraSynthesis Georg Thieme Verlag KG 54 (18) 4095 - 4103 0039-7881 2022/09 [Refereed]
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 MatsumotoSynthesis Georg Thieme Verlag KG 53 (20) 3862 - 3868 0039-7881 2021/06 [Refereed]
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 MikiHETEROCYCLES The Japan Institute of Heterocyclic Chemistry 103 (2) 1031 - 1031 0385-5414 2021 [Refereed]
- 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) 2020/11
- Akira Nakamura; Kazuki Mimaki; Ken-ichi Tanigami; Tomohiro MaegawaFrontiers in Chemistry Frontiers Media SA 8 2020/03 [Refereed][Invited]
- Aromatic Halogenation Using N‑Halosuccinimide and PhSSiMe3 or PhSSPhYuuka Hirose; Mirai Yamazaki; Misa Nogata; Akira Nakamura; Tomohiro MaegawaJ. Org. Chem. 84 7405 - 7410 2019/04 [Refereed]
- Ayako Shibata; Sara Kitamoto; Kazuma Fujimura; Yuuka Hirose; Hiromi Hamamoto; Akira Nakamura; Yasuyoshi Miki; Tomohiro MaegawaSynlett 29 2275 - 2278 2018/09 [Refereed]
- Ryohei Oishi; Kazutoshi Segi; Hiromi Hamamoto; Akira Nakamura; Tomohiro Maegawa; Yasuyoshi MikiSynlett Georg Thieme Verlag 29 (11) 1465 - 1468 1437-2096 2018/07 [Refereed]
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 MikiACS Omega American Chemical Society 3 (5) 5375 - 5381 2470-1343 2018/05 [Refereed]
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’-NitrochalconeAkira Nakamura; Junki Tanaka; Junya Morimoto; Tomohiro MaegawaHeterocycles 97 2018/05 [Refereed]
- Akira Nakamura; Hodaka Kanou; Junki Tanaka; Akira Imamiya; Tomohiro Maegawa; Yasuyoshi MikiOrganic and Biomolecular Chemistry Royal Society of Chemistry 16 (4) 541 - 544 1477-0520 2018 [Refereed]
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 MikiORGANIC & BIOMOLECULAR CHEMISTRY ROYAL SOC CHEMISTRY 15 (32) 6702 - 6705 1477-0520 2017/08 [Refereed]
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 FujiokaJournal of Organic Chemistry American Chemical Society 82 (14) 7608 - 7613 1520-6904 2017/07 [Refereed]
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 MaegawaHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 94 (7) 1269 - 1279 0385-5414 2017/07 [Refereed]
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 MikiHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 95 (1) 608 - 614 0385-5414 2017/01 [Refereed]
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 KitaEUROPEAN JOURNAL OF ORGANIC CHEMISTRY WILEY-V C H VERLAG GMBH 25 (25) 4294 - 4297 1434-193X 2016/09 [Refereed]
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 KitaORGANIC & BIOMOLECULAR CHEMISTRY ROYAL SOC CHEMISTRY 14 (38) 8947 - 8951 1477-0520 2016 [Refereed]
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 MikiHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 91 (3) 561 - 572 0385-5414 2015/03 [Refereed]
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 MaegawaSYNLETT GEORG THIEME VERLAG KG 26 (2) 205 - 208 0936-5214 2015/01 [Refereed]
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 FujiokaCHEMISTRY-AN ASIAN JOURNAL WILEY-V C H VERLAG GMBH 9 (12) 3511 - 3517 1861-4728 2014/12 [Refereed]
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 MaegawaHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 89 (11) 2545 - 2553 0385-5414 2014/11 [Refereed]
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 MaegawaJOURNAL OF ORGANIC CHEMISTRY AMER CHEMICAL SOC 79 (14) 6703 - 6707 0022-3263 2014/07 [Refereed]
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 KitaASIAN JOURNAL OF ORGANIC CHEMISTRY WILEY-V C H VERLAG GMBH 3 (4) 382 - 386 2193-5807 2014/04 [Refereed]
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 FujiokaORGANIC LETTERS AMER CHEMICAL SOC 15 (10) 2526 - 2529 1523-7060 2013/05 [Refereed]
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 FujiokaCHEMISTRY-A EUROPEAN JOURNAL WILEY-V C H VERLAG GMBH 18 (27) 8448 - 8453 0947-6539 2012/07 [Refereed]
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 FujiokaTETRAHEDRON PERGAMON-ELSEVIER SCIENCE LTD 67 (26) 4862 - 4868 0040-4020 2011/07 [Refereed]
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 FujiokaAngewandte Chemie 122 (48) 9360 - 9363 2010/10 [Refereed]
- Kenichi Murai; Tomoyo Matsushita; Akira Nakamura; Shunsuke Fukushima; Masato Shimura; Hiromichi FujiokaANGEWANDTE CHEMIE-INTERNATIONAL EDITION WILEY-V C H VERLAG GMBH 49 (48) 9174 - 9177 1433-7851 2010 [Refereed]