Updated on 2024/12/19

写真a

 
NISHIOKA Hiromi
 
Organization
Faculty of Medicine, Dentistry and Pharmaceutical Sciences Assistant
Position
Assistant
External link

Degree

  • 薬学博士 ( 岡山大学 )

Research Interests

  • 有機化学

  • Synthetic Chemistry

  • Organic Chemistry

  • 合成化学

Research Areas

  • Life Science / Pharmaceutical chemistry and drug development sciences

Education

  • Okayama University   薬学部   製薬化学科

    - 1992

    　 More details

    Country： Japan

    researchmap

  • Okayama University    

    - 1992

    　 More details

Research History

  • Okayama University   学術研究院医歯薬学域   Research Assistant

    2022.4

    　 More details

  • Okayama University   学術研究院医歯薬学域   Assistant Professor

    2021.4 - 2022.3

    　 More details

  • Okayama University   医歯薬学総合研究科   Assistant Professor

    2004.4 - 2021.3

    　 More details

  • - Assistant Professor,Graduate School of Medicine, Dentistry and Pharmaceutical Sciences,Okayama University

    2004

    　 More details

Professional Memberships

 

Papers

  • Competitive binding assay with an umbelliferone-based fluorescent rexinoid for retinoid X receptor ligand screening Reviewed

    Shoya Yamada, Mayu Kawasaki, Michiko Fujihara, Masaki Watanabe, Yuta Takamura, Maho Takioku, Hiromi Nishioka, Yasuo Takeuchi, Makoto Makishima, Tomoharu Motoyama, Sohei Ito, Hiroaki Tokiwa, Shogo Nakano, Hiroki Kakuta

    Journal of Medicinal Chemistry   62 ( 19 )   8809 - 8818   2019.9

    　More details

    Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1021/acs.jmedchem.9b00995

    researchmap

  • Correction to Synthesis of 11C-Labeled RXR Partial Agonist 1-[(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzotriazole-5-carboxylic Acid (CBt-PMN) by Direct [11C]Carbon Dioxide Fixation via Organolithiation of Tri Reviewed

    Shibahara O, Watanabe M, Takamura Y, Yamada S, Akehi M, Sasaki T, Akahoshi A, Hanada T, Hirano H, Nakatani S, Nishioka H, Takeuchi Y, Kakuta H

    Journal of medicinal chemistry   62 ( 9 )   4780 - 4781   2019.5

    　More details

    Language：English   Publisher：AMER CHEMICAL SOC  

    DOI： 10.1021/acs.jmedchem.9b00617

    Web of Science

    PubMed

    researchmap

  • Structure-activity relationship of indoloquinoline analogs anti-MRSA Reviewed

    Zhao M, Kamada T, Takeuchi A, Nishioka H, Kuroda T, Takeuchi Y

    Bioorg. Med. Chem. Lett.   25   5551 - 5554   2015.6

    　More details

    Language：English   Publishing type：Research paper (scientific journal)  

    researchmap

  • Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source Reviewed

    Hideyuki Suzuki, Seiki Yoshioka, Ami Igesaka, Hiromi Nishioka, Yasuo Takeuchi

    TETRAHEDRON   69 ( 31 )   6399 - 6403   2013.8

    　More details

    Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    We designed ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] for use as a solvent and hydrogen donor for hydrogenation. Catalytic hydrogenation of aromatic ketones, nitro groups, and olefins with PdCl2 in [BHEA][HCO2] generated the corresponding reduction products. Selective reduction of aromatic ketones over aliphatic ketones was observed. Hydrogenolysis of benzyl ethers and benzyl amines also proceeded. All these reactions were successfully carried out in good to excellent yields under mild and nonflammable conditions. In addition, the ionic liquid and Pd source can be reused several times. (C) 2013 Elsevier Ltd. All rights reserved.

    DOI： 10.1016/j.tet.2013.05.103

    Web of Science

    researchmap

  • Non-flammable and reusable hydrogenation of aromatic ketones in ionic liquid Reviewed

    Hideyuki Suzuki, Hiromi Nishioka, Yasuo Takeuchi

    TETRAHEDRON LETTERS   53 ( 28 )   3686 - 3688   2012.7

    　More details

    Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    A novel method of hydrogenation of aromatic ketones in the ionic liquid [BHEA][HCO2] was developed; this method is more enhanced in terms of flammability and reusability as compared to the conventional method (H-2 and Pd/C). The reductive selectivities of aromatic and aliphatic ketones in this method were observed. (C) 2012 Elsevier Ltd. All rights reserved.

    DOI： 10.1016/j.tetlet.2012.05.066

    Web of Science

    researchmap

MISC

  • Controlled hydrogenation of diphenylacetylene using alkylammonium formate

    Hideyuki Suzuki, Ikkyu Satoh, Hiromi Nishioka, Yasuo Takeuchi

    TETRAHEDRON LETTERS   58 ( 40 )   3834 - 3837   2017.10

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    A simple and straightforward semihydrogenation of alkyne to alkene with triethanolamine and formic acid in the presence of PdCl2 has been described. Although hydrogenation using formic acid as a hydrogenation source has been used in combination with amines previously, few reports are available concerning the associated reactivity. We demonstrated that reactivity changes depending on the type of amine used in the hydrogenation. Further, this reaction requires no strict time control, making it a useful tool in organic synthesis. (C) 2017 Elsevier Ltd. All rights reserved.

    DOI： 10.1016/j.tetlet.2017.08.054

    Web of Science

    researchmap

  • Synthesis of C-11-Labeled RXR Partial Agonist 14(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)aminoThenzotriazole-5-carboxylic Acid (CBt-PMN) by Direct [C-11]Carbon Dioxide Fixation via Organolithiation of Trialkyltin Precursor and PET Imaging Thereof

    Osamu Shibahara, Masaki Watanabe, Shoya Yamada, Masaru Akehi, Takanori Sasaki, Akiya Akahoshi, Takahisa Hanada, Hiroyuki Hirano, Shunsuke Nakatani, Hiromi Nishioka, Yasuo Takeuchi, Hiroki Kakuta

    JOURNAL OF MEDICINAL CHEMISTRY   60 ( 16 )   7139 - 7145   2017.8

    　More details

    Language：English   Publisher：AMER CHEMICAL SOC  

    The retinoid X receptor (RXR) partial agonist 1-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzotriazole-5-carboxylic acid (1; CBt-PMN, E-max = 75%, EC50 = 143 nM) is a candidate for treatment of central nervous system (CNS) diseases such as Alzheimers and Parkinsons diseases based on reports that RXR-full agonist 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene) shows therapeutic effects on these disease in rodent models. Here, we synthesized carbon-11-labeled ([C-11]1) as a tracer for positron emission tomography (PET) and used it in a PET imaging study to examine the brain uptake and biodistribution of 1. We found that (CO2)-C-11 fixation after tinlithium exchange at -20 degrees C afforded [C-11]1. This methodology may also be useful for synthesizing (CO2H)-C-11-PET tracer derivatives of other compounds bearing pi-rich heterocyclic rings. A PET/CT imaging study of [C-11]1 in mice indicated 1 is distributed to the brain and is thus a candidate for treatment of CNS diseases.

    DOI： 10.1021/acs.jmedchem.7b00817

    Web of Science

    researchmap

  • Synthesis and Anti-human Immunodeficiency Virus Activity of the Skeleton Isomers of 3 ',4 '-Di-(O)-(-)-camphanoyl-(+)-khellactone

    Hiromi Nishioka, Koji Uesugi, Norihiro Ueda, Yuka Kondo, Megumi Tsuji, Hitoshi Abe, Takashi Harayama, Takayuki Hamasaki, Masanori Baba, Yasuo Takeuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN   59 ( 8 )   1075 - 1076   2011.8

    　More details

    Language：English   Publisher：PHARMACEUTICAL SOC JAPAN  

    Optically active structural isomers (1b-f and dst-1b-f) of 3',4'-di-(O)-(-)-camphanoyl-(+)-khellactone (DCK) were synthesized and their anti-human immunodeficiency virus (HIV) activity was investigated. The value of the sensitivity index (SI) of 1b was greater than that of DCK.

    DOI： 10.1248/cpb.59.1075

    Web of Science

    researchmap

  • Synthesis of (-)-Actinonin

    Shin-ichi Inoue, Hiromi Nishioka, Hitoshi Abe, Takashi Harayama, Yasuo Takeuchi

    SYNTHESIS-STUTTGART   2011 ( 11 )   1705 - 1710   2011.6

    　More details

    Language：English   Publisher：GEORG THIEME VERLAG KG  

    Synthesis of (-)-actinonin in 17% overall yield was accomplished in seven steps via the formation of an isoimide derivative as the key intermediate. The synthesis was carried out using commercially available dimethyl maleate without the use of a highly expensive reagent.

    DOI： 10.1055/s-0030-1260461

    Web of Science

    researchmap

  • Synthesis of acinetobactin

    Yasuo Takeuchi, Satoru Ozaki, Masahiro Satoh, Ken-Ichiro Mimura, Sei-Ichi Hara, Hitoshi Abe, Hiromi Nishioka, Takashi Harayama

    Chemical and Pharmaceutical Bulletin   58 ( 11 )   1552 - 1553   2010.11

    　More details

    Language：English  

    A structure involving the absolute configuration of acinetobactin (1b) was clarified. It was reconfirmed that preacinetobactin (1a) produced 1b by a rearrangement reaction. © 2010 Pharmaceutical Society of Japan.

    DOI： 10.1248/cpb.58.1552

    Scopus

    PubMed

    researchmap

  • Concise Asymmetric Synthesis of (+)-Febrifugine Utilizing trans-Selective Intramolecular Conjugate Addition

    Satoshi Sukemoto, Miyo Shige, Masahiro Sato, Ken-ichiro Mimura, Hiromi Nishioka, Hitoshi Abe, Takashi Harayama, Yasuo Takeuchi

    SYNTHESIS-STUTTGART   2008 ( 19 )   3081 - 3087   2008.10

    　More details

    Language：English   Publisher：GEORG THIEME VERLAG KG  

    Intramolecular conjugate addition of gamma-substituted (E)-alpha,beta-unsaturated ketones with a Lewis acid (BF(3)center dot OEt(2)) Selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction.

    DOI： 10.1055/s-2008-1067271

    Web of Science

    researchmap

  • Studies toward the synthesis of toddaquinoline by intramolecular cyclization

    Georgeta Serban, Yasurni Shigeta, Hiromi Nishioka, Hitoshi Abe, Yasuo Takeuchi, Takashi Harayama

    HETEROCYCLES   71 ( 7 )   1623 - 1630   2007.7

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    In connection with studies on the total synthesis of toddaquinoline (1), the synthesis of [1,3]dioxolo[4',5':4,5]benzo[h]quinoline (1a), which is the tetracyclic core of 1, was investigated. Intramolecular benzene -pyridine coupling reactions of the monobromide (9) and dibromide (10), using a Pd reagent and Cu reagent, were evaluated to produce I a in poor to moderate yields.

    Web of Science

    researchmap

  • Biaryl coupling reactions of 3-methoxy-N-(2-iodophenyl)-N-methylbenzamide and 3-methoxycarbonyl-N-(2-iodophenyl)-N-methylbenzamide using palladium reagent

    Hiromi Nishioka, Chie Nagura, Hitoshi Abe, Yasuo Takeuchi, Takashi Harayama

    HETEROCYCLES   70   549 - +   2006.12

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    We examined palladium-assisted biaryl coupling reactions of 3-methoxy and 3-methoxycarbonyl benzanilidcs, and propose an aspect of the mechanism involved in forming a biaryl bond using Pd reagent.

    DOI： 10.3987/COM-06-S(W)10

    Web of Science

    researchmap

  • Novel synthesis of benzoxazoles from O-nitrophenols and amines

    H Nishioka, Y Ohmori, Y Iba, E Tsuda, T Harayama

    HETEROCYCLES   64   193 - 198   2004.12

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    o-Nitrophenols and o-nitroanilme were reacted with amines at 210-215degreesC to produce the corresponding benzoxazoles and benzimidazoles, respectively, in moderate yields. The reactions between o-nitrophenols containing a CO2Me or OMe group on their benzene rings and N,N-diethylanitine were examined to investigate the effects of the position and electronic character of these substituents on the formation of the oxazole ring.

    DOI： 10.3987/COM-04-S(P)11

    Web of Science

    researchmap

  • Intramolecular Pd-catalyzed biaryl coupling reaction of N-aryl-2-triflyloxybenzamides using Pd(OAc)(2) 1,3-bis[diphenylphosphino]propane, Bu3P, and DBU

    H Nishioka, Y Shoujiguchi, H Abe, Y Takeuchi, T Harayama

    HETEROCYCLES   64   463 - 466   2004.12

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    Intramolecular Pd-catalyzed coupling reactions of N-aryl-2-triflyloxybenzamides were examined. The procedure using DBU as a base was effective for even in the reaction of oxygen-substituted benzamides.

    DOI： 10.3987/COM-04-S(P)7

    Web of Science

    researchmap

  • Synthetic studies on pyrrolophenanthridone skeleton from 1-benzoyl-7-iododihydroindole derivatives using palladium-assisted biaryl coupling reactions

    T Harayama, H Toko, A Hori, T Miyagoe, T Sato, H Nishioka, H Abe, Y Takeuchi

    HETEROCYCLES   61   513 - +   2003.12

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    The biaryl coupling reaction of 1-benzoyl-7-iododihydroindole derivatives using Pd reagent was examined. 1-[(1,3-Benzodioxol-5-yl)carbonyl]-7-iodo-2,3-dihydroindole gave 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one, which was formed by connection to a more hindered carbon, as a major product. 1-(3,4-Dimethoxybenzoyl)-7-iodo-2,3-dihydroindole gave oxoassoanine and 10,11-dimethoxy-4,5-dihydropyrrolo[3,2,1-de]phenanthridin-7-one in an almost equal ratio.

    Web of Science

    researchmap

  • Concise synthesis of tetrahydrophenanthridone by palladium reagent

    T Harayama, H Toko, H Nishioka, H Abe, Y Takeuchi

    HETEROCYCLES   59 ( 2 )   541 - 546   2003.3

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    Heck reaction of N-(2-halophenyl)-N-methyl-1-cyclohexene-1-carboxamide (1) and 2-bromo-N-methyl-N-phenyl-1-cyclohexene-1-carboxamide (4) using a palladium reagent under several reaction conditions was examined. Reaction of 4 using Pd(OAc)(2), DPPP, and Bu3P afforded tetrahydrophenanthridone (5) in excellent yield.

    Web of Science

    researchmap

  • Synthesis of febrifugine derivatives and a solution to the puzzle of the structural determination of febrifugine

    Y Takeuchi, K Azuma, M Oshige, H Abe, H Nishioka, K Sasaki, T Harayama

    TETRAHEDRON   59 ( 10 )   1639 - 1646   2003.3

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    The stereo-structure of piperidine lactone (3), a synthetic intermediate of the antimalarial agent febrifugine ((+)-1) with a piperidine ring in the trans relative configuration, was re-revised to the cis-form. We determined that isomerization to the trans-form from the cis-form occurred in the stage (6 from 5) of deprotection in Baker's synthesis. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI： 10.1016/S0040-4020(03)00139-X

    Web of Science

    researchmap

  • Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. IV: Improved synthetic method of substituted coumarins

    Y Takeuchi, N Ueda, K Uesugi, H Abe, H Nishioka, T Harayama

    HETEROCYCLES   59 ( 1 )   217 - 224   2003.1

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    The reaction of salicylaldehydes (2) with Horner-Wadsworth-Emmons (HWE) or Ando-HWE reagents was attempted to afford intramolecular phosphonate derivatives (6). A new synthetic method for coumarins (1) was achieved by using protected 2.

    Web of Science

    researchmap

  • Concise Synthesis of 11H-Indolizino[1,2-b]quinolin-9-one by an Aryl-Aryl Coupling Reaction Using Pd Reagent

    Takashi Harayama, Yoshiaki Morikami, Akihiro Hori, Hiromi Nishioka, Hitoshi Abe, Yasuo Takeuchi

    Heterocycles   2003

    　More details

  • Studies on the selective intramolecular biaryl coupling reaction of 2-triflyloxy-6-halobenzanilides using a palladium reagent

    T Harayama, H Toko, K Kubota, H Nishioka, H Abe, Y Takeuchi

    HETEROCYCLES   58   175 - 181   2002.11

    　More details

    Language：English   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

    The aryl-aryl coupling reaction of 2-triflyloxy-6-halobenzanilides using a palladium reagent under several reaction conditions was examined. The 6-iodo compound gave triflyloxyphenanthridone selectively in excellent yield under the conditions for the ordinary Heck reaction.

    Web of Science

    researchmap

  • Aryl-aryl coupling reaction using a novel and highly active palladium reagent prepared from Pd(OAc)(2), 1,3-bis [diphenylphosphino]propane (DPPP), and Bu3P

    T Harayama, T Akiyama, Y Nakano, H Nishioka, H Abe, Y Takeuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN   50 ( 4 )   519 - 522   2002.4

    　More details

    Language：English   Publisher：PHARMACEUTICAL SOC JAPAN  

    A palladium-assisted coupling reaction of aryl triflate with arene was investigated, and a novel Pd reagent prepared from equimolar Pd(OAc)(2), 1,3-Bis[diphenylphosphino]propane (DPPP), and BUY was developed. This method is useful for intramolecular biaryl coupling reactions, not only between aryl triflate and arene (triflate-amide), but also between aryl halide and arene (halo-amide).

    DOI： 10.1248/cpb.50.519

    Web of Science

    researchmap

  • Synthesis and antimalarial activity of febrifugine derivatives

    Y Takeuchi, M Koike, K Azuma, H Nishioka, H Abe, HS Kim, Y Wataya, T Harayama

    CHEMICAL & PHARMACEUTICAL BULLETIN   49 ( 6 )   721 - 725   2001.6

    　More details

    Language：English   Publisher：PHARMACEUTICAL SOC JAPAN  

    The regioisomers (2a,b) of the piperidine ring of febrifugine (1a) and isofebrifugine (1b) were synthesized from 4-allyl-3-piperidone (5). Reduction of 5 afforded a mixture of the trans and cis alcohols (6a,b) without diastereoselectivity: this result differentiated it from the reduction of 2-allyl-3-piperidone (14), The antimalarial activity of 2a,b and related compounds was tested.

    DOI： 10.1248/cpb.49.721

    Web of Science

    researchmap

  • Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

    Y Takeuchi, Y Nagao, K Toma, Y Yoshikawa, T Akiyama, H Nishioka, H Abe, T Harayama, S Yamamoto

    CHEMICAL & PHARMACEUTICAL BULLETIN   47 ( 9 )   1284 - 1287   1999.9

    　More details

    Language：English   Publisher：PHARMACEUTICAL SOC JAPAN  

    Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

    DOI： 10.1248/cpb.47.1284

    Web of Science

    researchmap

  • Baeyer-Villiger reaction of benzaldehydes possessing oxygen functions with SeO2-H2O2

    H Nishioka, K Katsuno, M Fujii, Y Nishita, N Koshiba, T Narayama

    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN   119 ( 7 )   519 - 528   1999.7

    　More details

    Language：Japanese   Publisher：PHARMACEUTICAL SOC JAPAN  

    The Baeyer-Villiger (B.V.) reaction using SeO2-H2O2 was examined for various benzaldehydes possessing methoxy groups and/or a furan ring. When benzaldehydes have an electron-donating group (methoxy group) at the ortho or para position to a formyl group, the B.V. reaction proceeded rapidly and in a good yield. Since the reaction using SeO2-H2O2 is carried out under a neutral condition, this reaction are applicable to aldehyde derivatives with a furan ring which is unstable against acid.

    DOI： 10.1248/yakushi1947.119.7_519

    Web of Science

    researchmap

  • SYNTHETIC STUDIES ON BROMOCOUMARINS POSSESSING OXYGEN FUNCTION

    H NISHIOKA, N HAYASHIDA, S KAWABE, T HARAYAMA

    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN   115 ( 9 )   765 - 772   1995.9

    　More details

    Language：Japanese   Publisher：PHARMACEUTICAL SOC JAPAN  

    The reaction of bromo-methoxysalicylaldehyde (4-6) and broma-hydroxysalicylaldehyde (18) with carbethoxymethylenetriphenylphosphorane (2) in diethylaniline under reflux gave unexpected debromocoumarins along with an expected bromocoumarin. The oxygen function might facilitate debromination in the process of coumarin synthesis at an elevated temperature.

    DOI： 10.1248/yakushi1947.115.9_765

    Web of Science

    researchmap

  • CONVENIENT SYNTHESIS OF A SIMPLE COUMARIN FROM SALICYLALDEHYDE AND WITTIG REAGENT .3. SYNTHESIS OF NITROCOUMARINS

    T HARAYAMA, K NAKATSUKA, H NISHIOKA, K MURAKAMI, Y OHMORI, Y TAKEUCHI, H ISHII, K KENMOTSU

    HETEROCYCLES   38 ( 12 )   2729 - 2738   1994.12

    　More details

    Language：English   Publisher：ELSEVIER SCIENCE BV  

    Reaction of nitrosalicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in Et(2)NPh, in Ph(2)O, and in the absence of solvent (neat) at 210-215 degrees C was investigated. Reaction of 3-nitrosalicylaldehyde (1d) in Et(2)NPh afforded the benzoxazole (6) and the aminocoumarin (3e) along with the expected coumarin (3d). It was clarified that the origin of carbon-unit introduced for the formation of the benzoxazole ring came from the alkyl group of solvent.

    Web of Science

    researchmap

  • CONVENIENT SYNTHESIS OF A SIMPLE COUMARIN FROM SALICYLALDEHYDE AND WITTIG REAGENT .2. SYNTHESIS OF BROMOCOUMARIN AND METHOXYCARBONYLCOUMARIN

    T HARAYAMA, K NAKATSUKA, H NISHIOKA, K MURAKAMI, N HAYASHIDA, H ISHII

    CHEMICAL & PHARMACEUTICAL BULLETIN   42 ( 10 )   2170 - 2173   1994.10

    　More details

    Language：English   Publishing type：Article, review, commentary, editorial, etc. (scientific journal)   Publisher：PHARMACEUTICAL SOC JAPAN  

    Reaction of salicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in diethylaniline under reflux gave coumarins (3) in moderate to high yield except 3-methoxycarbonylsalicylaldehyde (1e) as summarized in Table I. The substituent effects are discussed. A substituent at C-6 on 1 usually facilitated the formation of the coumarin ring regardless of its electronic character.

    DOI： 10.1248/cpb.42.2170

    Web of Science

    researchmap

  • ALKOXYCARBONYLMETHYLATION OF (3R,10BS)-3-PHENYL-2,3,5,6-TETRAHYDRO-10BH-OXAZOLO[2,3-A]ISOQUINOLINE

    Y TAKEUCHI, Y KAMADA, K NISHIMURA, H NISHIOKA, M NISHIKAWA, K HASHIGAKI, M YAMATO, T HARAYAMA

    CHEMICAL & PHARMACEUTICAL BULLETIN   42 ( 4 )   796 - 801   1994.4

    　More details

    Language：English   Publisher：PHARMACEUTICAL SOC JAPAN  

    As part of a series of studies on synthesis of chiral 1-alkyltetrahydroisoquinolines, asymmetric synthesis of 1-alkoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline (IV) was investigated. Two synthetic approaches using intermolecular and intramolecular Reformatsky-type reactions from (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline (1) were attempted, but high stereoselectivity could not be obtained. For the purpose of determining the absolute structures of the compounds (2, 3) obtained by the Reformatsky-type reactions, transformation of 3a to a chiral 1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine (14) was investigated.

    DOI： 10.1248/cpb.42.796

    Web of Science

    researchmap

  • A CONVENIENT PREPARATION OF SALICYLALDEHYDES FROM 2-METHYLBENZOFURANS BY OZONOLYSIS

    H ISHII, S OHTA, H NISHIOKA, N HAYASHIDA, T HARAYAMA

    CHEMICAL & PHARMACEUTICAL BULLETIN   41 ( 6 )   1166 - 1168   1993.6

    　More details

    Language：English   Publishing type：Article, review, commentary, editorial, etc. (scientific journal)   Publisher：PHARMACEUTICAL SOC JAPAN  

    A convenient and effective transformation of 2-methylbenzofuran (B) to salicylaldehyde (C) was achieved by ozonolysis of B in CH2Cl2 at -78-degrees-C followed by alkaline hydrolysis.

    DOI： 10.1248/cpb.41.1166

    Web of Science

    researchmap

  • On the Products of Reaction of Ortho-Nitrophenols with Amines.

    Chemistry Express   8 ( 9 )   769   1993

    　More details

  • A Convenient Synthesis of Coumarin Using the Wittig Reagent.

    Chemistry Express   8 ( 4 )   245   1993

    　More details

  • On the Products of Reaction of Ortho-Nitrophenols with Amines.

    Chemistry Express   8 ( 9 )   769   1993

    　More details

  • A Convenient Synthesis of Coumarin Using the Wittig Reagent.

    Chemistry Express   8 ( 4 )   245   1993

    　More details

▼display all

Presentations

  • Pd反応系を用いたビアリール閉環反応における有機塩基の影響

    日本薬学会第124年会  2004 

    　More details

  • Wittig 試薬を用いた Coumarin 環形成反応における酸素官能基の影響

    第３９回日本薬学会・日本病院薬剤師会中国四国支部学術大会  2000 

    　More details

 

Class subject in charge

  • Experimental Organic Chemistry （2024academic year） 1st and 2nd semester  - その他5～9

  • Experimental Organic Chemistry （2024academic year） 1st and 2nd semester  - その他5～9

  • Clinical preparation education C （2024academic year） special  - その他

  • Basic Practice in Pharmaceutical Sciences （2024academic year） 1st semester  - その他5～9

  • Basic Practice in Pharmaceutical Sciences （2024academic year） 1st semester  - その他5～9

  • Basic Practice in Pharmaceutical Sciences （2024academic year） 1st semester  - その他5～9

  • Basic Practice in Pharmaceutical Sciences （2024academic year） 1st semester  - その他5～9

  • Practice in Fundamental Pharmaceutical Sciences II （2024academic year） 1st and 2nd semester  - その他5～9

  • Practice in Fundamental Pharmaceutical Sciences II （2024academic year） 1st and 2nd semester  - その他5～9

  • Experimental Organic Chemistry （2023academic year） 1st and 2nd semester  - その他5～9

  • Experimental Organic Chemistry （2023academic year） 1st and 2nd semester  - その他5～9

  • Basic Practice in Pharmaceutical Sciences （2023academic year） 1st semester  - その他5～9

  • Basic Practice in Pharmaceutical Sciences （2023academic year） 1st semester  - その他5～9

  • Basic Practice in Pharmaceutical Sciences （2023academic year） 1st semester  - その他5～9

  • Basic Practice in Pharmaceutical Sciences （2023academic year） 1st semester  - その他5～9

  • Practice in Fundamental Pharmaceutical Sciences II （2023academic year） 1st and 2nd semester  - その他5～9

  • Practice in Fundamental Pharmaceutical Sciences II （2023academic year） 1st and 2nd semester  - その他5～9

  • Development of Synthetic Drug I （2022academic year） special  - その他

  • Development of Synthetic Drug II （2022academic year） special  - その他

  • 薬学基本実習 （2022academic year） 第１学期  - その他5～9

  • 薬学基本実習 （2022academic year） 第１学期  - その他5～9

  • 薬学基礎実習II （2022academic year） １・２学期  - その他5～9

  • 薬学基礎実習II （2022academic year） １・２学期  - その他5～9

  • Seminar in Molecular Structure Analysis （2021academic year） Fourth semester  - 火3～4

  • Seminar in Molecular Structure Analysis （2021academic year） Fourth semester  - 火3～4

  • Synthetic & Medicinal Chemistry （2021academic year） special  - その他

  • Seminar on Synthetic & Medicinal Chemistry （2021academic year） special  - その他

  • Development of Synthetic Drug I （2021academic year） special  - その他

  • Development of Synthetic Drug II （2021academic year） special  - その他

  • Ethics for Pharmacist （2021academic year） Second semester  - その他

  • Ethics for Pharmacist （2021academic year） Second semester  - 火3～4

  • Basic Practice in Pharmaceutical Sciences （2021academic year） 1-3 semesters  - その他6～9

  • Basic Practice in Pharmaceutical Sciences （2021academic year） 1-3 semesters  - その他6～9

  • Practice in Fundamental Pharmaceutical Sciences II （2021academic year） 1st and 2nd semester  - その他6～9

  • Practice in Fundamental Pharmaceutical Sciences II （2021academic year） 1st and 2nd semester  - その他6～9

  • Seminar in Molecular Structure Analysis （2020academic year） Fourth semester  - その他

  • Seminar in Molecular Structure Analysis （2020academic year） Fourth semester  - その他

  • Chemistry a La Carte （2020academic year） 1st semester  - 月1,月2

  • Structural Analysis of Medicine （2020academic year） 1st-4th semester  - [第１学期]月1,月2, [第２学期]その他, [第３学期]その他, [第４学期]火3,火4

  • Synthetic & Medicinal Chemistry （2020academic year） special  - その他

  • Seminar on Synthetic & Medicinal Chemistry （2020academic year） special  - その他

  • Development of Synthetic Drug I （2020academic year） special  - その他

  • Development of Synthetic Drug II （2020academic year） special  - その他

  • Ethics for Pharmacist （2020academic year） Second semester  - 火3,火4

  • Basic Practice in Pharmaceutical Sciences （2020academic year） special  - その他

  • Basic Practice in Pharmaceutical Sciences （2020academic year） special  - その他

  • Practice in Fundamental Pharmaceutical Sciences II （2020academic year） special  - その他

  • Practice in Fundamental Pharmaceutical Sciences II （2020academic year） special  - その他

▼display all