研究者詳細 - 菅　誠治

論文 - 菅　誠治

分割表示 154 件中 61 - 80 件目／全件表示 >>

Facile Synthesis of 1,4-Bis(diaryl)-1,3-butadiynes Bearing Two Amino Moieties by Electrochemical Reaction-Site Switching, and Their Solvatochromic Fluorescence

Natsuyo Kamimoto, Nariaki Nakamura, Akina Tsutsumi, Hiroki Mandai, Koichi Mitsudo, Atsushi Wakamiya, Yasujiro Murata, Jun-ya Hasegawa, Seiji Suga

ASIAN JOURNAL OF ORGANIC CHEMISTRY 5 ( 3 ) 373 - 379 2016年3月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

Bis(diaryl)-1,3-butadiynes bearing two amino moieties were easily synthesized by a sequential coupling reaction by using an electrochemical method. This sequential reaction consists of electrochemical oxidative homocoupling and Suzuki-Miyaura coupling. The fluorescence of the obtained bis(diaryl)-1,3-butadiynes is solvatochromic despite their symmetric linear structure and lack of a strong acceptor moiety.

DOI： 10.1002/ajoc.201500502

Bacteriogenic iron oxide as an effective catalyst for Baeyer-Villiger oxidation with molecular oxygen and benzaldehyde

Kyoko Mandai, Minae Hanata, Koichi Mitsudo, Hiroki Mandai, Seiji Suga, Hideki Hashimoto, Jun Takada

TETRAHEDRON 71 ( 50 ) 9403 - 9407 2015年12月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

Iron oxide produced by iron-oxidizing bacteria, Leptothrix ochracea, (L-BIOX) obtained from a freshwater purification plant, Joyo City in Kyoto, Japan catalyzed Baeyer-Villiger oxidation with molecular oxygen in the presence of benzaldehyde at 25 degrees C more efficiently than usual iron compounds. L-BIOX can promote the reactions of various substrates to give the desired products in sufficient yields and was found to be reusable. Scanning transmission electron microscopy and Fe-57 Mossbauer spectroscopy revealed that no change of the surface structure of L-BIOX was observed even after four times of the recycling test and the oxidation state of iron in L-BIOX is trivalent before and after the oxidation of cyclohexanone. An investigation with analogous amorphous iron oxides which contain silicon revealed that the catalytic activity of L-BIOX might stem from a synergetic effect of iron and silicon in the structure. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2015.10.057

Synthesis and Properties of Ethene-Bridged Terthiophenes

Koichi Mitsudo, Hidehiko Sato, Arata Yamasaki, Natsuyo Kamimoto, Jun Goto, Hirold Mandai, Seiji Suga

ORGANIC LETTERS 17 ( 19 ) 4858 - 4861 2015年10月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

A method for the facile synthesis of ethene-bridged terthiophenes (EBTTs) in two steps has been developed. The first step is a double Sonogashira coupling between 3',4'-dibromo-2,2':5',2 ''-terthiophene and terminal alkynes to give dialkynylated terthiophenes, and the second step is a cyclization reaction to afford EBTTs. The fundamental physical properties of EBTTs were also studied.

DOI： 10.1021/acs.orglett.5b02417

Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives

Hiroki Mandai, Takuma Fujiwara, Katsuaki Noda, Kazuki Fujii, Koichi Mitsudo, Toshinobu Korenaga, Seiji Suga

ORGANIC LETTERS 17 ( 18 ) 4436 - 4439 2015年9月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

Chiral N,N-4-(dimethylamino)pyridine (DMAP) derivatives, which can be readily prepared by the Ugi multicomponent reaction in a one-pot manner, have been efficiently applied to the enantioselective Steglich rearrangement of oxindole derivatives to give the desired products bearing a quaternary carbon center in high yield (>98% yield) and with high enantioselectivity (up to 99:1 er).

DOI： 10.1021/acs.orglett.5b02089

Palladium-Catalyzed Domino CH/NH Functionalization: An Efficient Approach to Nitrogen-Bridged Heteroacenes

Natsuyo Kamimoto, Dieter Schollmeyer, Koichi Mitsudo, Seiji Suga, Siegfried R. Waldvogel

CHEMISTRY-A EUROPEAN JOURNAL 21 ( 22 ) 8257 - 8261 2015年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

Palladium-catalyzed domino CH/NH functionalization for the synthesis of novel nitrogen-bridged thienoacenes and 10H-benzo[4,5]thieno[3,2-b]indole derivatives from dihaloarene is reported. This domino sequence consists of initial CH functionalization of the benzo[b]thiophene moiety, followed by Buchwald-Hartwig coupling. This transformation is also useful for the synthesis of highly -extended compounds.

DOI： 10.1002/chem.201500897

Development of Cross-Coupling Reactions Including Electro-oxidative Processes and Their Applications to the Synthesis of pi-Extended Compounds

Koichi Mitsudo, Hideo Tanaka, Seiji Suga

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 73 ( 2 ) 171 - 180 2015年2月

記述言語：日本語出版者・発行元：SOC SYNTHETIC ORGANIC CHEM JPN

An electrochemical method to synthesize cationic palladium complexes has been developed. Their counter anions could be changed readily by the electrolyte. The reaction could be incorporated into electro-oxidative palladium catalyzed reactions, such as Wacker-type reaction, homo-coupling of arylboronic acids, oxidative Sonogashira-type coupling, and Glaser-type coupling of terminal alkynes. These reactions exhibited a wide scope and a variety of products were obtained in high yields due to high activity of electrogenerated palladium species. We also developed site-selective sequential reactions by the integration of the electro-oxidative coupling reactions with non-electrochemical reactions. The reaction site could be controlled completely by the on/off application of electricity.

DOI： 10.5059/yukigoseikyokaishi.73.171

Organoelemental compounds

Jun-Ichi Yoshida, Toshiki Nokami, Seiji Suga

Organic Electrochemistry, Fifth Edition: Revised and Expanded 1357 - 1392 2015年1月

記述言語：英語掲載種別：論文集(書籍)内論文出版者・発行元：CRC Press

The organoelemental compounds such as group 1, 2, 13, and 14 organoelemental compounds have played a major role in organic synthesis and enjoy widespread use in both laboratories and industry. Some organoelemental compounds such as organosilicon compounds are also utilized as materials. Some organoelemental compounds, such as group 1 and 2 organoelemental compounds, are also called organometallic compounds. However, in this chapter, we call them organoelemental compounds. The electrochemistry of other organometallic compounds, especially transition metal compounds, is discussed in Chapter 36. This chapter will focus on the electrochemical synthesis and reactions of organic compounds containing main group elements. The electrochemistry of organoelemental compounds has a long history, and enormous advances have been made in the study of this field so far. The scope of this subject is, therefore, too extensive to be covered completely in a single chapter. There are excellent review articles on general electrochemistry of organoelemental compounds [1-9] and specific topics [10-12] in this field. Thus, the approach here is to present those fundamental aspects of electrochemical synthesis and reactions of organoelemental compounds with special emphasis on recent developments. This chapter is not an exhaustive compilation of all known reactions, but rather sampling of sufficient variety to illustrate the fascinating chemistry of electrochemical synthesis and reactions of organoelemental compounds.

Low temperature in situ Raman spectroscopy of an electro-generated arylbis(arylthio)sulfonium ion

Kouichi Matsumoto, Yu Miyamoto, Kazuaki Shimada, Yusuke Morisawa, Hendrik Zipse, Seiji Suga, Jun-ichi Yoshida, Shigenori Kashimura, Tomonari Wakabayashi

CHEMICAL COMMUNICATIONS 51 ( 66 ) 13106 - 13109 2015年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ROYAL SOC CHEMISTRY

A low temperature in situ Raman spectroscopic method was developed for the detection of unstable intermediates in electro-organic chemistry. It was effective for monitoring the generation of ArS(ArSSAr)(+) by the electrochemical oxidation of ArSSAr (Ar = p-FC6H4) in Bu4NBF4/CH2Cl2 at 195 K. The intensity of a Raman band at 427 cm(-1), which is attributable to the S-S vibration of ArS(ArSSAr)(+), increased with an increase in the electricity until 2/3 F of the electricity was consumed, whereas decreased with a further increase in the electricity indicating the decomposition of ArS(ArSSAr)(+).

DOI： 10.1039/c5cc03585f

4．電解発生カチオン性パラジウム触媒を用いる有機合成

光藤耕一, 菅誠治

Electrochemistry 83 ( 6 ) 477 - 482 2015年

Preparation and Capacitive Performance of Mesoporous Carbon with Short Time CO2 Activation

Akinori Muto, Keiichiro Itano, Shohei Wada, Shunsuke Ohtani, Hayato Tokumoto, Seiji Suga

ELECTROCHEMISTRY 82 ( 12 ) 1067 - 1071 2014年12月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ELECTROCHEMICAL SOC JAPAN

The porous carbon material was prepared from sawdust impregnated with a 0.1 M FeCl3 aqueous solution with CO2 activation at 800 degrees C. Pores were found to develop with increasing activation time. The BET surface area, average pore diameter and volume of the mesopores also became greater with increasing activation time. The ratio of the mesopore to total pore volume in the activated carbon was more than 90% after 5 min of activation. Precise control of the pore size distribution is possible by finely tuning the activation time. The porous carbonized material was examined for use in electric double layer capacitor (EDLC) electrodes. The charge and discharge characteristics of EDLC electrodes using these carbonized materials were studied. Cyclic voltammetry and rate performance indicated good correlation between the pore structure of the carbonaceous materials and the magnitude of the electrolyte. These relationships were in good agreement with the Nyquist plot obtained by measuring the impedance. These results were also in accordance with pore structure analysis obtained using the nitrogen adsorption method. It is suggested that the Nyquist diagram characterizes the pore structure of porous carbon from the viewpoint of ion transfer. (C) The Electrochemical Society of Japan, All rights reserved.

DOI： 10.5796/electrochemistry.82.1067

Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts

Hiroki Mandai, Kazuhiro Omori, Daisuke Yamamoto, Toki Tsumura, Kyouta Murota, Satoshi Yamamoto, Koichi Mitsudo, Soichiro Ibaragi, Akira Sasaki, Hiroshi Maeda, Shogo Takashiba, Seiji Suga

BIOORGANIC & MEDICINAL CHEMISTRY 22 ( 19 ) 5338 - 5344 2014年10月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

Interleukin (IL)-6 is a proinflammatory cytokine that performs a wide variety of biological functions, including important roles in the progression of chronic inflammatory diseases such as periodontal disease. (+)-Terrein, a secondary bioactive fungal metabolite isolated from Aspergillus terreus, has various biological activities; however, its anti-inflammatory effects are still unknown. The purpose of this study was to examine the effect of synthetic (+)-terrein on IL-6 signaling and related protein production in human gingival fibroblasts. To our knowledge, this study is the first to report that synthetic (+)-terrein is not cytotoxic at concentrations less than 20 mu M and suppresses IL-6/soluble IL-6 receptor (sIL-6R)-induced phosphorylation of signal transducer and activator of transcription-3, extracellular signal-regulated kinase 1/2, and c-jun N-terminal kinase 1/2-signaling proteins that are downstream of IL-6 signaling. In addition, synthetic (+)-terrein suppresses IL-6/sIL-6R-induced vascular endothelial growth factor (VEGF) secretion in a concentration-dependent manner (p < 0.01). These data suggest that synthetic (+)-terrein has potential anti-IL-6 signaling activity and suppresses VEGF-associated inflammatory disease progression. (C) 2014 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2014.07.047

An Efficient Petasis Boronic-Mannich Reaction of Chiral Lactol Derivatives Prepared from D-Araboascorbic Acid

Hiroki Mandai, Hiroshi Yamada, Keita Shimowaki, Koichi Mitsudo, Seiji Suga

SYNTHESIS-STUTTGART 46 ( 19 ) 2672 - 2681 2014年10月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：GEORG THIEME VERLAG KG

Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis boronic-Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from D-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.

DOI： 10.1055/s-0034-1378900

Remarkable Enhancement of the Rate of the Intramolecular MoritaBaylis- Hillman Reaction by the Combination of a Nucleophilic Catalyst and 1,3-Diphenyl-2-thiourea

Hiroki Mandai, Keita Shimowaki, Koichi Mitsudo, Seiji Suga

ASIAN JOURNAL OF ORGANIC CHEMISTRY 3 ( 4 ) 437 - 441 2014年4月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

The rate of the intramolecular Morita-Baylis-Hillman (MBH) reaction is remarkably enhanced by the combination of catalytic amounts of a nucleophilic catalyst (4-dimethylaminopyridine (DMAP), 4-pyrrolidinopyridine (PPY), or PBu3) and 1,3-diphenyl-2-thiourea, and the desired MBH adducts are obtained in good to high yields within a few hours.

DOI： 10.1002/ajoc.201402001

Addition of N-Acyliminium Ion Pools to Alkenes Having a Nucleophilic Moiety: Integration of Intermolecular and Intramolecular Reactions

Yosuke Ashikari, Yohei Kiuchi, Tomoya Takeuchi, Koji Ueoka, Seiji Suga, Jun-ichi Yoshida

CHEMISTRY LETTERS 43 ( 2 ) 210 - 212 2014年2月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：CHEMICAL SOC JAPAN

The reaction of electrochemically generated N-acyliminium ion pools with alkenes bearing a heteroatom nucleophilic functionality such as a hydroxy group, a carboxy group, and an oxime moiety led to intermolecular carbon carbon bond formation followed by intramolecular carbon heteroatom bond formation to give the corresponding heterocyclic compounds such as cyclic ethers, lactones, and 2-isoxazolines, respectively.

DOI： 10.1246/cl.130947

Electrogenerated Acid (EGA)-catalyzed Addition of Diaryl Disulfides to Carbon-Carbon Multiple Bonds

Kouichi Matsumoto, Hayato Shimazaki, Tomonari Sanada, Kazuaki Shimada, Shino Hagiwara, Seiji Suga, Shigenori Kashimura, Jun-ichi Yoshida

CHEMISTRY LETTERS 42 ( 8 ) 843 - 845 2013年8月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：CHEMICAL SOC JAPAN

Addition of diaryl disulfides to carbon-carbon multiple bonds was achieved with a catalytic amount of an electrogenerated acid (EGA), which was produced by the electrolysis of Bu4N+B(C6F5)(4)(-)/CH2Cl2. The anti-addition products of two ArS groups across the carbon-carbon multiple bond were obtained in good yields.

DOI： 10.1246/cl.130255

Recyclable Palladium Catalyst in PEG/CH3CN Biphasic System for Electro-oxidative Wacker-type Reaction

Koichi Mitsudo, Satoshi Fukunaga, Tomoya Fujita, Hiroki Mandai, Seiji Suga, Hideo Tanaka

ELECTROCHEMISTRY 81 ( 5 ) 347 - 349 2013年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ELECTROCHEMICAL SOC JAPAN

Electro-oxidative Wacker-type reaction has been developed in PEG/CH3CN thermomorphic biphasic system. The heterogeneous solution was turned into homogeneous solution with heating to 60 degrees C, and electro-oxidative Wacker-type reactions of alkenes bearing long alkyl chains proceeded smoothly to afford methyl ketones in good yields. The recycling of PEG phase containing Pd has also been achieved. (C) The Electrochemical Society of Japan, All rights reserved.

DOI： 10.5796/electrochemistry.81.347

Electro-reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile

Koichi Mitsudo, Takahiro Okada, Shuichi Shimohara, Hiroki Mandai, Seiji Suga

ELECTROCHEMISTRY 81 ( 5 ) 362 - 364 2013年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ELECTROCHEMICAL SOC JAPAN

An electro-reductive halogen-deuterium exchange reaction in CD3CN has been developed. Using 9-fluorenone as a mediator, the electro-reduction of several aryl halides proceeded smoothly to give the deuterated products selectively. A methylation reaction of aryl halides also proceeded under similar conditions. (C) The Electrochemical Society of Japan, All rights reserved.

DOI： 10.5796/electrochemistry.81.362

The Addition of ArSSAr to Alkenes: The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)(+)

Kouichi Matsumoto, Tomonari Sanada, Hayato Shimazaki, Kazuaki Shimada, Shino Hagiwara, Shunsuke Fujie, Yosuke Ashikari, Seiji Suga, Shigenori Kashimura, Jun-ichi Yoshida

ASIAN JOURNAL OF ORGANIC CHEMISTRY 2 ( 4 ) 325 - 329 2013年4月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WILEY-V C H VERLAG GMBH

The addition reactions of diaryl disulfides (ArSSAr) to alkenes and alkynes were achieved with a catalytic amount of an arylbis(arylthio)sulfonium ion (ArS(ArSSAr)(+)), which was generated and accumulated by low-temperature electrolysis of ArSSAr, to give the corresponding diarylthiolated products. The electrolysis of a mixture of ArSSAr and an alkene with a catalytic amount of electricity was also effective to drive the reactions. A cation chain mechanism mediated by ArS(ArSSAr)(+) as a chain carrier is suggested.

DOI： 10.1002/ajoc.201300017

Synthesis of Hexa(furan-2-yl)benzenes and Their pi-Extended Derivatives

Koichi Mitsudo, Jyunji Harada, Yo Tanaka, Hiroki Mandai, Chie Nishioka, Hideo Tanaka, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

JOURNAL OF ORGANIC CHEMISTRY 78 ( 6 ) 2763 - 2768 2013年3月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER CHEMICAL SOC

The first synthesis of hexa(furan-2-yl)benzene derivatives is described. The RhCl3/i-Pr2NEt-catalyzed cyclotrimerization of di(furan-2-yl)acetylenes was an effective method for constructing hexa(furan-2-yl)benzene derivatives in good yields. Their pi-extended derivatives were also synthesized by Suzuki-Miyaura coupling between hexakis(5-Bpinfuran-2-yl)benzene (Bpin = (pinacolato)boryl) and several aryl iodides.

DOI： 10.1021/jo302652r

KINETIC RESOLUTION OF SECONDARY ALCOHOLS BY CHIRAL DMAP DERIVATIVES PREPARED BY THE UGI MULTICOMPONENT REACTION

Hiroki Mandai, Shunsuke Irie, Masaru Akehi, Kazunobu Yuri, Masaaki Yoden, Koichi Mitsudo, Seiji Suga

HETEROCYCLES 87 ( 2 ) 329 - 340 2013年2月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

The kinetic resolution of secondary alcohols was examined by new chiral DMAP derivatives, which can readily be prepared by the Ugi multicomponent reaction in a one-pot operation. The initial screening of DMAP derivatives indicated that the catalyst bearing L-valine with an S configuration at the a-position of amide showed the best stereoselectivity factor. After the reaction conditions were optimized with (S,S)-4a in the kinetic resolution of secondary alcohols, various acyclic and cyclic secondary alcohols could be resolved with an s-factor of up to 12.

DOI： 10.3987/COM-12-12624

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