- Novel and efficient Lewis acids as catalysts for single-step synthesis of pyrano- and furoquinolines
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Some Lewis acids such as ZrCl4, SnCl4, TiCl 4, and PtCl4 have been found to be novel and highly efficient catalysts for one-pot coupling of the three components, anilines, aldehydes, and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran to produce the corresponding pyrano- or furoqinolines in high yields and high diastereoselectivity.
- Das, Biswanath,Ravinder Reddy,Saidi Reddy,Ramu
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- Phosphomolybdic acid-catalyzed efficient one-pot three-component aza-Diels-Alder reactions under solvent-free conditions: a facile synthesis of trans-fused pyrano- and furanotetrahydroquinolines
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trans-Fused pyrano- and furanotetrahydroquinoline derivatives have been synthesized via a one-pot three-component aza-Diels-Alder reaction of aryl imines formed in situ from aromatic amines and arylaldehydes with cyclic enol ethers,such as 3,4-dihydro-2H-
- Nagaiah,Sreenu,Rao, R. Srinivasa,Vashishta,Yadav
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- Simple and practical synthesis of pyrano- and furano[3,2-c]-quinoline derivatives under non-Lewis acid catalysis
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One-pot synthesis of substituted pyrano- and furano[3,2-c]quinoline derivatives from appropriately substituted anilines, substituted benzaldehydes and dienophiles via Povarov reaction catalyzed by HCl-ethanol were reported. Good to excellent yields with h
- Liu, Rui Huan,Yu, Xin,Hu, Liang,Yu, Nie Fang
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- Imino Diels-Alder reactions: One-pot synthesis of tetrahydroquinolines
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An efficient synthesis of tetrahydroquinoline derivatives is reported via three component coupling reactions of aldehydes and anilines with various dienophiles in the presence of a catalytic amount of perchloric acid adsorbed on silica gel (HClO4/su
- Kamble, Vinod T.,Davane, Bhaskar S.,Chavan, Sanjay A.,Muley, Dnyanoba B.,Atkore, Sandeep T.
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- An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines
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An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through Lewis acid activated Povarov reaction is described. The protocol takes advantage of the very cheap, easy to handle, and environmentally
- Cimarelli, Cristina,Bordi, Samuele,Piermattei, Pamela,Pellei, Maura,Del Bello, Fabio,Marcantoni, Enrico
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- An efficient one-pot synthesis of pyrano- and furoquinolines employing two reusable solid acids as heterogeneous catalysts
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Two solid acids, Fe3+-K-10 montmorillonite clay and HY-zeolite have been employed efficiently for single-step synthesis of pyrano- or furoquinolines in high yields and high diastereoselectivities by coupling of three components: anilines, benzaldehydes and 3,4-dihydro-2h-pyran or 2,3-dihydrofuran. Both the heterogeneous catalysts are recoverable and recyclable.
- Srinivas,Das, Biswanath
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- SnCl2·2H2O - An alternative to Lewis acidic ionic liquids
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Inexpensive and commercially available SnCl2·2H 2O has been shown to be an alternative to Lewis acidic ionic liquids by carrying out a variety of organic synthesis. The reaction medium is recycleable and the reaction time is comparable with the microwave reactions. Copyright
- Arumugam, Pandurangan,Perumal, Paramasivan T.
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- Aza-Diels-Alder reactions in ionic liquids: A facile synthesis of pyrano- and furanoquinolines
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Room temperature ionic liquids are found to catalyze efficiently the three component-coupling reactions of aldehydes, amines and cyclic enol ethers such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under mild and convenient conditions to afford the corres
- Yadav,Reddy,Reddy,Rao, R. Srinivasa
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- LiBF4-Catalyzed Imino-Diels-Alder Reaction: A Facile Synthesis of Pyrano- and Furoquinolines
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Lithium tetrafluoroborate efficiently catalyzes the imino-Diels-Alder reaction of aldimines with 3,4-dihydro-2H-pyran (DHP) and 2,3-dihydrofuran to afford the corresponding pyrano- and furoquinolines in high yields with high diastereoselectivity.
- Yadav, Jhillu S.,Reddy, Basi V. Subba,Madhuri, Chinti Rheddy,Sabitha, Gowravaram
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- Imino Diels-Alder reactions: Efficient synthesis of pyrano and furoquinolines catalyzed by ZrCl4
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Anhydrous zirconium tetrachloride is found to be an efficient catalyst for the Imino Diels-Alder reactions of N-benzylideneanilines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran to afford pyrano and furo [3,2-c] quinolines in good yields.
- Mahesh,Venkateshwar Reddy,Srinivasa Reddy,Raju,Narayana Reddy
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- Lanthanide complexes of the monovacant Dawson polyoxotungstate [α1-P2W17O61]10- as selective and recoverable Lewis acid catalysts
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(Chemical Equation Presented) Catalytic cornerstone: Lanthanide(III) complexes of a lacunary Dawson-type polyoxometalate catalyze Lewis acid mediated reactions (see figure, TMS = trimethylsilyl). The compounds (NBu 4)5H2[α
- Boglio, Cecile,Lemiere, Gilles,Hasenknopf, Bernold,Thorimbert, Serge,Lacote, Emmanuel,Malacria, Max
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- Natural product inspired diversity oriented synthesis of tetrahydroquinoline scaffolds as antitubercular agent
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An efficient natural product inspired diversity oriented syn thesis of tetrahydroquinoline analogues has been developed using the natural carbohydrate derived solid acid catalyst via multicomponent aza-Diels-Alder reaction of imine (generated in situ from
- Kumar, Atul,Srivastava, Suman,Gupta, Garima,Chaturvedi, Vinita,Sinha, Sudhir,Srivastava
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- Imidazolinium salts as catalysts for the aza-Diels-Alder reaction
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Various easily accessible imidazolinium salts have been found to be capable of catalysing an aza-Diels-Alder reaction with a range of imines and Danishefsky's diene, giving the desired products in good to excellent yields. The influence of the counter-anions on the reactivity has been explored. These salts could contribute to the field of metal-free catalysis/organocatalysis.
- Jurcik, Vaclav,Wilhelm, Rene
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- A facile and convenient three-component coupling protocol for the synthesis of pyrano and furoquinolines
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Ceric ammonium nitrate (CAN) catalyzes efficiently the coupling of anilines, benzaldehydes and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran to form the corresponding pyrano or furoquinolines in short reaction times and in high yields.
- Ravindranath,Ramesh,Reddy, M. Ravinder,Das, Biswanath
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- Copper (II) bromide-catalyzed imino Diels-Alder reaction: Synthesis of pyrano[3,2-c]- and furo [3,2-c]tetrahydroquinolines
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Copper(II) bromide is found to be an effective catalyst for the imino Diels-Alder reaction between an imine (generated in situ) and an activated alkene in acetonitrile at the ambient temperature. The reaction proceeds smoothly to afford the corresponding adduct as a mixture of chromatographically separable cis- and trans-isomers in moderate to good yields. Copyright Taylor & Francis LLC.
- Semwal, Abha,Nayak, Sandip K.
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- Radical cation salts induced aza-diels-alder reaction: Synthesis of hexahydrofuro[3,2-c]-quinoline derivatives
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Aza-Diels-Alder reaction between imines and 2,3-dihydrofuran under radical cation induced conditions was achieved and series of hexahydrofuro[3,2-c] quinoline derivatives was prepared. The stereoselectivity was affected by the substituents on imines, whic
- Jia, Zhong,Ren, Yan,Huo, Cong-De,Chen, Xiang-Ning,Tong, Chong-Xiang,Jia, Xiao-Dong
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- Highly diastereoselective inverse electron demand (IED) Diels-Alder reaction mediated by chiral salen-AlCl complex: The first, target-oriented synthesis of pyranoquinolines as potential antibacterial agents
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The first, target-oriented synthesis of pyranoquinolines as potential antibacterial agents by inverse electron demand (IED) Diels-Alder reaction using chiral salen-AlCl complex has been accomplished, the reactions proceed with moderate yields, and a very
- Magesh, Chinnian J.,Makesh, Sarasu V.,Perumal, Paramasivan T.
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- Halogen Bond-Catalyzed Povarov Reactions
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The use of a bidentate halogen bond donor to catalyse Povarov reactions of imines derived from aryl adehydes and anilines is reported. Dienophiles used in these reactions included 2,3-dihydrofuran, N-vinyl-2-pyrrolidone and N-Cbz-protected 2,3-dihydropyrr
- Liu, Xuelei,Toy, Patrick H.
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- Novel Use of Selectfluor for the Synthesis of cis-Fused Pyrano- and Furanotetrahydroquinolines
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Aryl imines formed in situ from aryl aldehydes and aromatic amines undergo smooth [4 + 2] cycloaddition reactions with cyclic enol ethers such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran in the presence of 10 mol % Selectfluor in acetonitrile at room tem
- Yadav,Reddy,Sunitha,Reddy
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- Sodium Salts of Anionic Chiral Cobalt(III) Complexes as Catalysts of the Enantioselective Povarov Reaction
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The sodium salts of anionic chiral cobalt(III) complexes (CCC?Na+) have been found to be efficient catalysts of the asymmetric Povarov reaction of easily accessible dienophiles, such as 2,3-dihydrofuran, ethyl vinyl ether, and an N-protected 2,3-dihydropyrrole, with 2-azadienes. Ring-fused tetrahydroquinolines with up to three contiguous stereogenic centers were thus obtained in high yields, excellent diastereoselectivities (endo/exo up to >20:1), and high enantioselectivities (up to 95:5 e.r.).
- Yu, Jie,Jiang, Hua-Jie,Zhou, Ya,Luo, Shi-Wei,Gong, Liu-Zhu
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- Stereoselective synthesis of pyrano[3,2-c]- and furano[3,2-c]quinolines: Gadolinium chloride catalyzed one-pot aza-Diels-Alder reactions
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A simple and efficient method for the cis-selective synthesis of pyrano- and furano[3,2-c]quinolines via gadolinium chloride catalyzed onepot aza-Diels-Alder reaction is described. Solvent conditions played amajor role in affecting the diastereoselectivity of the products.
- Yu, Yong,Zhou, Jun,Yao, Zhigang,Xu, Fan,Shen, Qi
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- Tungstophosphoric acid-catalyzed imino-diels-alder reaction: An efficient one-pot synthesis of pyrano-and furanoquinoline derivatives
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Tungstophosphoric acid has been found to be an efficient catalyst for the synthesis of pyranos-and furanoquinolines through the Imino-Diels-Alder reaction involving one-pot coupling of benzaldehydes, anilines, and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran.
- Das, Biswanath,Balasubramanyam,Krishnaiah, Maddeboina,Veeranjaneyulu, Boyapati
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- Catalysis with Supramolecular Carbon-Bonding Interactions
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Herein, we describe a new catalysis platform, supramolecular carbon-bonding catalysis, which exploits the highly directional weak interactions between carbon centers of catalysts and electron donors to drive chemical reactions. To demonstrate this catalys
- Li, Xinxin,Wang, Wei,Wang, Yao,Zhou, Pan-Pan
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- Controllable stereoselective synthesis of cis or trans pyrano and furano tetrahydroquinolines: Polyaniline-p-toluenesulfonate salt catalyzed one-pot aza-Diels-Alder reactions
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cis as well as trans pyrano tetrahydroquinolines were synthesized using a polymeric solid acid catalyst, polyaniline-p-toluenesulfonate (PANI-PTSA) salt, by conveniently controlling the reaction conditions. One-pot three component aza-Diels-Alder reaction
- Palaniappan, Srinivasan,Rajender, Boddula,Umashankar, Male
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- Dimensional Reduction of Lewis Acidic Metal-Organic Frameworks for Multicomponent Reactions
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Owing to hindered diffusions, the application of porous catalytic materials has been limited to relatively simple organic transformations with small substrates. Herein we report a dimensional reduction strategy to construct a two-dimensional metal-organic framework (MOF), Zr6OTf-BTB, with 96% accessible Lewis acidic sites as probed by the bulky Lewis base pivalonitrile. With nearly free substrate accessibility, Zr6OTf-BTB outperformed two three-dimensional MOF counterparts of similar Lewis acidity (Zr6OTf-BPDC and Zr6OTf-BTC) in catalyzing sterically hindered multicomponent reactions (MCRs) for the construction of tetrahydroquinoline and aziridine carboxylate derivatives with high turnover numbers (TONs). Zr6OTf-BTB was also superior to the homogeneous benchmark Sc(OTf)3 with nearly 14 times higher TON and 9 times longer catalyst lifetime. Furthermore, the topology-activity relationships in these Zr-based Lewis acidic MOFs were rationalized by comparing their Lewis acidity, numbers of Lewis acidic sites, and sterically accessible Lewis acidic sites. Zr6OTf-BTB was successfully used to construct several bioactive molecules via MCRs with excellent efficiency. This dimensional reduction strategy should allow the development of other MOF catalysts for synthetically useful and complicated organic transformations.
- Feng, Xuanyu,Song, Yang,Lin, Wenbin
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- PRODUCT DISTRIBUTION IN DIELS-ALDER ADDITION OF N-BENZYLIDENE ANILINE AND ENOL ETHERS
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The two diastereomeric products, all cis, and trans phenyl, form in highly variable ratio (up to a factor 20), depending on the conditions.
- Cabral, Jose,Laszlo, Pierre
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- Samarium triflate as mild and efficient catalyst for aza-diels-alder reaction: A facile synthesis of cis-fused pyrano-and furanoquinolines
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Three-component coupling reactions of aldehydes, amines, and cyclic enol ethers have been carried out in the presence of samarium triflate to afford the corresponding pyrano and furanoquinolines in excellent yields with high endo-selectivity. The reaction
- Narsaiah, A. Venkat,Reddy, A. Ramesh,Reddy, B. V. Subba,Yadav
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- Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza-Diels-Alder Cycloaddition
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Electrochemical synthesis of cyclic ether-annulated tetrahydroquinolines from imines and cyclic ethers in an undivided cell under constant current conditions was developed. The electrosynthesis proceeds via the enol ether formation from ethers following the aza-Diels-Alder [4+2] cycloaddition. The method is applicable to a wide range of imines and results in the desired products in yields of 23 to 75%. In situ preparation of imines from the corresponding anilines and aldehydes led to mostly the same yields of tetrahydroquinolines. No cycloaddition products were formed using the chemical oxidants. Synthesized cyclic ether-annulated tetrahydroquinolines exhibit high antifungal activity, which is superior to the commercial fungicide Triadimefon. (Figure presented.).
- Alekseenko, Anna L.,Baberkina, Elena P.,Glinushkin, Alexey P.,Grishin, Sergei S.,Kovalenko, Alexey E.,Terent'ev, Alexander O.,Vil', Vera A.
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supporting information
(2022/01/26)
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- One-pot cascade synthesis of pyrano/furanotetrahydroquinolines through povarov reaction catalyzed by Fe(NO3)3@Al2O3
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Fe(NO3)3@Al2O3 was synthesized as a green heterogeneous catalyst for Povarov reaction toward the one-pot cascade synthesis of cis- and trans-tetrahydroquinolines from aryl amines, aryl aldehydes, and electron-rich olefins (dihydropyran/dihydrofuran) under thermal conditions. The reaction is diastereoselective with trans product formed in preponderance. The products were characterized by 1H NMR, 13C NMR, IR, ESIMS, and elemental analysis. The characterization of Fe(NO3)3@Al2O3 was made by various techniques such as Fourier-transform infrared, inductively coupled plasma-atomic emission spectroscopy, X-ray diffraction, energy dispersive X-ray, scanning electron microscope, transmission electron micrographs, TGA, and vibrating sample magnetometer. High catalytic activity, easy recovery and reusability, eco-benign nature, and thermal and chemical stabilities are the key properties of the catalyst that makes it attractive from the viewpoint of green chemistry.
- Kaur, Ramneet,Khajuria, Rajni,Saini, Yeshwinder,Kapoor, Kamal K.
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- Synthesis method of 1, 2, 3, 4-tetrahydroquinoline derivatives
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The invention discloses a synthesis method of 1, 2, 3, 4-tetrahydroquinoline derivatives and belongs to the technical field of chemistry and chemical engineering. The synthesis method comprises that three components undergo a Povarov reaction in the prese
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Paragraph 0032; 0033
(2016/10/27)
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- The α-chymotrypsin-catalyzed Povarov reaction: One-pot synthesis of tetrahydroquinoline derivatives
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The three-component one-pot Povarov reaction for the synthesis of tetrahydroquinoline derivatives was catalyzed by α-chymotrypsin from bovine pancreas (BPC) for the first time. The products were obtained in moderate to good yields with a wide range of sub
- Li, Ling-Po,Cai, Xin,Xiang, Yang,Zhang, Yong,Song, Jian,Yang, Da-Cheng,Guan, Zhi,He, Yan-Hong
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p. 3148 - 3156
(2015/05/27)
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- Synthesis of pyranoquinolines via imino Diels-Alder reaction: Comparison of antibacterial efficacy of chirally separated individual diastereomers
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The first ever attempt to separate the four diastereomers formed during pyranoquinoline synthesis via imino Diels- Alder reaction mediated by chiral catalyst is successful. The comparison of the antibacterial efficacy of individual diastereomers is reveal
- Dhanapal, Ramu,Perumal, Paramasivan T.,Sridhar, Radhakrishnan
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p. 193 - 199
(2014/03/21)
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- Diethylaminosulfurtrifluoride-catalyzed efficient one-pot three-component aza-Diels-Alder reactions: A facile synthesis of substituted hexahydrofurano[3,2- c]quinolines
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The aza-Diels-Alder reactions of anilines in combination with substituted benzaldehydes and electron-rich cyclic alkenes have been investigated. The reactions have been carried out in the presence of catalytic amount of diethylaminosulfurtrifluoride in ac
- Dhanapal, Ramu,Perumal, Paramasivan T,Munusamy, Damodiran
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p. 553 - 559
(2013/06/26)
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- Niobium pentachloride catalyzed multicomponent povarov reaction
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A single-step method for the synthesis of furan- and pyranoquinoline derivatives through multicomponent Povarov reactions between aniline derivatives, benzaldehyde and two different enol ethers (2,3-dihydrofuran and 3,4-dihydropyran) using niobium pentach
- Da Silva, Bruno Henrique Sacoman Torquato,Martins, Lucas Michel?o,Da Silva-Filho, Luiz Carlos
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supporting information; experimental part
p. 1973 - 1977
(2012/09/22)
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- Chemoselective catalysis with organosoluble lewis acidic polyoxotungstates
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The preparation of new organosoluble Lewis acidic polyoxometalates (POMs) is reported. These complexes were prepared by the incorporation of Zr, Sc, and Y atoms into the corresponding monolacunary Dawson [P2W 17O61]10- and Keggin [PW11O 39]7- polyoxotungstates. The catalytic activity of these compounds was evaluated for C-C bond formation in the DielsAlder, Mannich, and Mukaiyama-type reactions. Comparisons with previously described Lewis acidic POMs are reported. Competitive reactions between imines and aldehydes or between various imines demonstrated that fine tuning of the reactivity could be reached by varying the metal atom in-corporated into the polyanionic framework. A series of experiments that employed pyridine derivatives allowed us to distinguish between the Lewis and induced Bronsted acidity of the POMs. These catalysts activate imines in a Lewis acidic way, whereas aldehydes are activated by indirect Bronsted catalysis.
- Dupre, Nathalie,Remy, Pauline,Micoine, Kevin,Boglio, Cecile,Thorimbert, Serge,Lacote, Emmanuel,Hasenknopf, Bernold,Malacria, Max
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supporting information; scheme or table
p. 7256 - 7264
(2010/09/04)
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- New findings on the cerium(IV) ammonium nitrate catalyzed Povarov reaction: Stereoselective synthesis of 4-alkoxy-2-aryl-1,2,3,4-tetrahydroquinoline derivatives
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Cerium(IV) ammonium nitrate catalyzes the three-component, imino Diels-Alder (Povarov) reaction between anilines, aromatic aldehydes, and acyclic vinyl ethers, giving cis-4-alkoxy-2-aryl-1,2,3,4-tetrahydroquinolines with almost complete diastereoselectivi
- Sridharan, Vellaisamy,Avendano, Carmen,Menendez, J. Carlos
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p. 1039 - 1044
(2008/12/22)
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- Synthesis of pyrano and furanoquinolines using silica chloride or amberlyst-15 as a heterogeneous catalyst
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The coupling of three components, anilines, benzaldehydes and 3,4-dihydro-2H- pyran or 2,3-dihydrofuran to prepare the corresponding pyrano or furanoquinolines has been achieved efficiently using silica chloride or Amberlyst-15 as a heterogeneous catalyst. Amberlyst-15 can be recovered and reused.
- Das, Biswanath,Reddy, Majjigapu Ravinder,Holla, Harish,Ramu, Ravirala,Venkateswarlu, Katta,Rao, Yerra Koteswara
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p. 793 - 795
(2007/10/03)
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- Photochemically catalysed Diels-Alder reaction of N-arylimines by 2,4,6-triphenylpyrylium salt: Synthesis of furo- and pyranoquinoline derivatives
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Photochemically promoted Diels-Alder reactions of N-arylimines with 2,3-dihydrofuran and 3,4-dihydro-2H-pyran were achieved by using 2,4,6-triphenylpyrylium tetrafluoroborate as a catalyst to produce the corresponding furo-and pyranoquinolines in high yield.
- Zhang, Wei,Guo, Yanping,Yang, Li,Liu, Zhong-Li
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p. 418 - 420
(2007/10/03)
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- Inter- and Intramolecular Imino Diels-Alder Reactions Catalyzed by Sulfamic Acid: A Mild and Efficient Catalyst for a One-Pot Synthesis of Tetrahydroquinolines
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The successful use of sulfamic acid as a catalyst in the inter- and intramolecular Inverse Electron Demand Diels-Alder reactions of iminodienes is described. A one-pot synthesis of tetrahydroquinolines was achieved by three component coupling of benzaldeh
- Nagarajan, Rajagopal,Magesh, Chinnan J.,Perumal, Paramasivan T.
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- Inverse electron demand Diels-Alder reactions of heterodienes catalyzed by potassium hydrogen sulfate: Diastereoselective, one-pot synthesis of pyranobenzopyrans, furanobenzopyrans and tetrahydroquinolines derivatives
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Potassium hydrogen sulfate catalyzes the one-pot three components coupling of aldehydes, anilines, and electron rich dienophiles such as dihydropyran, dihydrofuran, ethyl vinylether, and cyclopentadiene. With o-hydroxybenzaldehyde, the reaction probably p
- Kumar, R. Senthil,Nagarajan, Rajagopal,Perumal, Paramasivan T.
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p. 949 - 959
(2007/10/03)
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- SCHIZOID REACTIVITY OF N-BENZYLIDENE ANILINE TOWARD CLAY-CATALYZED CYCLOADDITIONS
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The K10/FeIII montmorillonite catalyzes cycloadditions of N-benzylidene aniline with vinyl ethers.Both and cycloadducts form.Tetrahydroquinolines and azetidines can thus be obtained.
- Cabral, Jose,Laszlo, Pierre,Montaufier, Marie Therese
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p. 547 - 550
(2007/10/02)
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- SYNTHESIS OF QUINOLINE DERIVATIVES BY CYCLOADDITION REACTION
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Synthesis of quinoline derivatives by Lewis acid catalyzed cycloaddition was investigated.
- Kametani, Tetsuji,Takeda, Hajime,Suzuki, Yukio,Honda, Toshio
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p. 499 - 506
(2007/10/02)
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