Special Issue

Sho Ito's Special Issues, Vol. 54, No. 1, 2001

58 data found. 31 - 58 listedFirst Previous
Paper | Special issue | Vol 54, No. 1, 2001, pp. 225 - 235
Published online:
DOI: 10.3987/COM-00-S(I)20
Bis(ethylenethio)tetraselenafulvalene and Related Hybrid Diselenadithiafulvalenes as Novel Electron Donors Forming Highly Conductive Complexes with 7,7,8,8-Tetracyanoquinodimethane

Mie Kodani, Satoshi Murakami, Tetsuya Jigami, Kazuo Takimiya, Yoshio Aso, and Tetsuo Otsubo*

*Department of Applied Chemistry, Faculty of Engineering, Hiroshima University, Higashi-hiroshima, Hiroshima 739-8527, Japan


The title tetraselenafulvalene (BET-TSF) and four related hybrid diselenadithiafulvalenes (STF) have been synthesized as a five-membered heterocycle-fused tetrathiafulvalene type of novel electron donors, which form highly conducting molecular complexes with 7,7,8,8-tetracyanoquinodimethane. In particular, the complex of BET-TSF shows a room-temperature conductivity of 2600 S cm—1, which is of the highest class for a molecular complex.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 237 - 248
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DOI: 10.3987/COM-00-S(I)21
Thermolysis of Ethoxycarbonyl[2-phenyl-2-(phenylsulfonylhydrazono)ethyl]methylenetriphenylphosphoranes. Formation of Substituted Pyridazinones

Suketaka Ito,* Akikazu Kakehi, Kyoko Okada,1 and Ikuko Shibazaki

*Depatment of Indusrial Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan


Ethoxycarbony[2-phenyl-2-(phenylsulfonylhydrazono)ethyl]methylenetriphenylphosphoranes were prepared by the reaction of ethoxycarbonymethylenetriphenylphosphorane with phenylsulfonylhydrazones of phenacyl bromides. Thermolysis of the phosphoranes gave 6-phenyl-2-phenylsulfonyl-3(2H)-pyridazinones, 6-phenyl-4-phenylsulfonyl-3(2H)-pyridazinones, and 6-phenyl-2-phenylsulfonyl-4-triphenylphosphoranylidene-1,4-dihydro-3(2H)-pyridazinones, together with triphenylphosphine. The structure of disubstituted methylenetriphenylphosphorane was confirmed by an X-Ray diffraction method.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 249 - 257
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DOI: 10.3987/COM-00-S(I)22
[22]Metacyclophanedienes with Furan Bridges

Reginald H. Mitchell,* Timothy R. Ward, and Yunxia Wang

*Department of Chemistry, University of Victoria, P.O. Box 3065, Victoria, BC V8W 3V6, Canada


[22]Metacyclophanedienes with either one furan and one benzene or two furans on the bridges are thermally stable and do not convert to their isomeric dihydropyrenes, unlike the compounds with one furan or one benzene on the bridge.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 259 - 274
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DOI: 10.3987/COM-00-S(I)26
Total Syntheses of Plagiochins A and D, Macrocyclic Bis(bibenzyls), by Pd(0) Catalyzed Intramolecular Stille-Kelly Reaction1

Yoshiyasu Fukuyama,* Hideyuki Yaso, Takashi Mori, Hironobu Takahashi, Hiroyuki Minami, and Mitsuaki Kodama

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-machi, Tokushima, 770-8514, Japan


Total syntheses of plagiochins A (1) and D (4), the former of which exhibits a significant neurotrophic activity, have been accomplished. The key 16-membered ring closure in 4 has been achieved directly from the dibromoperrottetin derivative (7) by Pd(0) catalyzed intramolecular Stille-Kelly reaction, whereas 1 has been synthesized from the dibromide (28) via the trimethylstannyl compounds (29) and (30) by Pd(0) catalyzed intramolecular Stille reaction.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 275 - 282
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DOI: 10.3987/COM-00-S(I)29
Azepine and [1,3]Oxazepine Fused Ring Construction through a Cationic Cyclization: an N-acyliminium Ion Trapping of an Oxygen Atom or Olefin

Aïcha Mamouni, Adam Daïch, Stefan Marchalin, and Bernard Decroix

*Laboratoire de Chimie, URCOM, Faculté des Sciences et Techniques, Université du Havre, 25 Rue Philippe Lebon, B.P. 540 76058 Le Havre Cedex, France


Carbophilic addition on (and/or sodium borohydride reduction of) an imide ester functionality (3) proceeds with extremely high regioselectivety to produce bifunctionalized hydroxy-ω-carbinol lactam products (4) and (8). These species could act as N-acyliminium ion precursors and, via an O-cationic or π-cationic cyclization, and they led regioselectively in high yields to fused triheterocyclic azepine (11) or [1,3]oxazepine (18).

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 283 - 290
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DOI: 10.3987/COM-00-S(I)30
A Convenient Determination of Chiral Pteridines; Application of Fluorescence Detected Circular Dichroism (FDCD) to the Major Pterin from Escherichia coli

Takashi Sugimoto,* Kazuhisa Ikemoto, Shizuaki Murata, Masahiro Tazawa, Takahide Nomura, Yasumichi Hagino, Hiroshi Ichinose, Toshiharu Nagatsu, and Akio Wada

*Graduate School of Human Informatics, Nagoya University, Nagoya 464-8601, Japan


The major pterin from Escherichia coli was determined as L-monapterin, by applying fluorescence detected circular dichroism (FDCD). FDCD was highly sensitive and specific to fluorescent chiral pterin, and allowed structure determination even in the presence of non-fluorescent contaminants.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 291 - 299
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DOI: 10.3987/COM-00-S(I)32
1,3-Dipolar Cycloadditions of 3-Bromo-1,5- and 3-Bromo-1,7-azulenequinones with Diazomethane, Diphenylnitrilimine, and Benzonitrile Oxide

Yong Zhe Yan, Katsuji Hirowatari, Kanji Kubo, Nobuo Kato, Akira Mori,* Hitoshi Takeshita,1 and Tetsuo Nozoe

*Instituete of Advanced Material Study, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


The reactions of 3-bromo-1,5- and 3-bromo-1,7-azulenequinones with diazomethane gave cyclooctatrienone derivatives and a [4+2] 1,3-dipolar adduct while they reacted with diphenylnitrilimine and benzonitrile oxide to give the corresponding [4+2] 1,3-dipolar adducts, showing the different site selectivities. 3-Bromo-1,5-azulenequinone reacted with the 1,3-dipoles dominantly to form the adducts on the cyclopentenone part while 3-bromo-1,7-azulenequinone reacted on the seven-membered ring.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 301 - 308
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DOI: 10.3987/COM-00-S(I)33
Xanthate Mediated Generation of the Benzotriazol-1-yl-methyl Radical and Its Subsequent Addition to a Variety of Olefins

Alan R. Katritzky,* Martin A. C. Button, and Sergey N. Denisenko

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


The first generation of the benzotriazol-1-ylmethyl radical (3) is reported from S-(1H-1,2,3-benzotriazol-1-ylmethyl)-O-ethylcarbonodithioate (1). Subsequent additions of radical (3) to a variety of olefins are demonstrated.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 309 - 317
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DOI: 10.3987/COM-00-S(I)37
Preparation of β-Substituted γ-Keto Esters by the Grignard Reaction on N-Acylpyrazoles

Choji Kashima,* Yoshie Shirahata, and Yoshihiro Tsukamoto

*Department of Chemistry, University of Tsukuba, Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


Various γ-keto esters were prepared by either the alcoholysis of N-(4-oxoalkanoyl)pyrazoles or the Grignard replacement of pyrazole moiety of 4-(N-pyrazolyl)-4-oxoalkanoic esters. By using 3-phenyl-l-menthopyrazole as a chiral auxiliary, β-substituted γ-keto esters were enantioselectively obtained.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 319 - 328
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DOI: 10.3987/COM-00-S(I)40
Revision of the Structure of a New Coumarin Isolated from Artemisia carviforia Wall

Takashi Harayama,* Keiko Katsuno, Yoshitaka Nishita, Masako Fujii, Hitoshi Abe, and Yasuo Takeuchi

*Faculty of Pharmaceutical Science, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


Four coumarins (1-4) were synthesized by the routes shown in Schemes 2-5, respectively. The previously proposed structure for a new coumarin isolated from Artemisia carviforia was incorrect; the structure of the coumarin is represented by formula (3).

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 329 - 339
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DOI: 10.3987/COM-00-S(I)45
Reductive Cyclization of 8-(2-Nitrophenyl)-1-azaazulene Derivatives; Formation of 6a,7-Diazanaphth[3,2,1-cd]azulene and 7H-1,7-Diazaindeno[1,2-e]azulene Systems, a New DNA Intercalater

Noritaka Abe,* Maki Nabeshima, Hiroyuki Fujii, Akikazu Kakehi, Yuichi Kageura, and Takeo Konakahara

*Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753-8512, Japan


Reaction of ethyl 2-dimethylamino-8-(2-nitrophenyl)-1-azaazulene-3-carboxylate with hexamethylphosphorous triamide gave ethyl 6-dimethylamino-6a,7-diazanaphth[3,2,1-cd]azulene-5-carboxylate (7b) and ethyl 2-dimethylamino-7H-1,7-diazaindeno[1,2-e]azulene-3-carboxylate (8b). The structures of 7b and 8b were determined by X-Ray structure analyses. Compound (8b) was intercalated to Calf-Thymus DNA and a 12-mer DNA with binding constants KD = 1.55 x 106 and 1.75 x 106 M-1, respectively.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 341 - 350
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DOI: 10.3987/COM-00-S(I)53
Diastereoselective Addition of Organometallic Reagents to (R)-2,3-Isopropylidenedioxy-1-(2-furyl)-1-propanone Yielding Chiral Tertiary Furyl Carbinols

Masayoshi Tsubuki,* Naohiro Tarumoto, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


The nucleophilic addition of either organolithium or Grignard reagents to (R)-2,3-isopropylidenedioxy-1-(2-furyl)-1-propanone (1) in Et2O afforded the corresponding anti isomers predominantly, whereas addition of organolithium reagents in THF with HMPA as a co-solvent gave the syn isomers in moderate selectivities.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 351 - 358
Published online:
DOI: 10.3987/COM-00-S(I)54
Synthesis and Mercurophilic Properties of Acyclic and Thiolariat Ethers Having a Tropone Pendant

Kanji Kubo* and Akira Mori*

*Instituete of Advanced Material Study, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


Acyclic and thiolariat ether derivatives (3 and 4) having a tropone pendant were synthesized. Acyclic and thiolariat ether (3, 4a and 4b) were used as carriers for transport of Hg2+ through a chloroform liquid membrane. Thiolariat (4c) did not transport from source phase to receiving phase of Hg2+, but extracted into chloroform layer. Effective Hg2+ extractability of 4c was a result of the synergistic coordination of oxygen and sulfur atoms of the thiolariat ether.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 359 - 375
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DOI: 10.3987/COM-00-S(I)55
Quinolone Analogues 3. Synthesis of 1,3-Dialkyl-4-oxo-1,4-dihydropyridazino[3,4-b]quinoxalines

Yoshihisa Kurasawa,* Shinichi Ohshima, Yaeko Kishimoto, Miharu Ogura, Yoshihisa Okamoto, and Ho Sik Kim

*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan


The 1-alkyl-3-methyl-4-oxo-1,4-dihydropyridazino[3,4-b]quinoxalines (10a-d) were synthesized from the quinoxaline N-oxides (8a-d) via the oxidation of the 4-acetyl-1-alkyl-3-methyl-1,5-dihydropyridazino[3,4-b]quinoxalines (9a-d) with N-bromosuccinimide/water, sodium bromate, or selenium dioxide, while the 1-alkyl-3-ethyl-4-oxo-1,4-dihydropyridazino[3,4-b]quinoxalines (13a-d) were synthesized from the quinoxaline N-oxides (8a-d) via the oxidative ring transformation of the 1-alkyl-3-ethyl-2,3-dihydro-4-hydroxy-1H-1,2-diazepino[3,4-b]quinoxalines (12a-d), respectively.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 377 - 385
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DOI: 10.3987/COM-00-S(I)56
Preparation, Structure, and Properties of 1,3-Bis(1,4-dithiafulven-6-yl)azulenes

Akira Ohta,* Kyoko Yamaguchi, Naoki Fujisawa, Yoshiro Yamashita, and Kunihide Fujimori*

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi, Matsumoto 390-8621, Japan


Novel bis(1,3-dithiole) donors containing an azulene spacer unit have been prepared from 1,3-diformylazulene using a Wittig—Horner reaction. The cyclic voltammetry revealed that they are stronger electron donors than tetrathiafulvalene and show amphoteric characters. The structural features of a benzo-fused derivative were investigated by an X-Ray analysis. The spectroelectro-chemical studies on the methylthio derivative revealed that the cation radical and dication state show the longest absorption maxima at 612 and 721 nm, respectively.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 387 - 394
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DOI: 10.3987/COM-00-S(I)60
Generation and Amphoteric Redox Properties of Novel Neutral Radicals with the TTF-TCNQ Hybrid Structure1

Takanori Suzuki,* Masahiro Yamada, Masakazu Ohkita, and Takashi Tsuji

*Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan


One electron oxidation of 4-(2-tetrathiafulvalenyl)phenyl substituted dicyanomethylides (1-) gave black solids of the title radicals (1·). They exhibit quite high electrochemical amphotericity, which may be responsible for their good electrical conductivities (σ = ca. 10-7 S cm-1) as a single component. Isomeric radicals (2·) with a m-phenylene spacer could not be obtained under the similar conditions probably due to insufficient delocalization of the unpaired electron.

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Paper | Special issue | Vol 54, No. 1, 2001, pp. 395 - 404
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DOI: 10.3987/COM-00-S(I)70
Lewis Acid Catalysis of Second-Generation Metallosalen Complexes: an Explanation for Stereochemistry of Asymmetric Hetero Diels-Alder Reaction

Jun Mihara, Kohsuke Aikawa, Tatsuya Uchida, Ryo Irie, and Tsutomu Katsuki*

*Department of Chemistry, Faculty of Science, Graduate School, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan


Chloro nitrosyl (R,S)-(salen)ruthenium(II) complex served as a good catalyst for asymmetric hetero Diels-Alder (HDA) reaction of Danishefsky's diene with a wide variety of aldehydes. In contrast with this, (R,R)-(salen)-chromium(III) and -manganese(III) complexes well catalyze HDA reaction of simple aldehydes, while (R,S)-(salen)-chromium(III) and -manganese(III) complexes better catalyze HDA reaction of aldehydes bearing a precoordinating group. These features of metallosalen-catalyzed HDA reactions were rationalized by assuming that HDA reaction of aldehydes bearing a precoordinating group would proceed through aldehyde-metallosalen complex which takes cis-β-structure.

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Note | Special issue | Vol 54, No. 1, 2001, pp. 405 - 410
Published online:
DOI: 10.3987/COM-99-S(I)3
Optical Resolution of 2-azabicyclo[2.2.1]hept-5-en-3-one by Inclusion Complexation with Brucine

Koichi Tanaka, Masako Kato, and Fumio Toda*

*Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Okayama 700-0005, Japan


A simple optical resolution method of 2-azabicyclo[2.2.1]hept-5-en-3-one by inclusion complexation with brucine was reported. The crystal structure of the inclusion complex was analyzed by X-Ray diffraction in order to elucidate the mechanism of the efficient chiral recognition in the inclusion crystals.

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Note | Special issue | Vol 54, No. 1, 2001, pp. 411 - 418
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DOI: 10.3987/COM-99-S(I)4
Synthesis of New Chiral Catalysts, 2-Azanorbornyloxazolidines, for Enantioselective Addition of Diethylzinc to Aldehydes

Hiroto Nakano,* Yuko Okuyama, Kazuto Iwasa, and Hiroshi Hongo*

*Tohoku Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan


Optically active 2-azanorbornyloxazolidines were prepared from 2-azanorbornylmethanols and catalyzed the enantioselective addition of diethylzinc to aldehydes to give optically active secondary alcohols.

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Note | Special issue | Vol 54, No. 1, 2001, pp. 419 - 424
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DOI: 10.3987/COM-00-S(I)11
Synthesis of 2,5-Disubstituted Tetrahydrofurans Catalyzed by Palladium(0)

Osamu Hara,* Kazushige Fujii, Yasumasa Hamada, and Youji Sakagami

*Faculty of Pharmaceutical Sciences, Chiba University, Inage-ku, Chiba 263-8522, Japan


A stereoselective cyclization of an allylic ester to 2,5-disubstituted tetrahydrofurans catalyzed by palladium(0) is demonstrated. In this cyclization, acetoxy heptenol (6a) having a free hydroxy group prefered trans isomer to cis isomer. By the use of the protected acetoxy heptenol (6b), the cis selectivity was observed. The stereoselectivity was enhanced by the use of DPPIO ligand.

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Note | Special issue | Vol 54, No. 1, 2001, pp. 425 - 432
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DOI: 10.3987/COM-00-S(I)12
Syntheses of Wasabi Phytoalexin (Methyl 1-Methoxyindole-3-carboxylate) and Its 5-Iodo Derivative, and Their Nucleophilic Substitution Reactions1

Masanori Somei,* Asuka Tanimoto, Hitomi Orita, Fumio Yamada, and Toshiharu Ohta

*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


A simple synthetic method for methyl 1-methoxyindole-3-carboxylate, a phytoalexin isolated from Wasabia japonica, syn. Eutrema wasabi, and its 5-iodo derivative is reported. They underwent nucleophilic substitution reactions selectively at the 2-position.

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Note | Special issue | Vol 54, No. 1, 2001, pp. 433 - 436
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DOI: 10.3987/COM-00-S(I)43
Alternative Synthesis of B/C-cis Hexahydrobenzo[c]phenanthridine from 2-Phenyl-1-tetralone

Makoto Yoshida, Toshiko Watanabe, and Tsutomu Ishikawa*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


A B/C-cis hexahydrobenzo[c]phenanthridine (7) was alternatively prepared by the hydride-reduction of a tetrahydrobenzo[c]phenanthridine derivative (6) under acidic condition, which was derived from 2-phenyl-1-tetralone oxime (3) through four steps (reductive amidation, methylation, Bischler-Napieralski cyclization, and hydride reduction).

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Note | Special issue | Vol 54, No. 1, 2001, pp. 437 - 438
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DOI: 10.3987/COM-00-S(I)44
Triphosgene: a Versatile Reagent for Bischler-Napieralski Reaction

Tatsuru Saito, Makoto Yoshida, and Tsutomu Ishikawa*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Triphosgene causes direct formation of quaternary benzo[c]phenanthridines such as anti-tumor active nitidine (2a) chloride by Bischler-Napieralski reaction of 2-phenyl-1-(N-methylformamido)naphthalenes under heating in acetonitrile.

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Note | Special issue | Vol 54, No. 1, 2001, pp. 439 - 444
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DOI: 10.3987/COM-00-S(I)57
Preparation of Azulenequinones Containing Azacrown Moieties and the Singular Complexation of Sodium or Potassium Cation by 3,5-Bis(aza-18-crown-6)-1,7-azulenequinone in Solution

Ohki Sato, Noriko Matsuda, and Josuke Tsunetsugu*

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan


Efficient syntheses of azulenequinones containing azacrown ether moieties as pendants (2)–(5) were carried out. The singular complexation properties of 3,5-bis(aza-18-crown-6)-1,7-azulenequinone (5b) with sodium or potassium cation were investigated by 1H NMR measurement.

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Review | Special issue | Vol 54, No. 1, 2001, pp. 445 - 474
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DOI: 10.3987/REV-00-SR(I)2
Nucleophilic Aromatic Substitution of Hydrogen as a Tool for the Synthesis of Indole and Quinoline Derivatives

Mieczyslaw Makosza* and Krzysztof Wojciechowski

*Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warszawa 42, P.O.Box 58, Poland


Indole and quinoline belong to the most important heterocyclic systems. Although there are numerous methods of syntheses of these heterocycles, new processes leading to these systems have still attracted considerable attention. Nucleophilic Aromatic Substitution of Hydrogen in nitroarenes and other electrophilic arenes opens new rich possibilities for synthesis of indole and quinoline derivatives. In this review a variety of methods for synthesis of these heterocycles based on the initial nucleophilic substitution of hydrogen are discussed.

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Review | Special issue | Vol 54, No. 1, 2001, pp. 475 - 496
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DOI: 10.3987/REV-00-SR(I)3
Photochemical Dimerization in Solution of Heterocyclic Substituted Alkenes Bearing an Electron Withdrawing Group

Maurizio D'Auria

*Dipartamento di Chimica, Università della Basilicata, Via N. Sauro 85, 85100 Potenza, Italy


The photochemical dimerization in solution of heterocycle substituted alkenes bearing electron withdrawing groups is reported. The reactions occurred both in the singlet and in the triplet states showing good regio- and stereoselectivities. The regioselectivity can be explained assuming that the dimerization reaction is frontier orbitals controlled. The stereoselectivity can be explained assuming the formation of the most stable isomers

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Review | Special issue | Vol 54, No. 1, 2001, pp. 497 - 528
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DOI: 10.3987/REV-00-SR(I)6
The Structural Aspects of Carbapenem Antibiotics

Makoto Sunagawa* and Akira Sasaki

*Sumitomo Pharmaceuticals Research Center, 1-98, Kasugadenaka 3-chome, Konohana-ku, Osaka 554-0022, Japan


The discovery of thienamycin in 1976 caused much synthetic research effort to be concentrated on carbapenem antibiotics, by many groups. To date, two carbapenems, which need to be coadministered with other drugs, and then a new generation carbapenem, which could be utilized as a single agent, were developed for clinical use based on the progress of synthetic chemistry. Today, attention has been focused on the development of next generation carbapenem antibiotics. These trends of the carbapenem antibiotics developed in last quarter century are reviewed from a viewpoint of their chemical structures.

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Review | Special issue | Vol 54, No. 1, 2001, pp. 529 - 559
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DOI: 10.3987/REV-00-SR(I)7
Biotransformation of Terpenoids from the Crude Drugs and Animal Origin by Microorganisms

Toshihiro Hashimoto, Yoshiaki Noma, and Yoshinori Asakawa*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-machi, Tokushima, 770-8514, Japan


Terpenoids, dehydrocostuslactone (2), costunolide (3), α-, β-, and γ-cyclocostunolides (4~6), α-santonin (7) and atractylon (8) isolated from the crude drugs and (-)-ambrox (9) from animal origin were biotransformed by Aspergillus niger, A. cellulosae, and Botryospaeria dothidea etc. to afford the structurally interesting metabolites. Their stereostructures were established by a combination of high-resolution NMR spectrum, X-Ray crystallographic analysis and chemical reaction. The metabolic pathways of terpenoids by A. niger resembled those by mammals, but are quite different from those by A. cellulosae.

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