Regular Issue

Vol. 48, No. 4, 1998

20 data found. 1 - 20 listed
Communication | Regular issue | Vol 48, No. 4, 1998, pp. 617 - 620
Published online:
DOI: 10.3987/COM-97-8089
Synthesis and Antibacterial Activity of New, Non-natural 1β-Methylcarbapenem Bearing a σ-Symmetric Bicyclopyrazoliumthio Group as the Pendant Moiety

Yoshimitsu Nagao,* Satoshi Tamai, Noriko Tanigawa, Shigeki Sano, Toshio Kumagai*, and Ikuo Kishi

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan


Mercaptobicyclopyrazolium chloride (3) was successfully synthesized starting from pyrazole (4), and then exploited for the synthesis of new 1β-methylcarbapenem (2) which exhibits excellent antibacterial activities.

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Communication | Regular issue | Vol 48, No. 4, 1998, pp. 621 - 626
Published online:
DOI: 10.3987/COM-97-8098
Synthesis, Valence Isomerization, and Chemical Properties of 13-Azaazuleno-[1,2-g]bicyclo[4.3.1]deca-5b,6,8,10-tetraene

Tohru Takayasu, Yukihiko Tanaka, and Makoto Nitta*

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


1-Azaazulene-annulated tricyclo[,6]deca-2,4,7-triene ring system was synthesized, and 1H- and 13C-NMR spctroscopy suggested that the compound exists in equilibrium between major amount of 13-azaazuleno[1,2-g]bicyclo[4.3.1]deca-5b,6,8,10-tetraene and minor amount of 13-azaazuleno[1,2-g]tricyclo[,6]deca-5b,7,9-triene.

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Communication | Regular issue | Vol 48, No. 4, 1998, pp. 627 - 630
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DOI: 10.3987/COM-97-8101
A Novel Property of Reduced Benzodipteridine toward Molecular Oxygen

Hideaki Ohshiro, Norio Tamura, Akiko Arai, Koji Yamaguchi, Masaru Takanobu, Takashi Tominami, Shin-ichi Kondo, Tatsuya Nabeshima, Yumihiko Yano,* Jiro Toyoda, Kazuhiro Nakasuji, and Paul F. Heelis

*Department of Chemistry, Gunma University, 1-5-1 Tenjin-cho, Kiryu 376-8515, Japan


Reactivity of reduced benzodipteridine toward O2 was found to change dramatically, depending on the substituents at the N(3) and N(10) positions and pH in aqueous solution.

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Communication | Regular issue | Vol 48, No. 4, 1998, pp. 631 - 634
Published online:
DOI: 10.3987/COM-98-8111
First Construction of Benzotellurazepine Ring System, 4-Methoxy-1,5-benzotellurazepines

Haruki Sashida

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


o-Iodopropiolanilides (3) reacted with sodium hydrogen telluride to give 1,5-benzotellurazepinones (5) via intramolecular cyclization of the presumable phenyltellurole intermediates (4). The lactams (5) were converted into the title lactim compounds, 4-methoxy-1,5-benzotellurazepines (7) by treatment with trimethyloxonium tetrafluoroborate.

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Communication | Regular issue | Vol 48, No. 4, 1998, pp. 635 - 640
Published online:
DOI: 10.3987/COM-98-8123
Stereochemical Change in the Lewis Acid-promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue

Hidemitsu Uno,* Noboru Mizobe, Youtarou Yamaoka, and Noboru Ono

*Advanced Instrumentation Center for Chemical Analysis, Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan


In the presence of BF3·OEt2, the reaction of (3R)-5-t-butyldimethylsiloxy-6-methyl-3-phenyl-1H-pyrrolo[1,2-c]oxazole (3) with aliphatic aldehydes in ether occurred stereoselectively to give the corresponding (3R,7aR,1’R)-isomers (4a and 6a) as the major products, while the similar reaction with aromatic aldehydes afforded the (3R,7aR, 1’S)-isomers (7b, 8b, and 9b) predominantly. The product (7b) from the reaction with benzaldehyde was successfully transformed to a lactacystin analogue.

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 641 - 655
Published online:
DOI: 10.3987/COM-97-7949
Synthesis of 2,3-Disubstituted 4-Oxoquinolines and 3-Substituted Fused 4-Oxoquinolines

Hamad Z. Alkhathlan* and Khalid A. Al-Farhan

*Department of Chemistry, King Saud University, P.O. Box2455, Riyadh-11451, Saudi Arabia


Seven 2,3-disubstituted 4-oxoquinolines were prepared via two methods. In the first one 2,3-disubstituted 4-oxoquinolines were prepared via the condensation of 2-amino-α-cyanoacetophenone with substituted phthalic anhydrides, while in the second method the fused isoindolo[2,1-a]quinolines and pyrrolo[1,2-a]quinolines were first prepared and then converted to 4-oxoquinolines. X-Ray crystal structure analysis of ethyl 2-[3-cyano-4-oxo-2-quinolyl]benzoate is preported.

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 657 - 669
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DOI: 10.3987/COM-97-8027
Chloride-assisted Nitrolysis of Cyclic Tertiary Amines

Matthew D. Cliff

*Aeronautical and Maritime Research Laboratory, Deffence Science and Technology Organisation, P.O. Box 1500, Salisbury, SA 5108, Australia


The synthesis of nitramines from tertiary amine heterocycles via a chloride-assisted nitrolysis is presented. The process is effective for heterocyclic systems containing a single tertiary amine moiety and gives good to excellent yields for primary, secondary and tertiary alkyl leaving groups. Heterocyclic systems containing two tertiary amines are best nitrated via a tert-butyl leaving group, with other alkyl moieties leading to ring-opened species upon treatment with nitrating media both in the presence and absence of chloride ions.

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 671 - 678
Published online:
DOI: 10.3987/COM-97-8048
A Simple Preparation of Some 4-Methyl-2H-pyran-2-ones

Vladimir Kepe, Slovenko Polanc, and Marijan Kočevar*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SLO-1000 Ljubljana, Slovenia


A method for the preparation of substituted 4-methyl-2H-pyran-2-ones ( 6-19) starting from methyl ketones (1), N,N-dimethylacetamide dimethyl acetal (2) and N-acylglycines (4) in acetic anhydride is described.

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 679 - 686
Published online:
DOI: 10.3987/COM-97-8060
An Efficient and Stereoselective Conversion of Lactones to Substituted Cyclic Ethers

Hidemi Yoda,* Masato Mizutani, and Kunihiko Takabe

*Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan


A general route to substituted cyclic ethers has been described by using nucleophilic addition of Grignard reagents to lactones in the presence of CeCl3 followed by the Lewis acid-induced deoxygenation of the corresponding hemiketals with Et3SiH. Stereoselective reduction of the 5-membered adducts to the disubstituted tetrahydrofurans has been also investigated.

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 687 - 693
Published online:
DOI: 10.3987/COM-97-8070
Rearrangement of an N-Aryl-2-vinyltetrahydro-4-oxoquinoline to an Acridine Derivative

Claire Clémencin-Le Guillou, Sylviane Giorgi-Renault,* Jean-Charles Quirion,* and Henri-Philippe Husson

*Laboratoire de Chimie Thérapeutique associé au C.N.R.S., Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, avenue de l'Observatoire, 75270 Pairs Cedex 06, France


Acridine (4) has been obtained by acidic rearrangement of N-aryl-2-vinyltetrahydro-4-oxoquinoline (2). The mechanism involved a retro-Michael process followed by the attack of the electron rich aromatic ring onto the keto group.

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 695 - 702
Published online:
DOI: 10.3987/COM-97-8080
A Convenient Synthesis of 1,2,3-Triazoles Using Dichloroacetaldehyde

Katsumasa Harada,* Mizuho Oda, Akio Matsushita, and Masashi Shirai

*Ube Research Laboratory, UBE Indusries, Ltd., 1978-5 Kogushi, Ube Yamaguchi 755, Japan


1-Substituted 1,2,3-triazoles were prepared by the reaction of dichloroacetaldehyde tosyl- or mesylhydrazone with ammonia, amino derivatives, and hydrazine in good yield.

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 703 - 710
Published online:
DOI: 10.3987/COM-97-8095
Medicinal Foodstuffs. XIII. Saponin Constituents with Adjuvant Activity from Hyacinth Bean, the Seeds of Dolichos lablab L. (2): Structures of Lablabosides D, E, and F

Hajime Komatsu, Toshiyuki Murakami, Hisashi Matsuda, and Masayuki Yoshikawa*

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


Following the characterization of lablabosides A, B, and C, new oleanan-type triterpene bisdesmosides, lablabosides D, E, and F, were isolated from the glycosidic fraction with adjuvant activity obtained from the seeds of Dolichos lablab L. (Leguminosae). Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows: 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[6-O-(3-hydroxy-3-methylglutaroyl)-β-D-glucopyranosyl] 24-epi-hederagenin(lablabside D), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] 24-epi-hederagenin (lablabside E), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] oleanolic acid (lablabside F).

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 711 - 734
Published online:
DOI: 10.3987/COM-98-8105
Pyrylium Salts of γ-Thiapyrones --- A Simple Step to Phosphono-phosphino Substituted Pyridines and Pyridinium Salts

Richard Neidlein* and Dirk Uwe Hahn

*Pharmazeutisch-Chemishces Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 364, D-69120 Heidelberg, Germany


The phosphono-phoshino substituted γ-thiapyrones (1/2) are converted to pyrylium salts (3/4) with trimethyloxonium tetrafluoroborate (5) under mild conditions. Reaction of the pyrylium salts (3/4) with ammonia and primary amines (10) lead to phosphono-phoshino pyridines (6/7) and pyridinium salts (8/9).

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Paper | Regular issue | Vol 48, No. 4, 1998, pp. 735 - 741
Published online:
DOI: 10.3987/COM-98-8109
Dimerization of 1-Benzenesulfonyl-3-cyanomethylindole. Synthesis of Indole[2,3-a]carbazoles

Egle M. Beccalli,* Maria Luisa Gelmi, and Emanuela Erba

*Instituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi di Milano, Via Venezian 21, I-20133 Milano, Italy


The treatment of 1-benzenesulfonyl-3-cyanomethylindole (1) with LDA, in THF at 0 °C, affords 2-(1-benzenesulfonyl-1H-indol-3-yl)-3-(1H-indol-3-yl)acrylonitrile (2) in 79% yield. From 2, the indolo[2,3-a]carbazole (4) has been obtained in 58% yield.

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Note | Regular issue | Vol 48, No. 4, 1998, pp. 743 - 747
Published online:
DOI: 10.3987/COM-97-7886
Synthesis of 1,3-Dialkyl- and 1,3-Diphenyl-5-cyano-2-thiouracil Derivatives

Lars F. Jalander* and Jan-Erik Lönnqvist

*Department of Organic Chemistry, Abo Akademi University, Biskopsgatan 8, FIN-20500 Abo, Finland


Nucleophilic vinylic substitutions of ethyl (E)- and (Z)-3-aryl-3-chloro-2-cyanopropenoates (1a) and (1b) with symmetrically substituted thioureas afforded, after spontaneous cyclisation, 1,3-dialkyl- and 1,3-diphenyl-5-cyano-2-thiouracil derivatives (3a-3h) in moderate to good yields.

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Note | Regular issue | Vol 48, No. 4, 1998, pp. 749 - 754
Published online:
DOI: 10.3987/COM-97-8077
Electrochemical Synthesis of 2,1-Benzisoxazoles by Controlled Potential Cathodic Electrolysis

Byeong Hyo Kim,* Young Moo Jun, Yong Rack Choi, Doo Byung Lee, and Woonphil Baik

*Department of Chemistry, Kwangwoon University, 447-1, Wolgye-Dong Nowon-ku, Seoul, 139-701, Korea


Using a divided cell, reductive cyclization of nitroarene compounds into 2,1-benzisoxazoles in mild conditions was successfully accomplished by the controlled potential cathodic electrolysis reactions. Optimum reaction potential of each reaction was determined based on cyclic voltametric behavior in methanol solution at Pb or Pt cathode, and Pt anode.

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Note | Regular issue | Vol 48, No. 4, 1998, pp. 755 - 767
Published online:
DOI: 10.3987/COM-97-8083
Reaction of Proflavine Derivatives with Formaldehyde: Access to Mono- and Bis-(3,4-dihydro[1,3]oxazino)acridines of Pharmacological Interest

Noémie Fixler, Martine Demeunynck,* Alain Duflos, and Jean Lhomme*

*Ledss/UMR 5616, Université Joseph Fourier, 38041 Grenoble cédex 9, France


Proflavine derivatives react with formaldehyde in acidic media to give 3,4-dihydro[1,3]oxazino condensed compounds. Depending on the nature of the solvents and the substituents attached to the exocyclic nitrogens, mono and bis reaction can occur.

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Note | Regular issue | Vol 48, No. 4, 1998, pp. 769 - 773
Published online:
DOI: 10.3987/COM-97-8085
Reinvestigation of Reaction of cis-Aziridinyl Ketone Semicarbazones and Tosylhydrazones with Diethyl Ether-Boron Trifluoride(1/1)

Motonobu Morioka* and Tsuyoshi Ogata

*Department of Material science and chemical Engineering, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan


A previously reported skeleton of reaction products of cis-1-alkyl-3-phenyl-aziridin-2-yl phenyl ketone semicarbazones (1) and tosyl hydrazones (2) with diethyl ether—boron trifluoride (1/1) was corrected to 2,3,4,5-tetrahydro-1,2,4-triazine derivatives (3) and (4), based on the results of reinvestigation with the X-Ray crystallography.

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Note | Regular issue | Vol 48, No. 4, 1998, pp. 775 - 778
Published online:
DOI: 10.3987/COM-97-8086
A Facile and Convenient Synthesis of 9-Methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one Potassium

Atsunori Sano* and Masami Ishihara

*Tokyo Research Laboratories, Wako Pure Chemical Ind., Ltd., 1633 Matoba, Kawagoe, Saitama 350-1101, Japan


Two convenient synthetic methods of anti-allergy agent, 9-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one potassium (1a), are described. Heating of a mixture of malononitrile (2b), 2-amino-3-picoline (4), ethyl orthoformate, and sodium azide in acetic acid, followed by hydrolysis with hydrochloric acid gave 9-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (1b) which was led to 1a by treatment with potassium hydroxide. The use of ethyl cyanoacetate (2a) instead of 2b afforded ethyl 3-(3-methyl-2-pyridylamino)-2-(1H-tetrazol-5-yl)acrylate (8) which was also led to 1a by treatment with potassium hydroxide.

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Note | Regular issue | Vol 48, No. 4, 1998, pp. 779 - 785
Published online:
DOI: 10.3987/COM-98-8102
A Convenient One-Pot Synthesis of 6-Trifluoromethylpyridines

Isamu Katsuyama, Seiya Ogawa, Hiroko Nakamura, Yoshihiro Yamaguchi, Kazumasa Funabiki, Masaki Matsui, Hiroshige Muramatsu, and Katsuyoshi Shibata*

*Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagito, Gifu, Gifu 501-1193, Japan


α,β-Unsaturated trifluoromethyl ketones (1) react with primary enamines (2) such as β-aminocrotononitrile and β-aminocrotonates in the presence of phosphorus oxychloride / pyridine adsorbed on silica gel and manganese dioxide, providing good to high yields of 6-trifluoromethylpyridines (5).

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20 data found. 1 - 20 listed