Regular Issue

Vol. 57, No. 9, 2002

14 data found. 1 - 14 listed
Communication | Regular issue | Vol 57, No. 9, 2002, pp. 1587 - 1590
Published online:
DOI: 10.3987/COM-02-9539
Intermolecular Photoreaction of Arenecarbothioamide with 3-Methyl- and 2,4-Dimethylfurans: a Novel Formation of 2-Arylthiophene Derivatives through Photoinduced Reaction

Kazuaki Oda,* Hisao Tsujita, and Minoru Machida*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


Photoreaction of arenecarbothioamides (1) with 3-methylfuran (2) in benzene-acetone mixed solvent gave 5-aryl-2,3-dihydrothiophene derivatives (3) accompanied by pyrrole compounds.

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Communication | Regular issue | Vol 57, No. 9, 2002, pp. 1591 - 1597
Published online:
DOI: 10.3987/COM-02-9559
Asymmetric Photocyclizations of Chiral Auxiliary-substituted N-Acyl-α-dehydroamino Acids into 1,2-Dihydrobenzoquinolinone Derivatives

Kei Maekawa,* Tetsutaro Igarashi, Kanji Kubo, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering
Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan


The irradiation of the title compounds [(Z)-1] with an (S)-alanine auxiliary in methanol containing a tertiary amine afforded a diastereomeric mixture of (S,S)- and (R,S)-1,2-dihydrobenzo[f]quinolinones, along with (E)-1, benzo[f]isoquinoline, and 1-azetine derivatives. It was found that electron transfer-initiated photocyclizations of (Z)-1 in polar solvents give (S,S)-1,2-dihydrobenzoquinolinones in diastereomeric excess whose value varies from 0 to 55% depending on the properties of the amine and solvent employed.

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Paper | Regular issue | Vol 57, No. 9, 2002, pp. 1599 - 1614
Published online:
DOI: 10.3987/COM-02-9484
A New General Route to Novel Azomethine Ylides for Cycloaddition Reactions

François-Xavier Lery, Nicole Kunesch, Pascal George, and Henri-Philippe Husson*

*Laboratoire de Pharmacognosie,UMR 8638 associee au CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, Avenue de l’Observatoire, 75270 Paris Cedex, France


A general method providing access to stabilized azomethine ylides generated from substituted 1,3- and 3,1-aryloxazines was developed. A two-step sequence based on 1,3-dipolar cycloaddition reactions with N-arylmaleimides was elaborated to give a series of highly substituted pyrrolopyrrolidines in good yields.

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Paper | Regular issue | Vol 57, No. 9, 2002, pp. 1615 - 1626
Published online:
DOI: 10.3987/COM-02-9514
On Selective Functionalization of meso-Tetraphenylporphyrin Derivatives by Vicarious Nucleophilic Substitution of Hydrogen

Stanislaw Ostrowski,* Agnieszka Mikus, Young Key Shim, Jong-Cheol Lee, Eun-Young Seo, Kee-In Lee, and Marian Olejnik

*Institute of Chemistry, University of Podlasie, ul. 3-go Maja 54, 08-110 Siedlce, Poland


The studies on selective derivatization of meso-tetraphenylpor-phyrin (TPP) using nitration and Vicarious Nucleophilic Substitution of Hydrogen (VNS) are reported. TPP, its metal complexes and N,N-dimethyl substituted derivatives do not enter the VNS reaction. On the other hand, meso-substituted TPP results in the mono-nitration of one phenyl ring and the intermediate obtained, after simple transformation to its metal complex, reacts with carbanions bearing leaving groups at the carbanionic center, according to VNS scheme. This gives new opportunities for the peripheral functionalization of porphyrins. In this work the copper and zinc complexes were investigated.

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Paper | Regular issue | Vol 57, No. 9, 2002, pp. 1627 - 1634
Published online:
DOI: 10.3987/COM-02-9533
Synthesis of Analogs of Wasabi Phytoalexin (Methyl 1-Methoxyindole-3-carboxylate)

Koji Yamada, Yukiko Kanbayashi, Saori Tomioka, and Masanori Somei*

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


Syntheses of wasabi phytoalexin analogs, such as 6-bromo-5-iodo, 2-bromo-5-iodo, 6-nitro, 5-chloroacetyl, and 6-chloroacetyl congeners, are reported. An interesting effect of the 1-methoxy group on the regioselectivity of electrophilic substitution reactions on indole nucleus is observed.

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Paper | Regular issue | Vol 57, No. 9, 2002, pp. 1635 - 1643
Published online:
DOI: 10.3987/COM-02-9537
Synthesis of 2- and 3-Benzoylindoles by Friedel-Crafts Reaction of Indole-2,3-dicarboxylic Anhydrides with Anisoles

Yasuyoshi Miki,* Yasuhiko Tsuzaki, Chika Kai, and Hiroko Hachiken

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan


Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with anisole in the presence of titanium(IV) chloride gave 2-(4-methoxybenzoyl)indole-3-carboxylic acid as the sole product. However, 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with anisole afforded 3-(4-methoxybenzoyl)indole-2-carboxylic acid. These carboxylic acids could be converted to the corresponding benzoylindoles.

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Paper | Regular issue | Vol 57, No. 9, 2002, pp. 1645 - 1651
Published online:
DOI: 10.3987/COM-02-9538
Synthesis of 5H-Benzo[b]carbazole-6,11-diones from Benzoylindolecarboxylic Acids

Yasuyoshi Miki,* Yasuhiko Tsuzaki, and Hana Matsukida

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan


Treatment of 1-benzyl-3-(4-methoxybenzoyl)indole-2-carboxylic acid with phosphorus pentachloride gave the corresponding acid chloride, which was treated with titanium(IV) chloride to afford 9-methoxy-5H-benzo[b]carbazole-6,11-dione. In a similar manner, 1-benzenesulfonyl-2-(4-methoxybenzoyl)indole-3-carboxylic acid provided 9-methoxy-5H-benzo[b]carbazole-6,11-dione. However, 1-benzyl-3-(4-methoxybenzyl)indole-2-carboxylic acid could be converted to 8-methoxy-5H-benzo[b]carbazole-6,11-dione.

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Note | Regular issue | Vol 57, No. 9, 2002, pp. 1653 - 1658
Published online:
DOI: 10.3987/COM-02-9518
Amides from the Seeds of Piper nigrum Linn. and Their Insecticidal Activity

Bina S. Siddiqui,* Tahsin Gulzar, and Sabira Begum

*H. E. J. Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan


Two new amides pipertipine (1) and pipercitine (2) have been isolated from the dried seeds of Piper nigrum along with eight known constituents of β-sitosterol, (2E, 4E, 8Z)-N-isobutyleicosatrienamide, pellitorine, guineensine, piperine, piperettine, pipericine, and (3,4-methylenedioxyphenyl)cinnamaldehyde. The structures of 1 and 2 have been elucidated as 1-[8-(3′, 4′-methylenedioxyphenyl)-(7E)-octaenoyl]piperidine and 1-[(2E)-octadecenoyl]piperidine, through extensive spectral studies including 2D NMR. New compounds 1 and 2 and most of the known exhibited toxicity against fourth- instar larvae of Aedes aegypti.

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Note | Regular issue | Vol 57, No. 9, 2002, pp. 1659 - 1682
Published online:
DOI: 10.3987/COM-02-9522
Syntheses of 3-Aminoquinoline-2,4(1H,3H)-diones

Stanislav Kafka, Antonín Klásek,* Jirí Polis, and Janez Kosmrlj

*Faculty of Technology, Tomas Bata University in Zlín, 762 72 Zlín, Czech Republic


Reaction of 3-chloro- (2) and 3-bromoquinoline-2,4(1H,3H)-diones (3) with excess of primary alkyl- or arylamines in dimethylformamide provides the corresponding 3-alkyl- or 3-arylamino derivatives (4). Compounds (4) with the primary amino group at the 3 position were best prepared by reaction of 2 with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines (4) via reduction of 3-azidoquinoline-2,4(1H,3H)-diones (5) was investigated. The reduction of 5 with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphine afforded exclusively 4-hydroxyquinolin-2(1H)-one (1).

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Note | Regular issue | Vol 57, No. 9, 2002, pp. 1683 - 1688
Published online:
DOI: 10.3987/COM-02-9523
Convenient Preparation of Tacrine Derivatives by the Reduction of 9-Aminoacridines with Nickel-aluminum Alloy

Kichinosuke Kamata,* Yoh-ichi Tominaga, Akiyoshi Tori-i, Thies Thiemann, Kazufumi Takahashi, and Shuntaro Mataka*

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


9-Amino-1,2,3,4-tetrahydro- and 9-amino-1,2,3,4,5,6,7,8-octahydro-acridine derivatives (2 and 3) were conveniently prepared in the reduction of the corresponding 2-substituted 9-aminoacridines (1a-f) with nickel-aluminum alloy under basic conditions. The reduction is dependent upon the nature of the substituent in the 2-position of the starting 9-aminoacridines.

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Note | Regular issue | Vol 57, No. 9, 2002, pp. 1689 - 1695
Published online:
DOI: 10.3987/COM-02-9535
A Convenient Synthesis of Highly Conjugated 5-Nitroimidazoles

Kamel Benakli, Thierry Terme, José Maldonado, and Patrice Vanelle*

*Laboratoire de Chimie Organique, Faculté de Pharmacie, Université de la Méditerranée, 27, Boulevard Jean Moulin, 13385 Marseille Cedex 05, France


A new series of highly conjugated 5-nitroimidazoles was prepared using electron transfer methodology in multi-steps synthesis from 2-chloromethyl-1-methyl-5-nitro-1H-imidazole.

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Note | Regular issue | Vol 57, No. 9, 2002, pp. 1697 - 1704
Published online:
DOI: 10.3987/COM-02-9540
Unexpected Formation of Pyrrolo[2,1-b]thiazoles by Rearrangement of α-Hydroxydihydro-1,4-thiazines

Hoh-Gyu Hahn,* Kee Dal Nam, and Heduck Mah

*Organic Chemistry Laboratory, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 136-791, Korea


A new synthesis of pyrrolo[2,1-b]thiazoles (5) is described. Hydrolysis of acetoxy dihydro-1,4-thiazine (2) prepared by Pummerer reaction of dihydro-1,4-thiazine sulfoxide gave the intermediate α-hydroxy sulfide (4). Dehydration of 4 gave pyrrolo[2,1-b]thiazoles (5). The reaction mechanism for the formation of 5 including the intermediate thiol (6) is discussed.

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Review | Regular issue | Vol 57, No. 9, 2002, pp. 1705 - 1715
Published online:
DOI: 10.3987/REV-02-553
The Heterocyclic Natural Products of Gorgonian Corals of Genus Briareum Exclusive of Briarane-type Diterpenoids

Ping-Jyun Sung* and Ming-Chyuan Chen

*National Museum of Marine Biology and Aquarium, 2 Houwan Road, Checheng, Pingtung, Taiwan 944, Taiwan, R.O.C.


An overview on the heterocyclic natural products of gorgonian octocorals of genus Briareum is presented. Based on previous studies, most of the heterocyclic natural products from Briareum are diterpenoid metabolites, including eunicellin, asbestinane, cembrane, and briarane-type derivatives. The structures, names, biological activities, and references of these natural products exclusive of briaranes are described in this review.

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Review | Regular issue | Vol 57, No. 9, 2002, pp. 1717 - 1740
Published online:
DOI: 10.3987/REV-02-554
1,3-Dihydro-2,1-benzisothiazole 2,2-Dioxides (Benzosultams) in Organic Synthesis

Krzysztof Wojciechowski

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


Methods of synthesis of 1,3-dihydro-2,1-benzisothiazole 2,2-dioxides and their applications in the synthesis of heterocyclic compounds are reviewed.

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14 data found. 1 - 14 listed