Regular Issue

Vol. 63, No. 8, 2004

16 data found. 1 - 16 listed
Communication | Regular issue | Vol 63, No. 8, 2004, pp. 1757 - 1763
Published online: 1st June, 2004
DOI: 10.3987/COM-04-10097
A New Method for Regioselective Synthesis of a Broad-Spectrum Parenteral S-3578-Related Cephalosporin Bearing an Imidazo[4,5-b]pyridinium Derivative at C-3

Hidenori Yoshizawa, Katsuki Yokoo, Takashi Nomura, Takafumi Ohara, Koji Ishikura,* and Yasuhiro Nishitani

*Shionogi Rresearch Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan


A broad-spectrum S-3578-related cephalosporin, 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-fluoromethoxyiminoacetamido]-3-[1-(3-methylamino-propyl)-1H-imidazo[4,5-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate sulfate was regioselectively synthesized in a good yield using diaminopyridine derivative bearing a dimethylformamidine group.

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Communication | Regular issue | Vol 63, No. 8, 2004, pp. 1765 - 1770
Published online: 6th July, 2004
DOI: 10.3987/COM-04-10138
Synthesis of 5-Methylindole-4,7-quinone through a New Construction of the Functionalized Indole Ring Based on the Allene-mediated Electrocyclic Reaction Involving the Pyrrole [b]-Bond

Maho Hirayama, Tominari Choshi, Teppei Kumemura, Shigeo Tohyama, Junko Nobuhiro, and Satoshi Hibino*

*Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan


A new synthesis of an indole ring based on an electrocyclic reaction of a 2-alkenyl-3-allenylpyrrole intermediate generating from 2-ethenyl-3-propargylpyrrole was established. A synthesis of 5-methylindole-4,7-quinone (1) was completed in seven steps from the 4-oxygenated 5-methylindole (13a). It was demonstrated that the structure of natural product (1), isolated from Dropella fragum, is not at least 5-methylindole-4,7-quinone (1).

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1771 - 1781
Published online: 4th June, 2004
DOI: 10.3987/COM-04-10074
Synthesis of Benzofurans from Isovanillin via C-Propenylation-O-Vinylation and Ring-closing Metathesis

Tzu-Wei Tsai, Eng-Chi Wang,* Keng-Shiang Huang, Sie-Rong Li, You-Feng Wang, Yu-Li Lin, and Yung-Hua Chen

*Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung City 807, Taiwan, R.O.C.


Substituted benzofurans derived from isovanillin were synthesized. 2-Allyl-3-alkoxy-4-methoxyphenol, prepared from isovanillin via the Claisen rearrangement, O-alkylation and Baeyer-Villiger oxidation, were chloroethylated by two-phase reaction to furnish 1-allyl-3-alkoxy-(2-chloroethoxy)-4-methoxybenzenes. The given compounds were treated with potassium tert-butoxide to undergo the isomerization of O-allyl group and dehydrochlorination of 2-chloroethoxy group to efficiently construct the precursors with C-propenyl- O-vinyl function for the ring-closing metathesis (RCM) in one pot. Then, then precursors were subjected to RCM to furnish 4,5-O-difunctionalized benzofurans in good over-all yield, respectively.

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1783 - 1792
Published online: 9th July, 2004
DOI: 10.3987/COM-04-10084
Condensation of 4-Hydroxy-2-thiazolines with 1,2-Phenylenediamine as a Novel Effective Route to Thiazolo[3,4-a]quinoxalines

Vakhid A. Mamedov,* Ilsiyar Z. Nurkhametova, Aidar T. Gubaidullin, Igor A. Litvinov, and Sadao Tsuboi*

*Department of Environmental Chemistry and Materials, Faculty of Environmental Science and Technology, Okayama University, 2-1-1 Tsushima-naka, Okayama 700-8530, Japan


Thiazolo[3,4-a]quinoxalin-4-ones were prepared in two steps starting from methyl phenylchloropyruvate using a new strategy for the construction of the ring system. A key step in this new method involves the reaction of 4-hydroxytetrahydrothiazoles with 1,2-phenylendiamines.

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1793 - 1812
Published online: 25th June, 2004
DOI: 10.3987/COM-04-10089
Synthesis of Hydroxyquinoline Derivatives, Aminohydroxychromene, Aminocoumarin and Their Antibacterial Activities

Alaa S. Abd-El-Aziz,* Ahmed M. El-Agrody, Ahmed H. Bedair, T. Christopher Corkery, and Athar Ata

*Department of Chemistry, The University of Winnipeg, Winnipeg, Manitoba, R3B 2E9, Canada


Some new diaminochromenes (3a-f, 7a-c, and 10), 7-amino-4-aryl-coumarins (8a,b), 7-hydroxy-4-aryl-1,2-dihydroquinolines (9a-c) and 2-amino-7-hydroxy-4-(4-chlorophenyl)-4H-chromenes (16a-d) were synthesized via Michael addition of different substituted aminonaphthol (1), aminophenol (6), resorcinol derivatives (15a-d), chloronaphthol (17) and 4-hydroxycoumarin (19) with α-cyanocinnamonitriles (2a-c) and ethyl α-cyanocinnamate (2d-f). 2-Acetylamino-7-amino-4-(4-chlorophenyl)-4H-chromene-2-carbonitrile (14) was obtained as a unique product via hydrazinolysis of ethoxymethyleneamino derivative (13). The formation of coumarins (8a,b) and quinolines (9a-c) were anomalous case. Structures of the titled compounds cited in this article were elucidated by spectrometric data (IR, 1H NMR, 13C NMR (APT) and EMS). All of the newly synthesized compounds were evaluated for antimicrobial activities, where 16b and 16c exhibited activity against staphylococcus aureus (ATCC 25923).

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1813 - 1819
Published online: 8th June, 2004
DOI: 10.3987/COM-04-10099
Novel Synthesis of 3-Substituted Derivatives of (Alkyliden-1-yl)-3H-benzo[b]thiophen-2-ones

Sukanta Kamila and Edward R. Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275-0314, U.S.A.


The reaction of 2-methylthiophenol with sodium hydride and N,N-diethylcarbamyl chloride in THF afforded N,N-diethylthiocarbamic acid S-o-tolyl ester in 97% yield. The ester was subsequently treated with LDA and various aromatic aldehydes to provide new 3-substituted derivatives of (alkyliden-1-yl)-3H-benzo[b]thiophen-2-ones. The Z isomer was formed as major product with smaller amounts of the E isomer. The structure of (Z)-3-(thiophen-2-yl)methylidenyl-3H-benzo[b]thiophen-2-one was confirmed by X-Ray crystallography.

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1821 - 1828
Published online: 1st June, 2004
DOI: 10.3987/COM-04-10100
New Resveratrol Dimer Glucosides and Trimers in Stem and Root of Welwitschia mirabilis

Hiroko Murata, Toshiyuki Tanaka,* Ibrahim Iliya, Miyuki Furasawa, Tetsuro Ito, Ken-ichi Nakaya, and Munekazu Iinuma

*Gifu Prefectrual Institute of Health and Environmental Sciences, 1-1 Nakafudogaoka, Kakamigahara, Gifu 504-0838, Japan


Two new resveratrol dimer glucosides, mirabilosides A (1) and B (2), and two new resveratrol trimers, mirabilols A (3) and B (4) were isolated from stem and root of Welwitschia mirabilis (Welwitschiaceae) together with four known stilbene oligomers (gnetins C, E, F and I). The structures of isolated compounds were determined by spectroscopic analysis.

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1829 - 1838
Published online: 11th June, 2004
DOI: 10.3987/COM-04-10108
Synthesis of Functionalized 1H-Pyrazolo[4,3-e][1,2,4]triazines and Their Fused Derivatives via Ipso-Substitution of Methylsulfonyl Group with O-, N-, S- and C-Nucleophiles

Mariusz Mojzych and Andrzej Rykowski *

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


Ipso-substitution reaction of 3-methyl-5-methylsulfonyl-1-phenyl-1H-pyrazolo[4,3-e][1,2,4]triazine (4) with a range of C-, N-, O- and S-nucleophiles afforded the corresponding substitution products (5a-m) in high yields. The reaction of 5-hydrazino compound (5m) with carboxylic acids furnished 1H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-b][1,2,4]triazines (8a) and (8b).

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1839 - 1847
Published online: 18th June, 2004
DOI: 10.3987/COM-04-10116
SnCl4-Promoted Ethenylation Reaction of Hydroxylated Heteroarenes

Kensuke Akamatsu, Ryo Amemiya, and Masahiko Yamaguchi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan


Reaction of hydroxylated heteroarenes and acetylene in the presence of SnCl4 and Bu3N (or Et3N) gives the corresponding ethenylated arenes. The reaction takes place at the neighboring position of the hydroxy group, and is applicable to quinolines, an isoquinoline, pyridines, and N-trifluoromethanesulfonylated indoles provided that the optimized conditions for the ethenylation and workup are employed.

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1849 - 1854
Published online: 21st June, 2004
DOI: 10.3987/COM-04-10126
Synthesis of Minosamycin and 5,8-Dihydroxy-4,7-dimethloxy-2,6-dimethylisoquinolinium Iodide

Shinsuke Nakahara* and Akinori Kubo

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


The one-pot synthesis of mimosamycin utilizing the Polonovski reaction and a five-step synthesis of 5,8-dihydroxy-4,7-dimethoxy-2,6-dimethylisoquinolinium iodide (7) from known compound (8) are described.

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Paper | Regular issue | Vol 63, No. 8, 2004, pp. 1855 - 1873
Published online: 9th July, 2004
DOI: 10.3987/COM-04-10134
Allylic Dehydration, Retro-Pinacol, Pinacol-like and Enamide Reactions: Synthesis of New Isoquinolines

Rufine Akué-Gédu, Anne Bourry, Fabrice Camus, Bernadette Norberg, François Durant, Daniel Couturier, Marc DeBacker, and Benoît Rigo*

*Group de Recherche sur l’Inhibition de la Prolifération Cellulaire (EA 2692), Hautes Etudes d’Ingénieurs, 13 rue de Toul, 59046 Lille, France


Depending upon the conditions, heating of 1,10a-dihydro-2H,5H-pyrrolo[1,2-b]isoquinoline-3,10-diones in polyphosphoric or hydrochloric acid gives rise to hydride transfer and oxidative processes. Mono or dienyl lactams, or mixtures of dimers and acids or hydroxyacids of the isoquinoline series were thus formed. Procedures leading specifically to each of these products have been found.

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Note | Regular issue | Vol 63, No. 8, 2004, pp. 1875 - 1881
Published online: 18th June, 2004
DOI: 10.3987/COM-04-10067
Iridoid Galactosides and a Benzofuran Type Sesquiterpene from Buddleja crispa

Ijaz Ahmad, Nighat Afza, Itrat Anis, Abdul Malik,* Itrat Fatima, Azhar-ul-Haq, and Rasool Bakhsh Tareen

*International Centre for Chemical Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan


Buddlejosides A (1) and B (2), new iridoid galactosides, and buddlejone (3), a benzofuran type sesquiterpene, have been isolated from the EtOAc fraction of Buddleja crispa together with β-sitosterol (4) and ursolic acid (5). Their structures have been assigned on the basis of spectral analyses including 1D and 2D NMR spectral techniques.

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Note | Regular issue | Vol 63, No. 8, 2004, pp. 1883 - 1890
Published online: 11th June, 2004
DOI: 10.3987/COM-04-10092
Synthesis of Novel 5H-Pyrazolo[4,3-c]quinolines

Olexiy V. Silin, Timur I. Savchenko, Sergiy M. Kovalenko, Viktor M. Nikitchenko, and Alexandre V. Ivachtchenko*

*Chemical Diversity Labs, Inc., Sorrento Valley Rd., Suite 5, San Diego, California 11558, U.S.A.


A convenient synthesis of 3-aryl-5H-pyrazolo[4,3-c]quinolines is described. The key reactions include alkylation of 3-aroyl-1H-quinolin-4-ones with alkyl halides in DMF in the presence of sodium hydride, followed by hydrazine-mediated cyclization of the alkylated products in acetic acid.

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Note | Regular issue | Vol 63, No. 8, 2004, pp. 1891 - 1896
Published online: 1st June, 2004
DOI: 10.3987/COM-04-10110
Two New Sesquiterpene Pyridine Alkaloids from Maytenus chuchuhuasca

Osamu Shirota,* Setsuko Sekita, Motoyoshi Satake, Hiroshi Morita, Koichi Takeya, and Hideji Itokawa

*Laboratory of Pharmacognosy and Natural Product Chemistry, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki City, Kagawa 769-2193, Japan


Two new sesquiterpene pyridine alkaloids, chuchuhuanines E-VI (1) and E-VII (2), were isolated from root barks of Maytenus chuchuhuasca Raymond-Hamet et Colas (Celastraceae). Their structures were elucidated by the analysis of spectral data.

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Note | Regular issue | Vol 63, No. 8, 2004, pp. 1897 - 1901
Published online: 25th June, 2004
DOI: 10.3987/COM-04-10114
A Convenient Method for the Preparation of Some New Derivatives of 1,3,5-Triazine under Solvent-free

Davood Azarifar,* Mohammad Ali Zolfigol, and Ali Forghaniha

*Department of Chemistry, School of Science, Bu-Ali Sina University, Hamadan 65174, Iran


Nucleophilic reactions on cyanuric chloride were carried out under solvent free conditions to give 1,3,5-s-triazine derivatives with excellent yields.

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Review | Regular issue | Vol 63, No. 8, 2004, pp. 1903 - 1958
Published online: 11th May, 2004
DOI: 10.3987/REV-04-577
Formation of Five- and Six-membered Heterocyclic Rings by Radical Cyclization

Krishna C. Majumdar,* Partha P. Mukhopadhyay, and Pradipta K. Basu

*Department of Chemistry, University of Kalyani, Kalyani 741 235, West Bengal, India


This review describes the formation of different five- and six-membered heterocyclic rings in various compounds by radical cyclization.

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16 data found. 1 - 16 listed