HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 63, No. 8, 2004
Published online: 1st June, 2004
■ 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
Abstract
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.
Published online: 6th July, 2004
■ 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
Abstract
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).
Published online: 4th June, 2004
■ 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.
Abstract
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.
Published online: 9th July, 2004
■ 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
Abstract
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.
Published online: 25th June, 2004
■ 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
Abstract
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).
Published online: 8th June, 2004
■ 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.
Abstract
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.
Published online: 1st June, 2004
■ 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
Abstract
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.
Published online: 11th June, 2004
■ 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
Abstract
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).
Published online: 18th June, 2004
■ 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
Abstract
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.
Published online: 21st June, 2004
■ 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
Abstract
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.
Published online: 9th July, 2004
■ 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
Abstract
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.
Published online: 18th June, 2004
■ 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
Abstract
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.
Published online: 11th June, 2004
■ 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.
Abstract
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.
Published online: 1st June, 2004
■ 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
Abstract
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.
Published online: 25th June, 2004
■ 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
Abstract
Nucleophilic reactions on cyanuric chloride were carried out under solvent free conditions to give 1,3,5-s-triazine derivatives with excellent yields.
Published online: 11th May, 2004
■ 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
Abstract
This review describes the formation of different five- and six-membered heterocyclic rings in various compounds by radical cyclization.