Regular Issue

Vol. 51, No. 8, 1999

23 data found. 1 - 23 listed
Communication | Regular issue | Vol 51, No. 8, 1999, pp. 1775 - 1778
Published online:
DOI: 10.3987/COM-99-8569
Photoreactions of N-Tosyldihydrodiazaazulanones to Form Diazaazulaones and Ionic Pairs between p-Toluenesulfonate Anion and Tropylium Ions

Tadayuki Doi, Hiroyuki Ishiguro, Michie Sato, and Katsuhiro Saito*

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Low pressure mercury lamp irradiations of N-aryl-N’-tosyldthydrodiazaazulanones in acetonitrile afforded the corresponding N-aryldiazaazulanones. Analogous photoreactions but using tetrahydrofuran as a solvent gave ion pairs between p-toluenesulfonate (tosylate) anion and the corresponding tropylium ions. The reactions are conisidered to proceed via bond cleavage between the nitrogen atoms and the tosyl groups to form ionic intermediates, which leave tosylate anions and protons to form the diazaazulanone derivatives or give the ion pairs via hydrogen transfers.

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Communication | Regular issue | Vol 51, No. 8, 1999, pp. 1779 - 1783
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DOI: 10.3987/COM-99-8597
Photostimulated Reductive Cyclization of o-Nitrophenylazo Dyes Using Sodium Hydroxide in Isopropyl Alcohol. A New Synthesis of 2-Aryl-2H-benzotriazoles

Woonphil Baik,* Chang Hyun Yoo, Sangho Koo, Hern Kim, Yong Hyun Hwang, Byeong Hyo Kim, and Seok Woo Lee

*Department of Chemistry, Myong Ji University, Yong In, Kyung Ki-Do, 449-728, Korea


o-Nitrophenylazo dyes with NaOH were irradiated in isopropyl alcohol to give the corresponding benzotriazoles. The photostimulated reductive cyclization proceeds through the formation of N-oxides as an intermediate.

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Communication | Regular issue | Vol 51, No. 8, 1999, pp. 1785 - 1788
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DOI: 10.3987/COM-99-8605
Novel One-Pot Preparation of 5-Methoxylated Indoline and Indole Derivatives Using a Hypervalent Iodine(III) Reagent

Hirofumi Tohma, Hiroaki Watanabe, Shinobu Takizawa, Tomohiro Maegawa, and Yasuyuki Kita*

*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


A novel and efficient one-pot preparation of 1-tosylindoline and indole derivatives from N-tosylaniline derivatives (1) and activated olefin derivatives (2) using a hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), is described.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1789 - 1805
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DOI: 10.3987/COM-99-8505
Synthesis of the g-Sulfinic Acid and g-Nitro Analogues of 5-Deazatetrahydrofolic Acid

Ronald A. Forsch, Joel E. Wright, and Andre Rosowsky*

*Dana-Farber Cancer Institute, Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 44 Binney Street, Boston, Massachusetts 02115, U. S. A.


Analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid with a γ-sulfinic acid group or γ-nitro group in place of the γ-carboxyl group of the glutamate side chain were synthesized as diastereomeric mixtures, and were tested for their ability to in-hibit the growth of CCRF-CEM human leukemia cells in culture. The concentration of the γ-sulfinic acid analogue (7) giving 50% inhibition of growth during 120 h of continuous drug treatment was 21 μM versus 93 μM for the γ-nitro analogue (8). The Ki of 7 as a competitive inhibitor of the influx of [3H]methotrexate into CCRF-CEM cells via the reduced folate carrier (RFC) was 5.0 μM, a value close to the Km values typically cited in the literature for MTX and natural reduced folates. Thus, apart from any other mechanistic targets this compound might have, 7 has the potential to deplete endogenous pools of reduced folates in dividing cells by interfering with RFC function.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1807 - 1817
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DOI: 10.3987/COM-99-8518
Synthesis of Carbohydrate-derived 1,2,3-Triazoles Using 1,3-Dipolar Cycloaddition on a Soluble Polymer Support

Scott Freeze and Peter Norris*

*Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, OH 44555-3663, U.S.A.


1,3-Dipolar cycloaddition reactions of a soluble polymer-linked D-xylofuranose-derived azide (5) with acetylenes have been studied. The utility of the method for the synthesis of reversed-nucleoside triazole analogs is demonstrated.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1819 - 1826
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DOI: 10.3987/COM-99-8545
Gould-Jacob Type of Reaction in the Synthesis of Thieno[3,2-e]pyrimido[1,2-c]pyrimidines: A Comparison of Classical Heating vs Solvent-Free Microwave Irradiation

Chaitanya G. Dave* and Rina D. Shah

*Organic Synthesis Laboratory, M. G. Science Institute, P. O. Box 4007, Navrangpura, Ahmedabad 300 009, India


Gould-Jacob type of reaction for the synthesis of thieno[3,2-e]pynmido[1,2-c]pyrimidines (5) has been carried out conventionally by the condensation between 4-aminothieno[2,3-d]pyrimidines (2) and diethyl ethoxymethylenemalonate (3) via acyclic intermediates diethyl N-[5,6-disubstituted thieno[2,3-d]pyrimidin-4-yl]aminomethylenemalonates (4) and the results obtained were compared with single step microwave technique under solvent free conditions for the synthesis of 5.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1827 - 1842
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DOI: 10.3987/COM-99-8550
General Strategies in the Preparation of Antirhine-Type Indole Alkaloids

Pirjo Hanhinen, Tiina Putkonen, and Mauri Lounasmaa*

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland


Preparation of dimethyl malonyl-substituted indolo[2,3-a]quinolizidine derivative (9), which is a potential synthon in the antirhine (1) series, has been studied. Routes passing through intermediates (22) or (26) are superior to the route passing via intermediate (7), earlier preconized for that purpose.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1843 - 1848
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DOI: 10.3987/COM-99-8551
Cyphoplectine, a Norditerpene Alkaloid from Delphinium cyphoplectrum

Ali H. Meriçli,* Filiz Meriçli, C. Vildan Seyhan, Hasan Özçelik, Neset Kilinçer, A. Güray Ferizli, and Ayhan Ulubelen*

*Faculty of Pharmacy, University of Istanbul, 34452 Istanbul, Turkey


From the aerial Parts of Delphinium cyphoplectrum Boiss., a new norditerpene alkaloid named cyphoplectine has been isolated along with the known norditerpene alkaloids browniine and delphatine. The structure of cyphoplectine was established on the basis of 1H, 13C, APT, homonuclear 1H COSY, HETCOR and NOESY NMR studies. The alkaloidal mixture showed slight antifeedant and insect repellent activities.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1849 - 1854
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DOI: 10.3987/COM-99-8560
Synthesis and Structure of Norbornane/ene-fused Thiouracils and Thiazino[3,2-a]pyrimidinones

Géza Stájer,* Angela E. Szabó, and Pál Sohár

*Institute of Pharmaceutical Chemistry, albert szent-györgyi Medical University,POB 121, H-6701 Szeged, Eötvös u. 6, Hungary


Ethyl diexo-3-aminobicyclo[2.2.1]heptane- and -hept-5-ene-2-carboxy-lates (1a,b) and the diendo derivatives were transformed with thiophosgene to the isothiocyanates (2a,b and 3a,b) and then cyclized to the norbornane/ene-condensed 2-thioxopyrimidin-4-ones (4a,b and 5a,b). On heating, the norbornene compounds (4b and 5b) furnished thiouracil (6) via cyclopentadiene elimination. With dimethyl acetylenedicarboxylate, the thioxopyrimidinones (4a,b) and (5a,b) form angularly-fused [1,3]thiazino[3,2-a]pyrimidinones (7a,b and 8a,b). On heating, 7b decomposes to give 3-methyl-2,3-dihydro-2-thioxo-4(1H)-pyrimidi-none (9) in a retro Diels-Alder process by methyl migration and splitting-off of cyclopentadiene. The structures were elucidated by IR and NMR spectroscopies, with DNOE, DEPT and 2D-HSC techniques.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1855 - 1868
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DOI: 10.3987/COM-99-8561
Ring Closure of 4-Substituted 1-Amino-1-(2-aminoanilino)-2,4-dicyanobuta-1,3-diene via 5-exo-Trig and 6-exo-Dig Process

Yoshimi Yamaguchi, Kaname Takagi, Yoshihisa Okamoto*, Kazuho Harada, and Yoshihisa Kurasawa

*Center for Natural Sciences, Kitasato University, 1-15-1, Kitasato, Sagamihara, Kanagawa 228-8555, Japan


Reaction conditions for ring closures of 4-substituted 1-amino-1-(2-aminoanilino)-2,4-dicyanobuta-1,3-diene(1) were described in the light of Baldwin’s rule. A new route to 6-alkoxy-3-(2-benz-imidazolinylidene)-5-cyano-2-imino-2,3-dihydropyridine(9) was also developed from 1,5-dinitrile(1).

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1869 - 1875
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DOI: 10.3987/COM-99-8564
Synthesis and Antimalarial Activity of dl-Deoxyfebrifugine

Yasuo Takeuchi,* Shin-ichiro Tokuda, Tomoko Takagi, Midori Koike, Hitoshi Abe, Takashi Harayama, Yasuharu Shibata, Hye-sook Kim, and Yusuke Wataya

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


dl-Deoxyfebrifugine (3) was synthesized from 2-piperidone (4) by two methods via the Wittig reaction of 2-hydroxypiperidine (6). The antimalarial activity of 3 was discussed.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1877 - 1882
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DOI: 10.3987/COM-99-8589
Direct Synthesis of α-(Benzotriazol-1-yl)alkyl Ethers

Alan R. Katritzky,* Michael V. Voronkov, Alfredo Pastor, and Douglas Tatham

*Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, U.S.A.


α-(Benzotriazol-1-yl)alkyl ethers were prepared in synthetically useful yields by direct reaction of the corresponding ethers with N-chlorobenzotriazole in the presence of Lewis acids.

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Paper | Regular issue | Vol 51, No. 8, 1999, pp. 1883 - 1889
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DOI: 10.3987/COM-99-8595
Two New Quinazoline-Quinoline Alkaloids from Peganum nigellastrum

Zhong-Ze Ma, Yoshio Hano, Taro Nomura,* and Ying-Jie Chen

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Two new quinazoline-quinoline alkaloids, luotonins E (1) and F (2), were isolated from the aerial parts of Peganum nigellastrum along with two known alkaloids 3-quinolinecarboxamide (3) and pegamine (4). The structures of luotonins E and F were determined to be the formulae (1) and (2), respectively, by spectroscopic and synthetic methods.

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1891 - 1896
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DOI: 10.3987/COM-99-8537
Synthesis of Reactive s-Triazines Bearing a Cage System Derived from Adamantane as Precursors of Hexamethylmelamine Analogues

Mir Hedayatullah,* Claude Lion, Amel Ben Slimane, Louis Da Conceiçao, and Imad Nachawati

*Institut de Topologie et de Dynamique des Systémes, associe au CNRS, UPRES-A 7086, Université de Paris 7 - Denis Diderot , 1, rue Guy de la Brosse, 75005 Paris, France


The synthesis of reactive s-triazines from cyanuric chloride and 1-adamantanamine, 1-adamantanol, 2-adamantanol, 1-adamantanemethanol and their use in the preparation of structural analogues of hexamethylmelamine are described.

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1897 - 1903
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DOI: 10.3987/COM-99-8541
Delbruninol, a New Norditerpenoid Alkaloid from Delphinium brunonianum Royle

Ahyan Ulubelen, Haridutt K. Desai, Quincy Teng, Ali H. Meriçli, Filiz Meriçli, Ufuk(Sönmez) Kolak, Muhammad Arfan, Chung K. Lee, and S. William Pelletier*

*Department of Chemistry, Institute for Natural Products Research, The University of Georgia, Chemistry Building, Athens, Georgia 30602-2556, U.S.A.


A new norditerpenoid alkaloid, delbruninol (1), has been isolated from the aerial parts of Delphinium brunonianum Royle Its structure has been established on the basis of its spectroscopic data (IR, HRFABMS, 1H, 13C,1H-1H and 1H-13C COSY, ROESY, TOCSY, HMQC-TOCSY and HMBC NMR spectra). The known alkaloids delcosine, browniine, blacknidine, delbrunine, 18-methoxygadesine and nudicaulamine were also isolated and identified. The roots of D. brunonianum Royle furnished the known alkaloids methyllycaconitine and lycoctonine.

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1905 - 1912
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DOI: 10.3987/COM-99-8546
Demethylation-Sulfonation of 2',3',4'-Trimethoxyflavones

Amar Habsaoui,* José Luis Franquet Cami, Emile M. Gaydou, and Jean-Claude Wallet

*Laboratorie de Phytochimie, Case 412, Faculté del Sciences de St-Jérome, Avenue Escadrille Normandie-Niemen 13397 Marseille Cedex 20, France


Total demethylation of 2í,3í,4í-trimethoxyflavones with sulfuric acid was realised at mild temperature giving respective 2í,3í,4í-trihydroxyflavone-5í-sulfonic acids. A multi steps mechanism is proposed in the light of earlier results and the complete assignment of the ëH and ë3C NIVIIR spectra of a suggested 3í-hydroxy-2í,4í-dimethoxy intermediate.

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1913 - 1919
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DOI: 10.3987/COM-99-8565
Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Ethyl Nipecotate-derived New Chiral Ligand

So Ha Lee, Dai Sig Im, Chan Seong Cheong,* and Bong Young Chung

*Medicinal Chemistry Research center, Life Science Division, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 131-650, Korea


(R)-(-)-Diphenyl-(N-methylpiperidin-3-yl)methanol (3) derived from (±)-ethyl nipecotate catalyzed the enantioselective addition of diethyizinc to various aldehydes in good to moderate optical yield (40 % - 81 %).

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1921 - 1928
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DOI: 10.3987/COM-99-8566
Reductive Reactions of Nitroarenes in the Presence of Allyl Bromide and Zinc Dust

Byeong Hyo Kim,* Tae Kyu Kim, Jae Wook Cheong, Sang Woo Lee, Young Moo Jun, Woonphil Baik, and Byung Min Lee

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


Under the mild condition, allyl bromide/Zn mediated reductive N,O-diallylation of nitrobenzene was observed. In case of o-nitroarenes such as 2-nitrobenzaldehyde derivatives, 2’-nitroacetophenone, and N-(2-nitrobenzylidene)anilines, reductive cyclizations were accomplished in good to excellent yields. Synthesis and mechanistic details are discussed.

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1929 - 1943
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DOI: 10.3987/COM-99-8572
Synthesis of N-(4,6-Dimethylpyridin-2-yl)benzoxazolinonyl Methylcarboxamides with Potential Antiinflammatory Activity

Messaoud Liacha, Saïd Yous, Patrick Depreux,* Jacques H. Poupaert, and Daniel Lesieur

*Institut de Chimie Pharmaceutique, Albert Lespagnol, Université de Lille 2 - Droit et Sante, 3, rue du Professeur Laguesse, BP 83, 59006 Lille Cedex, France


New aryl(alkyl)carboxamides issued from 2-amino-4,6-dimethylpyridine and benzoxazolinone pharmacophores designed as antiinflammatory agents were synthesized from suitable methyl substituted o-aminophenols.

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1945 - 1948
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DOI: 10.3987/COM-99-8600
Selective Electrocatalytic Oxidation of Primary and Secondary Alcohols Mediated by Decahydroquinolinyl-N-oxyl Radical

Yoshitomo Kashiwagi,* Futoshi Kurashima, Jun-ichi Anzai, and Tetsuo Osa

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, sendai 980-8578, Japan


(±)-cis,cis4-Benzoyloxy-2,2,8a-trimethyldecahydroquinolinyl-N-oxyl reveals a reversible redox peak whose oxidation potential is at + 0.67 V vs. Ag/AgCl. The compound catalyzed the selective oxidation reactions of primary and secondry alcohols to aldehydes and ketones, respectively, in high current efficiency (86.4-92.7 %) and selectivity (100 %).

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Note | Regular issue | Vol 51, No. 8, 1999, pp. 1949 - 1956
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DOI: 10.3987/COM-99-8608
Nucleophilic Substitution Reaction of 3-Acetyl-1-methoxyindole and Its Application for the Synthesis of Novel 2-Substituted Methyl 2,3-Dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates

Masanori Somei,* Masahiro Nakajou, Tsuyoshi Teramoto, Asuka Tanimoto, and Fumio Yamada

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


A simple synthetic route was established for 3-acetyl-1-methoxyindole, which was found to undergo nucleophilic substitution reactions selectively at the 2-position. Applying the reaction, novel 2-substituted methyl 2,3-dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates were prepared.

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Review | Regular issue | Vol 51, No. 8, 1999, pp. 1957 - 1970
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DOI: 10.3987/REV-99-518
Synthesis of Heterocycles Using the Intramolecular Heck Reaction Involving a 'Foraml' Anti-elimination Process

Masazumi Ikeda,* Serry A. A. El Bialy, and Takayuki Yakura

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyorto 607-8414, Japan


This review summarizes the synthetic studies of a variety of heterocycles using the intramolecular Heck reaction which involves a formal anti-elimination of HPdX.

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Review | Regular issue | Vol 51, No. 8, 1999, pp. 1971 - 2000
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DOI: 10.3987/REV-99-521
Nx-Oxygenated Adenines: Their Chemistry, Physicochemical Properties, and Biological Activities

Tozo Fujii* and Taisuke Itaya

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


6-Hydroxyaminopurine (2), 6-nitrosopurine (3), 6-nitropurine (4), adenine 1-oxide (5), adenine 3-oxide (6), adenine 7-oxide (7), and 9-hydroxyadenine (8) may be accepted as members of the Nx-oxygenated adenine family. The chemistry, physicochemical properties, and biological activities of these Nx-oxygenated adenines are reviewed with 214 reference citations.

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23 data found. 1 - 23 listed