Regular Issue

Vol. 38, No. 5, 1994

22 data found. 1 - 22 listed
Communication | Regular issue | Vol 38, No. 5, 1994, pp. 957 - 960
Published online:
DOI: 10.3987/COM-93-6642
Synthesis and Reactions of Novel Tropono[4,5-b]oxepines

Naoki Kakusawa, Masanobu Imamura, Jyoji Kurita, and Takashi Tsuchiya*

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


Reaction of pyridazine N-oxides with 4,5-didehydrotropone resulted in the formation of the novel tropono[4,5-b]oxepines and some chemical properties of the new ring system were examined.

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Communication | Regular issue | Vol 38, No. 5, 1994, pp. 961 - 964
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DOI: 10.3987/COM-93-6657
High-Pressure Intermolecular Diels-Alder Reactions of the Novel Building Block; 4H,6H-Thieno[3,4-c]furan 5,5-Dioxide

Takayoshi Suzuki, Kan Kubomura, and Hiroaki Takayama*

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1 Suarashi, Sagamiko-machi, Tsukui-gun, Kanagawa 199-0195, Japan


At high pressure, the furansulfolene, 4H,6H-thieno[3,4-c]furan 5,5-dioxide (1), whose furan and 3-sulfolene moieties could be used as diene components in Diels-Alder reactions, reacted with the dienophiles at its furan moiety selectivity.

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Communication | Regular issue | Vol 38, No. 5, 1994, pp. 965 - 970
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DOI: 10.3987/COM-93-6668
Albiflomanthine — A Crinane Alkaloid from Haemanthus albiflos (JACQ)

Geneviève Baudouin, François Tillequin, and Michel Koch*

*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 new crinane alkaloid, albiflomanthine (1) has been isolated from Haemanthus albiflos Jacq. Its structure has been elucidated on the basis of spectral analyses. It is the first crinane alkaloid to present an oxygen substituent at C-4.

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Communication | Regular issue | Vol 38, No. 5, 1994, pp. 971 - 974
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DOI: 10.3987/COM-94-6690
(S)-6-(1-Hydroxypropyl)lumazine Derivatives from the Marine Polychaete, Odontosyllis undecimdonta

Hideo Tanino,* Hiroyuki Takakura, Hisae Kakoi, Kunisuke Okada, and Shoji Inoue

*Faculty of Pharmacy, Meijo University, 150 Yagoto, Tempaku-ku, Nagoya, Aichi 468-8503, Japan


(S)-6-(1-Hydroxypropyl)-3-methyllumazine (1) and (S)-6-(1-hydroxypropyl)-1,3-dimethyllumazine (3) were isolated from the swimming polychaete, Odontosyllis undecimdonta.

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Communication | Regular issue | Vol 38, No. 5, 1994, pp. 975 - 980
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DOI: 10.3987/COM-94-6697
Taxol Related Diterpenes from the Roots of Taxus yunnanensis

Zhang Hongjie, Yoshio Takeda,* Takashi Matsumoto, Yoshinori Minami, Kenichiro Yoshida, Xiang Wei, Mu Qing, and Sun Handong*

*Faculty of Integrated Arts and Sciences, University of Tokushima, Minamijosanjima-cho, Tokushima 770-0814, Japan


Four new taxol related diterpenes were isolated from the roots of Taxus yunnanensis together with taxol, cephalomannine, 10-deacetyltaxol, and 10-deacetylcephalomannine and their structures were elucidated by spectroscopic means.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 981 - 989
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DOI: 10.3987/COM-93-6565
Ring Transformation of Heterocycles: Part 3. A Conversion of 4-Amino-Δ2-1,2,4-oxadiazolines into 2-Arylamino-1,3,4-thiadiazoles and Oxaanalogues

Ahmad Q. Hussein,* Mustafa M. El-Abadelah, Musa Z. Nazer, and Abdel M. Awadallah

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan


4-Amino-Δ2-1,2,4-oxadiazolines (1) are transformed into the corresponding 2-arylamino-1,3,4-oxadiazoles (5) or thiadiazoles (6) via reaction with phenyl isocyanate ( or phenyl isothiocyanate), followed by brief treatment of the resulting adducts (2 and 3) with trifluoroacetic anhydride at ambient temperature. Treatment of compounds (1) with trifluoroacetic anhydride gave 2-trifluoromethyl-1,3,4-oxadiazoles (8).

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 991 - 1000
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DOI: 10.3987/COM-93-6633
Chromenes and Chromanones. Part I The Birch Reduction of Coumarins and 2H-Chromenes

Miroslaw Aniol, Przemyslaw Lusiak, and Czeslaw Wawrzenczyk*

*Institute of Fundamental Chemistry, Agricultural University , Norwida 25, 50-357 Wroclaw, Poland


The reduction of coumarin, 4-methylcoumarin, 2,2-dimethyl-2H-chromene and 2,2,4-trimethyl-2H-chromene with sodium or lithium in liquid ammonia with the presence or without donor of protons was carried out. The formation of phenolic products was observed when a limited amount of alcohol as a proton donor was present in the reaction medium. In the experiments with excess of alcohol the products with a partially reduced benzene ring were formed.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1001 - 1006
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DOI: 10.3987/COM-93-6636
A Synthesis of 2-Substituted Phenylbenzothiazoles

Yvette Mettey, Sabine Michaud, and Jean Michel Vierfond*

*Laboratoire de Chimie Organique, Faculte de Pharmacie, GREAM, BP 199, 34 rue du Jardin des Plantes, 86005 Poitiers Cedex, France


A one-pot synthesis of 2-substituted phenylbenzothiazoles is achieved when 2-aminobenzenethiol is treated with an excess of sodium hydride and aromatic nitriles in THF. This method allows to obtain substituted products (F, CF3, Cl or OCH3) in each ortho, meta and para position and plurisubstituted products.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1007 - 1014
Published online:
DOI: 10.3987/COM-93-6637
Synthesis of Deoxyazepinomycin

Peter K. Bridson

*Department of Chemistry, Memphis State University, Mimphis, TN 38152, U.S.A.


The syntheses of several new derivatives of imidazo[4,5-e][1,4]diazepin-8-one are described.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1015 - 1024
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DOI: 10.3987/COM-93-6641
Cycloaddition in Synthesis of Sulfonamide Derivatives. VI Unexpected Products from the Reaction of Dithiocarbamate with Chlorosulfonyl Isocyanate a Novel Synthetic Route to 5-Amino-1,2,4-dithiazol-3-one and N,N-Disubstituted N‘-Chlorosulfonylcarbamimidoyl Chloride

Tsuneo Iwakawa,* Tomohiro Sato, and Akira Murabayashi

*Aburahi Laboratories, Shionogi & Co. Ltd., Gotanda, Koka-cho, Koka-gun, Shiga 520-3423, Japan


Reaction of propyl N-methyl-N-phenyldithiocarbamate (1a) with chlorosulfonyl isocyanate in the presence of AlCl3 gives 5-(N-methylanilino)-1,2,4-dithiazol-3-one (2), 1-methyl-2-propylthio-4-quinazolinone (3) and N-methyl-N-phenyl-S-propylthiocarbamate (4a) in addition to 3-propylthio-4H-1,2,4-benzothiadiazine 1,1-dioxide (5). However, the same reaction conducted without AlCl3 gives 2, 4a, and (Z)-N-methyl-N-phenyl-N‘-chlorosulfonylcarbamimidoyl chloride (6). Compound (2) exhibited fungicidal and antibacterial activities.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1025 - 1032
Published online:
DOI: 10.3987/COM-93-6644
Structure and Stereochemistry of Hazuntamine, a New Bisindole Alkaloid from Hazunta modesta var. Methuenii Subvar. Methuenii

Anne-Marie Bui, Bhupesh C. Das,* Eric Guittet, and Véronique Stoven

*Institut des Chimie des Substances Naturelles, C.N.R.S., Avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France


The complete stereostructure of hazuntamine, a new bisindole alkaloid from Hazunta modesta var. methuenii subvar. methuenii, has been determined mainly by the use of different spectroscopic means.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1033 - 1040
Published online:
DOI: 10.3987/COM-93-6648
Asymmetric Synthesis of the Enantiomers of 2-Aminomethyl-4-(4-fluorobenzyl)morpholine, an Intermediate of Mosapride, a Gastroprokinetic Agent

Toshiya Morie, Shiro Kato,* Hiroshi Harada, and Jun-ichi Matsumoto

*Discovery Research Laboratories, Dainippon Pharmaceutical Co., Ltd., Enoki 33-94, Suita, Osaka 564, Japan


An efficient asymmetric synthesis of the enantiomers of 2-aminomethyl-4-(4-fluorobenzyl)morpholine (3) which has served as an intermediate of mosapride (1), a potential gastroprokinetic agent, was achieved by the conversion of enantiomeric 3-chloro-1-(4-fluorobenzylamino)-2-propanol (8) to the oxomorpholine (10) followed by reduction and amination, in approximately 35% overall yield with >98% ee. This synthetic route comprises the regioselective opening of homochiral epichlorohydrin (4) with 4-fluorobenzylamine, with retention of the configuration.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1041 - 1052
Published online:
DOI: 10.3987/COM-93-6653
The Diverse Reactivity of (Benzothiazol-2-ylthio)(benzotriazol-1yl)methane

Alan R. Katritzky,* Ion Ghiviriga, and Darren J. Cundy

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


The reaction of lithiated (benzothiazol-2-ylthio)(benzotriazol-1-yl)methane with n-propyl iodide yielded: (benzothiazol-2-yl)(benzothiazol-2-ylthio)(benzotriazol-1-yl)methane, (benzothiazol-2-yl)(benzotriazol-1-yl)(propylthio)methane and (benzotriazol-1-yl)(propylthio)methane. Reactions of 2-methylthiobenzothiazole with 1-methylbenzotriazole 2-methylbenzotriazole and (benzotriazol-1-yl)(phenylthio)methane are also described.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1053 - 1060
Published online:
DOI: 10.3987/COM-93-6655
Preparation of 6-Azaandrost-4-ene-3,7,17-trione and Some Related 3-Oxygenated 6-Azaandrostanes

Thomas G. Back,* Denise L. Baron, and Jacek W. Morzycki

*Department of Chemistry, University of Calgary, Calgary, Alberta, T2N 1N4, Canada


The Synthesis of 6-azaandrost-4-ene-3,7,17-trione and of several related 3-oxygenated 6-azaandrostanes was achieved from 3β-hydroxyandrost-5-en-17-one.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1061 - 1070
Published online:
DOI: 10.3987/COM-93-6660
Preparation and Steric Structure of Condensed-Skeleton Saturated Diphenyl-substituted Isoindolones

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

*Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, H-6701 Szeged, Eötvös u.6., Hungary


The Friedel-Crafts reaction of benzene with cis-4-cyclohexene-1,2-dicarboxylic anhydride (1) yields trans-5-phenyl-cis-2-benzoylcyclohexanecarboxylic acid (2), which gave cyclohexane-condensed pyridazinone (3) with hydrazine, and cis-4,5-tetramethylene-1,2-oxazin-8-one (4) with hydroxylamine. From 2 with ethylenediamine, the saturated imidazo[2,3-a]isoindolone (5) was prepared, while the reaction of 2 with 1,3-diaminopropane furnished a mixture of two isomeric pyrimido[2,3-a]isoindolones (6a,b) differing in the relative positions of the benzene ring and cyclohexane annelation hydrogens. From the reaction of 2 with 3-aminopropanol, the oxazino[2,3-a]isoindolone (7) was obtained. The reaction of 2 with cis-2-hydroxymethylcyclohexylamine gave the tetracyclic (8), while 2 and diendo-3-hydroxymethylbicyclo[2.2.1]hept-5-enyl-2-amine yielded the isomers (9a,b), which differ in the mutual positions of the phenyl group on the quaternary carbon and cyclohexane annelation hydrogens. 1H- and 13C-nmr spectra and DNOE and 2D-HSC measurements proved that the 5-phenyl group is cis-equatorial to the two annelated hydrogens of the cyclohexane ring.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1071 - 1076
Published online:
DOI: 10.3987/COM-93-6667
Two Novel Arylbenzofurans, Garcifuran-A and Garcifuran-B from Garcinia kola

Masatake Niwa,* Kenji Terashima, Junko Ito, and Muhd Aqil

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan


Two novel arylbenzofurans, garcifuran-A and garcifuran-B were isolated from the roots of Garcinia kola (Guttiferae) and the structures were determined by spectroscopic methods.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1077 - 1087
Published online:
DOI: 10.3987/COM-93-6670
Synthetic and Conformational Studies on 5,6-Substituted Dihydro-2-thiouracils

Antonio Lorente* and Luis María Aurrecoechea

*Departamento de Química Orgánica, Universidad de Alcalá de Henares, 28871 Alcalá de Henares (Madrid), Spain


Synthetic and conformational studies on dihydro-2-thiouracils obtained from thioureas and 2-cyano-3-phenylpropenamide or ethyl 2-cyano-3-phenylpropenoates are reported.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1089 - 1098
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DOI: 10.3987/COM-94-6674
Five New Isoprenoid-substituted Flavonoids, Kanzonols M - P and R, from Two Glycyrrhiza Species

Toshio Fukai, Junko Nishizawa, Masami Yokoyama, Liming Tantai, and Taro Nomura*

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


Three new formylated isoflavan derivatives, kanzonols M, N, and O, and a new prenylated pterocarpan derivative, kanzonol P, were isolated from Glycyrrhiza uralensis along with kanzonol Q (dihydroxanthoxyletin). A new prenylated isoflavan derivative, kanzonol R, was isolated from G. glabra. These structures were elucidated on the basis of spectrometric evidence.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1099 - 1102
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DOI: 10.3987/COM-94-6681
Dihydrobenzofuran Neolignans from Arum italicum

Marina Della Greca, Antonio Molinaro, Pietro Monaco, and Lucio Previtera*

*Dipartimento di Chimica Organica e Biologica, Università Federico II, Via Mezzocannone 16, I-80134 Napoli, Italy


A mixture of two new enantiomeric dihydrobenzofuran neolignans has been isolated from Arum italicum. Tthe structures have been determined on the basis of the physical data of the compounds.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1103 - 1118
Published online:
DOI: 10.3987/COM-94-6684
Radical Reaction of 1-(2-Bromoarylmethyl)-2-silatetralins: Formation of Polycyclic Organosilicon Compounds

Akihisa Hirokawa, Atsuhiro Tatsuno, and Osamu Hoshino*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan


Radical reaction of 1-(2-bromoarylmethyl)-2-silatetralins (4a-f) with Bu3SnH in boiling benzene containing AlBN was found to give novel tetracyclic (5a-f) and tricyclic (6a-f) organosilicon compounds, and 9-silylphenanthrenes (7a-c), respectively.

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Paper | Regular issue | Vol 38, No. 5, 1994, pp. 1119 - 1125
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DOI: 10.3987/COM-94-6685
A New Route to Antibacterial Trimethoprim

Kenichi Harada, Tominari Chosi, Eiichi Sugino, Kohichi Sato, and Satoshi Hibino*

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


3-Methylthio-2-(3‘,4‘,5‘-trimethoxybenzyl)acrylonitrile (6) derived from 3,4,5-trimethoxyphenylacetaldehyde (2) in a four step sequence was utilized as a new three carbon unit of trimethoprim (1).

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Review | Regular issue | Vol 38, No. 5, 1994, pp. 1127 - 1155
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DOI: 10.3987/REV-92-454
Enamine Rearrangement

Sergei P. Gromov* and Aleksei N. Kost

*Institute of Chemical Physics, Russian Academy of Sciences, Kosygin Street 4, Moscow 117334, Russia


The data on enamine rearrangement of heterocyclic systems containing a pyridine ring are generalized and systematized over the period of up to 1992.

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22 data found. 1 - 22 listed