Regular Issue

Vol. 41, No. 10, 1995

22 data found. 1 - 22 listed
Communication | Regular issue | Vol 41, No. 10, 1995, pp. 2157 - 2160
Published online:
DOI: 10.3987/COM-95-7189
Preparations of Tryptamine-4,5-dinones, and Their Diels-Alder and Nucleophilic Addition Reactions

Masanori Somei,* Yoshikazu Fukui, and Masakazu Hasegawa

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


Syntheses of Nb-acetyltryptamine-4,5-dione and (±)-Nb-acetyltryptophan-4,5-dione methyl ester are reported. They were excellent dienophiles as well as good electrophiles, and produced 6,7-disubstituted indoles in Diels-Alder reaction and various 7-substituted indoles with nucleophiles.

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Communication | Regular issue | Vol 41, No. 10, 1995, pp. 2161 - 2164
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DOI: 10.3987/COM-95-7192
Simple Synthesis of 2,2'-Bisindole from Indigo and Its Application for the Syntheses of Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)dione and -5-(6H)one Derivatives

Masanori Somei,* Hiroyuki Hayashi, Tohru Izumi, and Shinobu Ohmoto

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


Indiogo was converted to 2,2’-bisindole, from which 6-substituted indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)dione and -5-(6H)one derivatives were prepared in short steps. Bromination of 6-methylindolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)dione is also reported.

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Communication | Regular issue | Vol 41, No. 10, 1995, pp. 2165 - 2167
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DOI: 10.3987/COM-95-7199
New Dibenzofuran Formation from the Reactions of 1-Cyclohexenyloxydibutylboranes with 2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ)

Kiyoshi Tanemura,* Koji Yamaguchi, Hideo Arai, Tsuneo Suzuki, and Takaaki Horaguchi*

*School of Dentistry at Niigata, The Nippon Dental University, Hamaura-cho 1-8, Niigata 951, Japan


1-Cyclohexenyloxydibutylboranes, generated in situ, reacted with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) to give dibenzofurans.

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Communication | Regular issue | Vol 41, No. 10, 1995, pp. 2169 - 2172
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DOI: 10.3987/COM-95-7201
Synthesis and Properties of Thienyl and Oligothienyl Substituted Tropylium Ions

Takayasu Nihira, Shinji Tarutani, Kahei Takase, and Kazuko Takahashi*

*Department of Chemistry, Faculty of Science, Tohoku University, Sendai 980-77, Japan


2-Thienyl- and 2,2’-bithienyl-5-yltropylium ions, as well as 2,5-thienylenebis(tropylium), 2,2’-bithienyl-5,5’-diylbis(tropylium), and 2,2’:5’,2":5",2’’’-quaterthienyl-5,5’’’-diylbis(tropylium) ions have been synthesized and their electronic structures in the ground and excited states have been clarified.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2173 - 2179
Published online:
DOI: 10.3987/COM-95-7051
Synthesis of 5-Oxo-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine-8-carbonitriles,6-Oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrimidine-9-carbonitriles, and 7-Oxo-1,2,3,4,5,7,8,9-octahydropyrido[1,2-a][1,3]diazepine-10-carbonitriles

Pedro Victory, Núria Busquets, José I. Borrell,* Jordi Teixidó, Carlos de Alvaro, Anna Arenas, Angel Alvarez-Larena, and Joan F. Piniella

*Departament de Química Orgànica, CETS Institut Químic de Sarrià , Universitat Ramon Llull, E-08017 Barcelona, Spain


A simple method for the synthesis of the title compounds is described. Thus, α,β-unsaturated esters (1) are transformed in the already described 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles (3) which are treated with NH2(CH2)nNH2 (n = 2, 3, 4) to afford the corresponding bicyclic compounds is determined by an X-ray structure analysis of 4a. A ring opening-ring closure mechanism is proposed for the formation of structures (4 - 6) on the basis of the reaction between 3b and 15N,15N’-ethylenediamine which afforded 15N,15N’-4b.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2181 - 2188
Published online:
DOI: 10.3987/COM-95-7084
Formation of Dihydroaza-azulanones Possessing Spirocyclic Moieties: [8+2] Type Cycloaddition Reactions of Iminotropones to an Exocyclic Double Bond of 8-Oxoheptafulvene

Yuka Saito, Masayuki Tomita, Hiroshi Taniguchi, Hirofumi Okabayashi, and Katsuhiro Saito*

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


Reactions of N-(p-substituted phenyl) iminotropones with 8-oxoheptafulvene proceeded through [8+2] type cycloadditions to form dihydroaza-azulanones possessing spirocyclic and norcaradiene moieties. Reactions of 8-oxoheptafulvene with phenyl- or tosylhydrazones of tropone gave the same type of dihydroazaazulanones. Analogous reactions with N-alkyliminotropone N-oxides also gave the same type of adducts via the corresponding N-alkyliminotropones, which were derived from reactions of the iminotropone N-oxides with 8-oxoheptafulvene.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2189 - 2194
Published online:
DOI: 10.3987/COM-95-7112
Selective Beckmann Rearrangements. Preparation of Isomeric 2,6- and 3,6-Diazepinoisoquinolines and -pyridoindoles

Pál Scheiber* and Péter Nemes

*Department of Chemistry, University of Veterinary Science, H- 1400 Budapest, P.O.Box 2, Hungary


Z and E oximes (2, 3, 6, 7) of some benzoquinolizidones (1) and indoloquinolizidone were converted into isomeric diazepinoisoquinolines (4, 5) and diazepinopyridoindoles (8, 9), respectively, via Beckmann ring enlargement. The 1-isopropyl-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-one (1c) exhibits a cis "b" B/C ring junction.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2195 - 2202
Published online:
DOI: 10.3987/COM-95-7124
Studies on Azinethiones: A Novel Synthesis of Bis(azinyl) Trithiocarbonates and Multi-fused Thienoazines

Ayman W. Erian* and Sherif M. Sherif

*Department of Chemistry, Faculty of Science, University of Cairo, Giza, A. R. Egypt


A study of the reactivity of azinethione series toward carbon disulphide has been carried out which resulted in a synthesis of bis(azinyl)trithiocarbonates. Reaction of 4-methylazinethiones with N-bromosuccinimide affords in one pot reaction unexpected multifused heterocyclic compounds.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2203 - 2219
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DOI: 10.3987/COM-95-7128
6- Fluoro-7-(1-piperazinyl)quinoxaline 1,4-Dioxide. Part I. 2-(N-2-Hydroxyalkylcarbamoyl) Derivatives

Mustafa M. El- Abadelah,* Musa Z. Nazer, Naser S. El-Abadla, and Herbert Meier*

*Johannes Gutenberg-Universität Mainz, Institut für Organische Chemie, D-55099 Mainz, Germany


A series of N-[6-fluoro-7-(4-methyl-1-piperazinyl)-3-methyl-2-quinoxaloyl]-β-aminoalkanol 1,4-dioxides (12a-h) have been synthesized for bioassay via the Beirut reaction of 5(6)-fluoro-6(5)-(4-methyl-1-piperazinyl)benzofuroxan (9) with the appropriate N-acetoacetyl-β-aminoalkanol in the presence of triethylamine. Preliminary in vitro investigations have indicated that none of the title compounds exhibits any significant antibacterial potency at concentrations ≤ 200 μg / ml.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2221 - 2231
Published online:
DOI: 10.3987/COM-95-7131
Studies on Nitrogen-containing Heterocyclic Compounds. Syntheses and Reactions of Benzo[g]quinoline

Isao Takeuchi, Makoto Ushida, Yoshiki Hamada,* Tomoaki Yuzuri, Hiroko Suezawa, and Minoru Hirota

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468, Japan


The authors devised a new convinient synthesis of benzo[g]quinoline (2) through the condensation of β-naphthylamine with malondialdehyde (MDA) followed by cyclization in polyphosphoric acid. The reactivity of 2 toward N-oxidation, Reissert reaction and methylation with methylsulfinylmethyl carbanion was investigated.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2233 - 2244
Published online:
DOI: 10.3987/COM-95-7146
Synthesis and Stereochemistry of Chiral 1,3-Dioxanic Compounds Obtained from α-Alkylated β-Ketoesters

Ion Grosu* , Sorin Mager, Gérard Plé, Roberto Martinez, Luminita Muntean, and Eugen Mesaros

*Instituto de Química, Universidad Nacional Autónama de México, Ciudad Universitaria, Circuito Exterior, Mexico D.F., 04510, Mexico


1,3-Dioxanic compounds were obtained by the ketalisation reaction of some α-alkylated β-ketoesters. The conformational analysis by means of 1H- and 13C-nmr investigations showed the anancomeric structure of the compounds. The axial or the equatorial position of the groups was inferred by N.O.E. experiments. The influence of the chiral carbon atom of the esteric group located at C2 was studied using the diastereotopicity of the protons and of the carbon atoms recorded in high field nmr spectra.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2245 - 2250
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DOI: 10.3987/COM-95-7157
Garcinianin, a Novel Biflavonoid from the Roots of Garcinia kola

Kenji Terashima, Muhd Aqil, and Masatake Niwa*

*Faculty of Pharmacy, Meijo University, Tempaku, Nagoya 468, Japan


A novel biflavonoid named garcinianin was isolated from the roots of Garcinia kola (Guttiferae) and the structure was characterized as a C-3/C-8"-naringenin/kaempferol dimer by spectroscopic methods. Garcinianin is present as a mixture of two atropisomers (relative ratio; 1:1.2) at 25 °C. Garcinianin is the first example of a flavanone-flavonol biflavonoid.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2251 - 2262
Published online:
DOI: 10.3987/COM-95-7163
Polycyclic N-Heterocyclic Compounds. 47 Synthesis and Evaluation of Anti-Platelet Aggregation Activity of 11,13,15-Triazasteroid and Related Compounds

Kenji Sasaki, Tomohiro Funabashi, Hiromi Ohtomo, Taiji Nakayama, and Takashi Hirota*

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


Synthesis and separation of cis- and trans-1,2,4,5,5a,6,7,8,9,9a-decahydrobenz[h]imidazo[1,2-c]quinazolines and its precursors are described. Inhibitory activity against collagen-induced platelet aggregation for rabbit blood of these compounds and their benzologues at A ring is also evaluated.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2263 - 2269
Published online:
DOI: 10.3987/COM-95-7171
Synthesis of 2-Substituted 2,3-Dihydro-1,4-benzothiazine-3-thiones via Iminophosphoranes

Masahiko Takahashi* and Masaru Ohba

*Department of Materials Science, Faculty of Engineering, Ibaraki University, Hitachi, Ibaraki 316, Japan


2-(Substituted methylsulfanyl)anilines (5) were treated with triphenylphosphine dibromide to yield iminophosphoranes (6), whose aza-Wittig reaction with carbon disulfide gave 2-(substituted methylsulfanyl)phenyl isothiocyanates (8). Cyclization of 8 by strong bases afforded 2-substituted 2,3-dihydro-1,4-benzothiazine-3-thiones (10).

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2271 - 2278
Published online:
DOI: 10.3987/COM-95-7172
A Formal Total Synthesis of (+)-Galactostatin via a Tetrahydroxynorleucine Derivative

Mitsunori Kirihata,* Yoshinobu Nakao, Masahiro Mori, and Itsuo Ichimoto

*Department of Applied Biochemistry, College of Agriculture, University of Osaka Prefecture, 1-1 Gakuencho, Sakai, Osaka 593, Japan


(2S,3S,4S,5R)-2,3:4,6-Bis(isopropylidenedioxy)-5-[[(p-methoxybenzyloxy)carbonyl]amino]hexan-1-ol (14), a synthetic intermediate for (+)-galactostatin (1), has been synthesized starting from (+)-diethyl tartarate using the aldol-type condensation of methyl isocyanoacetate (2) with 4-O-benzyl-2,3-O-isopropyliden-L-threose (4) via a 3,4,5,6-tetrahydroxynorleucine derivative (8) as a key reaction.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2279 - 2287
Published online:
DOI: 10.3987/COM-95-7177
A New Synthesis of 3-Substituted Indolines and Indoles

Masaru Kihara,* Yasumasa Iwai, and Yoshimitsu Nagao

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770, Japan


3-Phenyl- and 3-alkyl-3-hydroxyindolines were synthesized by intramolecular Barbier reaction of phenyl and alkyl N-(2-iodophenyl)-N-methylaminomethyl ketones with n-BuLi, which were easily prepared from N-methyl-2-iodoaniline and bromomethyl ketones. The treatment of the indolines with acid gave the corresponding indoles in quantitative yields.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2289 - 2298
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DOI: 10.3987/COM-95-7180
Reactions of 2-Alkylamino- and 2-Dialkylamino-1-azaazulenes with Diphenylcyclopropenone

Noritaka Abe,* Toshihiro Murafuji, Yoshikazu Sugihara, and Akikazu Kakehi

*Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753, Japan


Reaction of 2-alkylamino-1-azaazulenes with DPP gave 1,2-diphenyl-3H-9-azacyclopent[a]azulen-3-one and N-alkyl-N-(1-azaazulen-2-yl)-2,3-diphenyl-2-propenamides. Reaction of 2-dialkylamino-1-azaazulenes with DPP gave 2-dialkylamino-4,5-diphenyl-7H-1-azacyclopent[e]azulen-7-ones 2-dialkylamino-3,4-diphenyl-5H-1-azabenz[cd]azulen-5-ones. Some structures of the products were determined by single-crystal X-ray structure analyses.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2299 - 2306
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DOI: 10.3987/COM-95-7181
Fused [1]Benzazepines. Pentacyclic [1]Benzazepines by Reaction of 1H-[1]Benzazepine-2,5(3H,4H)-dione with Aldehydes

Conrad Kunick*

*Institut für Pharmazie, Universität Hamburg, 20146 Humburg, Germany


Condensation reaction of 1H-[1]benzazepine-2,5(3H,4H)-dione (1) with the aromatic aldehydes (2a-e) in the presence of piperidine furnished 4-benzylidene-1H-[1]benzazepine-2,5(3H,4H)-diones (3a-e), whereas in the presence of potassium hydroxide the 7a,8,15a,15b-tetrahydro-15b-hydroxy-5H-[1]benzazepino[4’,5’:4,5]cyclopenta[1,2-c][1]benzazepine-6,9,15(7H,8aH,14H)-triones (4a-e) were formed. The reaction of 1 with formaldehyde yielded the spiro compound (7) as the product of a Diels-Alder dimerization.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2307 - 2312
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DOI: 10.3987/COM-95-7186
Formations of Organic Semiconductors: Bistropylium Ions Linked by Heterocyclic Moieties as Components of Charge Transfer Complex

Kazuaki Ito and Katsuhiro Saito*

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


Bistropylium ions linked by heterocyclic moieties were synthesized to measure their reduction potentials of -0.47 ~ -0.42 V vs. SCE. Charge transfer complexes between these bistropylium ions and radical anion of TCNQ showed conductivities of 7.7 X 10-4 ~ 7.7 X 10-5 Scm-1, indicating that they can be classified as semiconductors.

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Paper | Regular issue | Vol 41, No. 10, 1995, pp. 2313 - 2326
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DOI: 10.3987/COM-95-7191
Paratocarpins F - L, Seven New Isoprenoid-substituted Flavonoids from Paratocarpus venenosa Zoll

Yoshio Hano, Naoyuki Itoh, Akio Hanaoka, and Taro Nomura*

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


Two new isoprenoid substituted chalcones, paratocarpins F (1) and G (2), along with five new isoprenoid substituted flavanones, paratocarpins H (3), I (4), J (5), K (6), and L (7), were isolated from the Indonesian moraceous plant, Paratocarpus (= Artocarpus) venenosa Zoll. The structures of paratocarpins F, G, H, I, J, K, and L were shown to be 1, 2, 3, 4, 5, 6, and 7, respectively, on the basis of spectroscopic and chemical evidence.

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Review | Regular issue | Vol 41, No. 10, 1995, pp. 2327 - 2356
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DOI: 10.3987/REV-95-470
Heterocyclic Saturated Compounds as Derivatives or Precursors of Chloromycetine and of Some Related Structures

Mircea Darabantu, Sorin Mager, Gérard Plé, and Camelia Puscas*

*University Babes-Bolyai Cluj-Napoca, Department of Organic Chemistry, 11 Arany Ianos str., 3400 Cluj-Napoca, Romania


The review summarizes the diastereoselective synthesis of chloromycetine, of its cyclic acetals or ketals and related structures via 1,3-dioxanes, oxazolidines and 1,2-epoxides.

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Review | Regular issue | Vol 41, No. 10, 1995, pp. 2357 - 2386
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DOI: 10.3987/REV-95-474
Heterocycles from Intramolecular Wittig, Horner and Wadsworth-Emmons Reactions

B. Mark Heron*

*Department of Chemistry, University of Central Lancashire, Preston, Lancashire, PR1 2HE, England


The synthesis of a range of heterocyclic systems based on intramolecular reactions of phosphorus ylides and phosphinoxy and phosphonate carbanions is reviewed.

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22 data found. 1 - 22 listed