Regular Issue

Vol. 51, No. 11, 1999

23 data found. 1 - 23 listed
Communication | Regular issue | Vol 51, No. 11, 1999, pp. 2553 - 2556
Published online:
DOI: 10.3987/COM-99-8650
The Supramolecular Structure of 1,4-Bis-(9-fluorenyl)-1,4-dihydro[60]fullerene with Hexahomotrioxacalix[3]arene in the Solid State

Kazunori Tsubaki, Yasujiro Murata, Koichi Komatsu, Takayoshi Kinoshita, and Kaoru Fuji*

*Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan


The X-Ray analysis disclosed the structure of the suprarnolecular complex of 1,4-bis(9-fluorenyl)-1,4-dihydro[60]fullerene with p-bromo-hexahomotrioxacalix[3]arene.

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Communication | Regular issue | Vol 51, No. 11, 1999, pp. 2557 - 2560
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DOI: 10.3987/COM-99-8697
Synthesis of 9-Ethoxycarbonyl-10(10aH)-oxo-5,6,7,8,8a,9-hexahydro-9,10a-anthracenecarbolactone and Related Compounds by Manganese(III) Mediated Cyclization

Shunsaku Ohta,* Takahiro Kajiura, Hiromichi Murai, Masayuki Yamashita, and Ikuo Kawasaki

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


Novel tetracyclic lactone (5a), 9-ethoxycarhonyl-10(10aH)-oxo-5,6,7,8,8a,9-hexahydro-9,10a-anthracenecarbolactone, was obtained in 34.8% yield by oxidative cyclization of diethyl trans-2-benzoylcyclohexylmalonate (4a) with manganese(III) acetate dihydrate in the presence of sodium acetate in acetic acid.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2561 - 2573
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DOI: 10.3987/COM-99-8585
Synthesis and Antihistaminic H1 Activity of 1,2,5(6)-Trisubstituted Benzimidazoles

Hakan Göker,* Gülgün Ayhan-Kilcigil, Meral Tunçbilek, Canan Kus, Rahmiye Ertan, Engin Kendi, Süheyla Özbey, Mercé Fort, Celia Garcia, and Antonio J. Farré

*University of Ankara, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 06100 - Tandogan, Ankara, Turkey


A number of benzimidazoles, having several substituents on the azole and benzene nuclei and C-2 (methylamino, ethylenediamine, morpholine, piperazine and piperidine) were prepared. Regioselective synthesis was designed for the N1-alkyl substituted benzimidazoles (14-15). X-Ray structure analysis of (14) was also revealed. Compounds were evaluated for their in vitro H1-antihistaminic activity in the isolated guinea-pig ileum method. The compound (11) exhibits best activity.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2575 - 2588
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DOI: 10.3987/COM-99-8609
The Conformational Preference of SomeTetrahydropyrrolo[1,2-d][1,3,4]oxadiazine Derivatives as Studied by NMR Spectroscopy and X-Ray Analysis

Ari Rosling, Karel Klika, Ferenc Fülöp, Reijo Sillanpää, and Jorma Mattinen*

*Department of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Åbo, Finland


Diastereomers (4S,4aS)- and (4R,4aS)- 2,4-diphenyl-4H-4a,5,6,7-tetrahydropyrrolo[1,2-d][1,3,4]oxadiazine and their 2,4,4-triphenylsubstituted analogue were synthesised. Their conformational behaviour, elucidated by means of NMR spectroscopy and X-Ray analysis, revealed some surprising features. The unsubstituted parent compound (4aS)-2-phenyl-4H-4a,5,6,7-tetrahydropyrrolo[1,2-d][1,3,4]oxadiazine was shown, by X-Ray analysis to adopt the same conformational preference in the solid state as in solution, the cis N-out conformation. However both (4S,4aS)- 2,4-diphenyl-4H-4a,5,6,7-tetrahydropyrrolo[1,2-d][1,3,4]oxadiazine and its 2,4,4-triphenyl-substituted analogue adopted a trans conformation in the solid state, in contrast to their predominant cis conformations adopted in solution. The determination of the conformation in solution rewuired the examination of several parameters including homonuclear NOEs, vicinal H,H and H,C, coupling constants, the 2JH-7α,H-7β value, the δδ H-7α,H-7β value, δ H4a, and the 15N chemical shift of the bridgehead nitrogen.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2589 - 2602
Published online:
DOI: 10.3987/COM-99-8622
The Preparation of Pyridine-carboxylates from Chloropyridines by the Palladium-catalyzed Alkoxycarbonylation

Yves Bessard* and Roger Crettaz

*Department of Process Research, LONZA Ltd., P.O. box CH-3930 Visp, Switzerland


The preparation of pyridinecarboxylates and pyridinedicarboxylates by alkoxycarbonylation of chloropyridines with carbon monoxide in the presence of palladium acetate and 1,1’-bis(diphenylphosphino)ferrocene is described. The process uses readily available starting materials and affords pyridinecarboxylates in good to very good yields.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2603 - 2618
Published online:
DOI: 10.3987/COM-99-8641
Synthesis of Losoxantrone Metabolites Isolated from Human Urine

Jung-Hui Sun,* Jiasheng Yan, Zelleka Getahun, Michael A. Vavala, and Gregory A. Nemeth

*The DuPont Pharmaceuticals Company, Experimentall Station, P.O. Box 08336, Route 141 & Henry Clay road, Wilmington, DE 19880-0336, U. S. A.


The first regiospecific synthesis of the monoacid metabolites (2) and (3) of losoxantrone is reported. In addition, synthesis of the diacid metabolite (4) via two different routes is also described. The chemical structures of these metabolites as well as their intermediates have been fully characterized.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2619 - 2625
Published online:
DOI: 10.3987/COM-99-8651
Cytotoxic Briarane Diterpenes from a Gorgonacean Briareum sp.

Tetsuo Iwagawa,* Keita Takayama, Hiroaki Okamura, Munehiro Nakatani,* Matsumi Doe,* Kaoru Takemura,* and Motoo Shiro*

*Department of Chemistry and Bioscience, Faculty of Science, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan


Four new briarane diterpenes violides J-M (1-4), possessing a 8,17-dihydroxyl group, have been isolated from a gorgonacean Briareum sp. Their structures were established by spectral methods and a single crystalline X-Ray analysis. Twelve violides so far isolated from the gorgonian were performed on biological activity tests.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2627 - 2638
Published online:
DOI: 10.3987/COM-99-8653
Palladium(0)-catalyzed Coupling of 6-Bromo and 3-Iodo Derivatives of 7-Methyl-4-oxo-1,4-dihydro[1,8]naphthyridines

Christophe Plisson and Jacques Chenault*

*Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d'Orléans, BP 6759, Rue de Chartres, 45067 Orléans Cédex 2, France


Substituted 4-oxo-1,4-dihydro[1,8]naphthyridines were obtained with various substituents (aryl, alkyl, carbonyl chains) by functionalization at positions 6 and 3 using a Suzuki, Heck or Stille reaction.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2639 - 2651
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DOI: 10.3987/COM-99-8663
Synthesis of New Spiropyrans and Spirooxazines Having a Heteroaromatic Pendant and Their Photochromic Behavior

Xiaoliu Li, Yongmei Wang, Teruo Matsuura, and Jiben Meng*

*Department of Chemistry, Nankai University, Tianjin 300071 P. R., China


Two series of novel spiropyrans and spirooxazines having a heteroaromatic pendant were synthesized using two convenient methods. Their photochromic behaviors were investigated with the aid of absorption spectral measurements. The compounds showed several features different from the parent Spiro compounds, including an inhibitory effect on the fatigue during the photochromic process of spiropyrans.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2653 - 2666
Published online:
DOI: 10.3987/COM-99-8666
A Facile Synthesis of N-Arylcyanoformamidoximes, 4-Aryl-3-cyano-1,2,4-oxadiazin-5(6H)-ones, 2-Cyanoquinazoline-3-oxides, and 2-Cyanoquinazolines via 5-Arylimino-4-chloro-5H-1,2,3-dithiazoles

Yong-Goo Chang and Kyongtae Kim*

*Department of Chemistry, Seoul National University, San 56-1, Shillim-Dong, Kwanak-Gu, Seoul 151-742, Korea


The reaction of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with hydroxylamine hydrochloride in pyridine at room temperature gave N-arylcyanoformamidoximes, which were utilized as starting materials for the synthesis of 4-alkyl- (or aryl)-2-cyanoquinazolines and 4-aryl-3-cyano-1,2,4-oxadiazin-5(6H)-ones.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2667 - 2673
Published online:
DOI: 10.3987/COM-99-8675
Silver(I) Ion-mediated Desulfurization-Cyclization of Isothiocyanates with Several Hydroxy Acids and N-Substituted Amino Acids

Isao Shibuya,* Midori Goto, Masao Shimizu, Masaru Yanagisawa, and Yuasuo Gama

*National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan


The title reaction of 2-hydroxy-2-methylpropionic acid with phenyl isothiocyanate gave 5,5-dimethyl-3-phenyl-2,4-oxazolidinedione. The structure was determined by X-Ray crystal analysis, and the reaction pathway was estimated. The reactions of other 2-hydroxyl acids with isothiocyanates also gave some 2,4-oxazolidinediones in good yields. 3-Hydroxybutyric acid, salicylic acid, 3-hydroxy-2-naphthoic acid, and 3-hydroxypyridine-2-carboxylic acid afforded the corresponding cyclic products through the desulfurization-cyclization with isothiocyanate, respectively. N-Substituted amino acids gave several imidazolidine-2,4-diones in the same way.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2675 - 2686
Published online:
DOI: 10.3987/COM-99-8683
Reactions of β-Aminoenones with Acetylhydrazine, Semicarbazide and Methoxycarbonylhydrazine. Synthesis of 1-Acetyl-, 1-Carboxamide- or Methyl 1-Carboxylated Pyrazole Derivatives

Angel Alberola,* Luis Calvo, Alfonso González Ortega, M. Luisa Sádaba, M. Carmen Sañudo, Santiago García Granda, and Elena García Rodríguez

*Departamento de Química OrgÁnica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid, Spain


Acetyihydrazine, semicarbazide and methoxycarbonyihydrazine react with β-aminoenones to give regioselectively the corresponding N-acetyl- or N-carboxypyrazole derivatives. The reaction are highly regioselective and occurs via 5-hydroxypyrazolines which in several case can be isolated and characterized.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2687 - 2695
Published online:
DOI: 10.3987/COM-99-8684
Condensation Reactions of a Nitrodienamine with Grignard and Organocopper Reagents Prepared from Indole Derivatives

Takeshi Koike,* Naoki Takeuchi, Masanori Hagiwara, Kaori Yamazaki, and Seisho Tobinaga

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


Condensation reactions of a nitrodienamine (1) with Grignard and organocopper reagents prepared from indole derivatives were investigated. Indolyl Grignard reagents were prepared from 4-bromoindole (3a), 5-bromoindole (3b), 6-bromoindole (3c), and 5-nitroindole (3d) using methylmagnesium bromide. Indolyl organocopper reagents were prepared from indole (3e), 2-methylindole (3f), and 3-methylindole (3g) using dimethylcopperlithium.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2697 - 2702
Published online:
DOI: 10.3987/COM-99-8691
A Simple and Efficient Synthetic Method for Fluorine-containing Benzo[b][1,10]phenanthrolines

Etsuji Okada,* Norikado Tsukushi, and Takushi Sakaemura

*Department of Chemical Science andd Engineerring, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


Acid-catalyzed cyclization of N-aryl-5,7-bis(trifluoroacetyl)-8-quinolylamines (2), prepared by aromatic nucleophilic nitrogen-nitrogen exchange reaction of N,N-dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine (1) with p-substituted anilines, afforded fluorine-containing benzo[b][1,10]phenanthrolines (3) in excellent yields.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2703 - 2710
Published online:
DOI: 10.3987/COM-99-8695
Diels-Alder Reaction of Pyrano[3,4-b]indolones with an Electron-deficient Pyridazinone: A New Pathway to Carbazole-fused Pyridazines

Norbert Haider,* Johann Käferböck, and Péter Mátyus

*Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse14, A-1090 Vienna, Austria


Thermally induced [4+2] cycloaddition reactions of 5-ethane-sulfonyl-2-methylpyridazin-3(2H)-one (2) with pyrano[3,4-b]-indol-3(9H)-ones (1, 4) affords isomeric pyridazino[4,5-b]carbazolones (3a,b, 5a,b), the product ratio depending on the substitution pattern of the diene. Two carbazolo-carbazoles (6, 7) were obtained as side products.

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Paper | Regular issue | Vol 51, No. 11, 1999, pp. 2711 - 2722
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DOI: 10.3987/COM-99-8698
Radical Cyclization in Heterocycle Synthesis. 7. Synthesis of Chiral 2-Substituted 5-Amino-4-piperidinols via Radical Cyclization

Toshiko Kiguchi, Miyuki Okazaki, and Takeaki Naito*

*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan


Oxime ether connected by a tether to formal group, which is available from natiral amino acid, efficiently cyclizea via stannyl radical addition-cycluzation od SmI2-induced radical reaction to provide a new entry asymmetric synthesis of 2-substituted 5-amino-4-piperidinols.

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Note | Regular issue | Vol 51, No. 11, 1999, pp. 2723 - 2729
Published online:
DOI: 10.3987/COM-99-8654
Synthesis of Some 4-Bromopyrimidines and Condensed 4-Bromopyrimidines by One-Pot Reaction

Mahesh. T. Chhabria* and Chamanlal J. Shishoo

*Department of Pharmaceutical Chemistry, L. M. College of Pharmacy, P.O.Box 4011, Navrangpura, Ahmedabad - 380 009 Gujarat, India


Simple one-pot reaction has been developed for the synthesis of 4-bromopyrimidines and condensed 4-bromopyrimidines. Under the catalytical influence of dry hydrogen bromide, N-(cyanovinyl)amidines cyclised to 4-bromopyrimidines, and 2-aminonitrile compounds with halogenoacetonitriles gave condensed 4-bromopyrimidines, in good yields.

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Note | Regular issue | Vol 51, No. 11, 1999, pp. 2731 - 2738
Published online:
DOI: 10.3987/COM-99-8655
Synthesis of 3-Alkylsulfinyl-4(1H)-quinolinones from 4-Methoxy-3-alkylthioquinolines

Magdalena Rudnik and Andrzej Maslankiewicz*

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska Str. 4, 41-200 Sosnowiec, Poland


Reactions of 4-methoxy- or 1,4-dihydro-4-oxo-3-alkylthioquinolines (1) and (4, 5) with a nitrating mixture ran as the 3-alkylthio group S-monooxidation and led to the respective alkylsulfinyl derivatives (2, 3 or 6). Hydrolysis of 4-methoxy-3-alkylsulfinylquinolines (2) with hydrochloric acid (1:1) at 65-68 °C gave 3-alkylsulfinyl-4(1H)-quinolinones (3).

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Note | Regular issue | Vol 51, No. 11, 1999, pp. 2739 - 2746
Published online:
DOI: 10.3987/COM-99-8664
The Synthesis and Characteristics of Macrocyclic Compounds Containing 5- Mercapto-3H-1,3,4-thiadiazolin-2-one Subunits

Nam Sook Cho,* Chang Kwon Park, Hyun Sook Kim, Jing Gab Oh, Il Hwan Suh, and Mi Ran Oh

*Department of Chemistry, College of Natural Sciences, Chungnam National University, Taejon 305-764, Korea


The synthesis of six new macrocyclic compounds (5) containing two 5-mercapto-3H-1,3,4-thiadiazolin-2-one (1) subunits linked to the 3 and 5 positions of the heterocyclic units is described. The formation of a complex of 5d with Ag+ is also reported.

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Note | Regular issue | Vol 51, No. 11, 1999, pp. 2747 - 2752
Published online:
DOI: 10.3987/COM-99-8671
On the Facile Dimerization of Precocene II

Braulio M. Fraga,* Inmaculada Cabrera, and Víctor P. García

*Instituto de Productos Naturales y Agrobiologia de Canrias, C. S. I. C., P.O. Box 195, 38206- La Laguna, Tenerife, Spain


The AgNO3-silica gel dimerization of precocene II (2) has been restudied in order to identify minor products. The transformation of dimer B (9) into other dimeric compounds has also been examined.

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Note | Regular issue | Vol 51, No. 11, 1999, pp. 2753 - 2758
Published online:
DOI: 10.3987/COM-99-8673
1-Phenyl-2-(1-pyrrolidinyl)-1-propanol as a Chiral Catalyst for the Highly Enantioselective Addition of Dialkylzincs to Five-membered Heterocyclic Aldehydes

Itaru Sato, Takahiro Saito, Daisuke Omiya, Yoshiko Takizawa, and Kenso Soai*

*Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan


(1S, 2R)- and (1R, 2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol catalyze the enantioselective addition of dialkylzincs to furaldehydes, thiophenecarbaldehydes, and 1-(p-tosyl)-2-pyrrolecarbaldehyde to afford the corresponding enantiomerically enriched sec-alcohols with up to 87% enantiomeric excess.

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Note | Regular issue | Vol 51, No. 11, 1999, pp. 2759 - 2764
Published online:
DOI: 10.3987/COM-99-8686
Two New Erythrinan Alkaloids from Erythrina x bidwillii

Hitoshi Tanaka,* Toshihiro Tanaka, Hideo Etoh, Sachiko Goto, and Yukimasa Terada

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


Two new erythrinan alkaloids, 10,11-dioxoerythraline (1) and 8-oxoerythraline epoxide (5) have been isolated from flowers of Erythrina x bidwillii. Their structures were elucidated by spectroscopic analyses and chemical evidence. 8-Oxoerythraline epoxide is the first erythrinan alkaloid possessing an epoxy ring.

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Note | Regular issue | Vol 51, No. 11, 1999, pp. 2765 - 2774
Published online:
DOI: 10.3987/COM-99-8687
Synthesis of Some New Imidazo[1,2-c]pyrimido[4’,5’:6,5]pyrano[3,2-h]quinoline Derivatives

Marzoog S. Al-Thebeiti

*Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah Almukkarramah, P. O. Box 6876, Saudi Arabia


5-Dimethylaminosulfonyl-8-quinolinol (1) was reacted with cinnamonitriles (2a,b) to give the corresponding pyranoquinolines (3a,b). Reaction of 3a,b with ethylenediamine yielded 2-amino-4-aryl-3-(4,5-dihydro-1H-imidazol-2-yl)pyrano[3,2-h]quinolines (4a,b). Compounds (4a,b) were reacted with triethyl orthoformate, aldehyde, ketone and carbon disulfide to give the corresponding imidazo[1,2-c]pyrimido[4’,5’:6,5]pyrano[3,2-h]quinoline derivatives (5a,b-15a,b).

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23 data found. 1 - 23 listed