Regular Issue

Vol. 63, No. 9, 2004

16 data found. 1 - 16 listed
Communication | Regular issue | Vol 63, No. 9, 2004, pp. 2005 - 2011
Published online: 30th July, 2004
DOI: 10.3987/COM-04-10145
Synthesis of Molecular Tweezers Bearing Two Porphyrins and Its Complexation toward Electron Acceptors

Hajime Iwamoto, Masaki Yamaguchi, Saki Hiura, and Yoshimasa Fukazawa*

*Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan


Synthesis of new flexible molecular tweezers 1·M2 (M = 2H, Co, Zn, Cu, Ni) based on bis-dioxa[2.2]orthocyclophane bearing two porphyrins is presented. The molecular tweezers (1·(2H)2) can bind not only planar π-electron acceptors, such as tetracyanoquinodimethane (TCNQ) and tetracyanobenzene (TCNB) but also a spherical guest C60.

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Paper | Regular issue | Vol 63, No. 9, 2004, pp. 2013 - 2017
Published online: 3rd August, 2004
DOI: 10.3987/COM-04-10121
KAl(SO4)2·12H2O: An Efficient Catalyst for the Stereoselective Synthesis of cis-Isoquinolonic Acids

Javad Azizian,* Ali A. Mohammadi, Ali R. Karimi, Mohammad R. Mohammadizadeh, and M. Koohshari

*Department of Chemistry, Faculty of Science, Shahid Beheshti University, P. O. Box 19395-4716 Tehran, Iran


KAl(SO4)2·12H2O is found to catalyze efficiently the stereoselective cyclocondensation of homophthlic anhydride with imines under mild conditions to afford the corresponding cis-isoquinolonic acids in good yields.

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Paper | Regular issue | Vol 63, No. 9, 2004, pp. 2019 - 2032
Published online: 26th July, 2004
DOI: 10.3987/COM-04-10130
Synthesis of 2,3-Dihydro-4(1H)-quinazolinones

Jaime Escalante,* Patricia Flores, and Jaime M. Priego

*Chemical Research Center, Morelos Autonomous State University, Av. Universidad No. 1001, Colonia Chamilpa, C.P. 62210 Cuernavaca-Morelos, Mexico


An improved procedure for the synthesis of 2-substituted 2,3-dihydro-4(1H)-quinazolinones through diastereomer separation of the corresponding quinazolinones derivatives is presented. The determination of their absolute configurations was obtained by X-Ray diffraction.

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Paper | Regular issue | Vol 63, No. 9, 2004, pp. 2033 - 2041
Published online: 23rd August, 2004
DOI: 10.3987/COM-04-10133
New Pyridinium Chiral Ionic Liquids

Cosmin Patrascu, Claudia Sugisaki, Christophe Mingotaud, Jean-Daniel Marty, Yves Génisson, and Nancy Lauth - de Viguerie*

*Laboratory of IMRCP, UMR 5623 CNRS, Paul Sabatier University, 118 route de Narbonne, 31062 Toulouse cedex 04, France


New pyridinium chiral ionic liquids have been synthesised from the corresponding pyridine and chiral primary amines. The physical properties of these salts were determined; one of the salts is a room-temperature ionic liquid thermally stable up to 215 °C and suitable for organic synthesis.

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Paper | Regular issue | Vol 63, No. 9, 2004, pp. 2043 - 2050
Published online: 30th July, 2004
DOI: 10.3987/COM-04-10146
Sarcodifurines A and B, Two New Furoquinolines from Sarcomelicope follicularis

Elizabeth Chosson,* Anne-Emmanuelle Hay, Angele Chiaroni, Anne Favel, François Tillequin, Marc Litaudon, and Elisabeth Seguin

*Department of Botany, UFR of Medicine and Pharmacy, 22 Bd Gambetta F-76183 Rouen cedex 1, France


Two novel furoquinolines, named sarcodifurine A (1) and B (2) were isolated from the leaves of Sarcomelicope follicularis (Rutaceae). The structures were elucidated on the basis of spectroscopical data, especially 2D-HMBC and HMQC NMR experiments. The relative configurations were unambiguously determined by single-crystal X-Ray diffraction analyses.

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Paper | Regular issue | Vol 63, No. 9, 2004, pp. 2051 - 2056
Published online: 30th July, 2004
DOI: 10.3987/COM-04-10155
Formation of a Sixteen-membered Ring by Condensation of N,N ’-Dimesityl-propane-1,3-diamine with Triethyl Orthoformate and Ammonium Tetrafluoroborate

Andreas L. Paulsen and Robert Madsen*

*Department of Chemistry, Building 201, Technical University of Denmark, DK-2800 Lyngby, Denmark


Cyclocondensation of N,N’-dimesityl-propane-1,3-diamine with triethyl orthoformate and ammonium tetrafluoroborate gave as the major product macrocycle (2) under neat conditions and 1,3-dimesityl-3,4,5,6,-tetrahydro-pyrimidin-1-ium tetrafluoroborate with ethanol as the solvent. The structures of the two ring systems were confirmed by X-Ray diffraction analysis.

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Paper | Regular issue | Vol 63, No. 9, 2004, pp. 2057 - 2070
Published online: 3rd August, 2004
DOI: 10.3987/COM-04-10161
Conformational Analysis of Tricyclic Ketolide TE-802 and Its Analogues

Masato Kashimura,* Keita Matsumoto, Toshifumi Asaka, and Shigeo Morimoto

*Medicinal Research Laboratories, Taisho Pharmaceutical Co., Ltd., 1-403 Yoshino-Cho, Kita-ku, Saitama-shi, Saitama 331-9530, Japan


The conformations of tricyclic ketolide TE-802 (1) and its analogue were determined by crystallographic analysis and NMR spectroscopy. The 3-carbonyl function of 1 took an ‘exo’ orientation against the lactone ring, and the orientation of the amino sugar at the 5-position differed from that in clarithromycin (CAM:2). On the other hand, di- and tricyclic ketolides and a tricyclic macrolide were found to exist in ‘semi-fold-out (4H-downward)’ conformation in deuteriochloroform. The conformation of 1 in deuteriochloroform was closely similar to that in D2O. The newly formed tetrahydrodiazepine ring existed in chair form or boat form, governed by the presence of a substituent and its position.

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2071 - 2077
Published online: 16th July, 2004
DOI: 10.3987/COM-04-10124
Synthesis of 5-Benzoyl-6-trifluoromethyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic Acid

Adrián Covarrubias Zúñiga

*Institute of Chemistry, Autonomous National University of México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, Mexico


Synthesis of the possible analgesic and/or antiinflammatory agent 5-benzoyl-6-trifluoromethyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid (1) was designed from the already known intermediate ester 3-methoxycarbonyl-4-trifluoromethyl-5-benzyloxycarbonylpyrrole-2-acetic acid methyl ester (4) wich is prepared via a Knorr synthesis.

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2079 - 2086
Published online: 16th July, 2004
DOI: 10.3987/COM-04-10129
Study on Syntheses and Structure of a New Kind of Bis-heterocyclic Thiadiazine Derivatives Containing Pyrazolone

Guang-Fei Liu, Lang Liu, Dian-Zeng Jia,* Bang-Hua Peng, Xin Hu, and Kai-Bei Yu

*Institute of Applied Chemistry, Xinjiang University, Urumqi 830046, China


A new kind of bis-heterocyclic thiadiazine derivatives containing pyrazolone were synthesized and characterized. 2-Methylthio-5-(1,3-diphenyl- 5-pyrazolone-4-ylidene)-5,6-dihydro-4H-1,3,4-thiadiazine (DPCP-MTTSC) (5) was determined by X-Ray crystallographical analysis.

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2087 - 2090
Published online: 26th July, 2004
DOI: 10.3987/COM-04-10140
New O-Terpenoidal Coumarins from Clausena excavata

Hong Ping He, Yue Mao Shen, Zhi Zhi Du, Yi Bin Zhao, and Xiao Jiang Hao*

*The State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, The Chinese Academy of Sciences, Kunming 650204, Yunnan, China


Chemical investigation on an ethanol extract from the aerial part of Clausena excavata resulted in the isolation of two new O-diterpenoidal coumarins, excavacoumarins H (1) and I (2).

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2091 - 2095
Published online: 26th July, 2004
DOI: 10.3987/COM-04-10150
A New Prenylated Flavone from the Leaves of Glycyrrhiza uralensis Cultivated in China

Hong Bai, Wei Li, Kazuo Koike, Yuping Pei, Deqiang Dou, Yingjie Chen, Yinghua Wang, and Tamotsu Nikaido*

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


A new prenylated flavone, 6,5’-diprenylluteolin (1), together with three known compounds chrysoeriol (2), kaempferol 3-O-glucoside (3), quercetin 3-O-glucoside (4) was isolated from the leaves of Glycyrrhiza uralensis cultivated in China. The structure of 1 was established on the basis of spectroscopic evidence.

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2097 - 2100
Published online: 26th July, 2004
DOI: 10.3987/COM-04-10154
Enantioselective Hydrogenation of 3,4-Dihydro-β-carbolines Catalyzed by Ir Complexes of Diphosphine

Toshiaki Morimoto,* Naoaki Suzuki, and Kazuo Achiwa

*School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka-shi 422-8526, Japan


A catalytic system, Ir(I)-BINAP-tetrafluorophthalimide, was found to be very efficient in the asymmetric hydrogenation of 3,4-dihydro-1-methyl-β-carbolines, showing high enantioselectivity of 95% ee.

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2101 - 2109
Published online: 6th August, 2004
DOI: 10.3987/COM-04-10157
Two Sesquiterpene-Coumarins from the Roots of Ferula marmarica

Mohamed H. Abd El-Razek, Fang-Rong Chang, Chih-Chuang Liaw, Mahmoud I. Nassar, Hui-Chi Huang, Yung-Husan Chen, Yu-Liang Yang, and Yang-Chang Wu*

*Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, R.O.C.


Two new sesquiterpene-coumarin conjugates designated foetidin acetate and foetidone were isolated from the roots of Ferula marmarica. The structures of the sesquiterpene-coumarins have been fully characterized by spectroscopic methods, among which foetidin acetate was confirmed by single-crystal X-Ray crystallography. Absolute configuration of both new compounds was established by CD.

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2111 - 2122
Published online: 6th August, 2004
DOI: 10.3987/COM-04-10162
Synthesis of Mycalamide Analogs

Shunya Takahashi, Akihiro Okada, and Tadashi Nakata*

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


Several new artificial analogs (3-6) of mycalamide A (1), a potent antiviral and antitumor agent, were synthesized through a coupling reaction of a bicyclic amine (19) with two tetrahydropyrancarboxylic acids (15) and (18), and their cytotoxicity and antiviral activity were tested.

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Note | Regular issue | Vol 63, No. 9, 2004, pp. 2123 - 2129
Published online: 6th August, 2004
DOI: 10.3987/COM-04-10167
Eurycomalin A, a New Dimeric Dihydrobenzofuran from Eurycoma longifolia

Ping-Chung Kuo, Chung-Ren Su, Amooru G. Damu, and Tian-Shung Wu*

*Department of Chemistry, National Cheng Kung University, Tainan, 701, Taiwan, R.O.C.


One new dimeric 2-isopropenyl-2, 3-dihydrobenzofuran, eurycomalin A (1), was characterized from the methanol extract of the root of Eurycoma longifolia by the 1D and 2D spectral and chemical transformation studies. The reported structure of eurycomalide A (2) was revised through detail 2D spectral analyses.

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Review | Regular issue | Vol 63, No. 9, 2004, pp. 2131 - 2158
Published online: 15th June, 2004
DOI: 10.3987/REV-04-579
Rotaxanes Containing Quaternary Azaaromatic Moieties

Wanda Sliwa* and Barbara Bachowska

*Institute of Chemistry and Environmental Protection, Pedagogical University, Al. Armii Krajowej 13/15, 42-201 Czestochowa, Poland


In the paper at first rotaxanes are briefly described, then rotaxanes bearing quaternary azaaromatic moiety in the thread are presented followed by those containing quaternary azaaromatic moiety in the ring.

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16 data found. 1 - 16 listed