Regular Issue

Vol. 63, No. 5, 2004

21 data found. 1 - 21 listed
Communication | Regular issue | Vol 63, No. 5, 2004, pp. 1009 - 1012
Published online: 24th February, 2004
DOI: 10.3987/COM-04-10018
Formation of 3-Pyrrolin-2-ones via 5-Endo-trig Cyclization

Ruri Naitoh, Yayoi Nakamura, Emi Katano, Yohoko Nakamura, Emi Okada, and Morio Asaoka*

*Department of Chemical and Biological Sciences, Faculty of Science, Japan Women’s University, 2-8-1 Mejirodai, Bunkyoku, Tokyo 112-0015, Japan


Anionic cyclization of N-benzyl-3-phenylsulfanyl-2-propenamide derivatives gave the corresponding 3-pyrrolin-2-ones. Mechanistic investigation using deuterated starting materials revealed this cyclization proceeds via a 5-endo-trig process.

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Communication | Regular issue | Vol 63, No. 5, 2004, pp. 1013 - 1016
Published online: 12th March, 2004
DOI: 10.3987/COM-04-10030
Convenient Synthesis of Pulchellalactam, a CD45 Protein Tyrosine Phosphatase Inhibitor from the Marine Fungus Corollospora pulchella, and Its Related Compounds

Jun-ichiro Bessho, Yasuhiko Shimotsu, Sachiko Mizumoto, Nobuyuki Mase, Hidemi Yoda, and Kunihiko Takabe*

*Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan


Convenient synthesis of pulchellalactam (1a) and its related compounds was accomplished. Total yields of (Z)-pulchellalactam and (E)-pulchellalactam were 55% for 5 steps and 43% for 8 steps from commercially available and inexpensive citraconic anhydride, respectively.

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Communication | Regular issue | Vol 63, No. 5, 2004, pp. 1017 - 1021
Published online: 8th March, 2004
DOI: 10.3987/COM-04-10034
Palladium(II)-catalyzed Stereocontrolled Cyclization via Hemiacetal Intermediates: Total Synthesis of 5-Epi-prelactone C

Masahiro Miyazawa, Magsarjav Narantsetseg, Hajime Yokoyama, Seiji Yamaguchi, and Yoshiro Hirai*

*Department of Chemistry, Faculty of Science, Toyama University, Gofuku 3190, Toyama 930, Japan


Palladium(II)-catalyzed cyclization of 3,7-dihydroxy-4-methyl-5-octenal derivative was carried out to give 2,3,4,6-tetrasubstituted tetrahydropyran with stereoselective 1,3-chirality transfer in net retention of stereochemistry. The cyclized product was converted into 5-epi-prelactone C.

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Communication | Regular issue | Vol 63, No. 5, 2004, pp. 1023 - 1026
Published online: 26th March, 2004
DOI: 10.3987/COM-04-10055
A Novel Secondary Metabolite from Lethariella sernanderi

Kaoru Kinoshita, Kazuhiko Takatori, Takao Narui, Chicita F. Culberson, Masahiro Hasumi, Yuuichi Nishino, Kiyotaka Koyama, and Kunio Takahashi*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


A novel secondary metabolite, named sernanderin (1), was isolated from a lichen thallus, Lethariella sernanderi. The structure was elucidated on the basis of spectroscopic data, especially 2D-NMR spectrum and X-Ray crystallographic analyses. This compound (1) has a new skeletone as a natural product so far reported.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1027 - 1044
Published online: 24th February, 2004
DOI: 10.3987/COM-03-9978
Palladium-catalyzed Cyclocarbonylation of Unsaturated Alcohols and Amines. Chemoselective Synthesis of Heterocycle-substituted γ- and δ-Lactones and Lactams

Catia Granito, Luigino Troisi,* and Ludovico Ronzini

*Department of Sciences and Biological and Environmental Technologies, University of Lecce, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy


Unsaturated alcohols and amines react with carbon monoxide and hydrogen, in the presence of a catalytic amount of palladium acetate and a phosphine ligand, to afford selectively heterocycle-substituted γ- and δ-lactones and lactams. The distribution of five- and six-membered ring compounds can be modulated by an appropriate combination of solvent and phosphine ligand. The five-membered products are formed in two isomeric forms trans and cis with a modest diasteroselectivity (trans>cis).

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1045 - 1056
Published online: 8th March, 2004
DOI: 10.3987/COM-03-9999
Synthesis of 3-Ferrocenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazoles

Elena Klimova, Tatiana Klimova,* Teresa Ramírez Apan, Antonio Neito Camacho, Rafael Moreno Esparza, Carlos Damian Zea, and Marcos Martínez García

*Faculty of Chemistry, National Autonomous University of Mexico, Cd. Universitaria, Coyoacan, C.P. 04510, Mexico


The reactions of E-2-ferrocenylmethylidenetetralones with hydrazine proceed diastereoselectively, forming the cis isomers of diazatricycles in high yields. The studies of the anti-inflammatory activity of E-2-ferrocenylmethylidenetetralones and N-acetylindazoles showed a moderate activity in a TPA model. The structure of 2-acetyl-3-ferrocenyl-6-methoxy- 3,3a,4,5-tetrahydro-2H-benzo[g]indazole was confirmed by X-Ray diffraction analysis.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1057 - 1065
Published online: 5th March, 2004
DOI: 10.3987/COM-04-10003
KF-Alumina Immobilized in Ionic Liquids: A Novel Heterogeneous Base for Heterocyclization of Alkylsulfanylphenylamines into 1,4-Benzothiazine

Bhupender S. Chhikara, Anil K. Mishra, and Vibha Tandon*

*Dr. B. R. Ambedkar Center for Biomedical Research, University of Delhi, Delhi-110 007, India


A rapid and convenient synthetic methodology for the cyclocondensative transformation of various alkylsulfanylphenylamines with bromoacetyl bromide by supporting on KF-alumina in ionic liquids [bmim][Br] and [bmim][BF4] has been developed to obtain 3-oxo-1,4-benzothiazine in good yields. The product is easily obtained by extraction with ethyl acetate and concentrating under vacuum. Easy recovery of ionic liquid and use in consecutive reactions is also reported.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1067 - 1075
Published online: 5th March, 2004
DOI: 10.3987/COM-04-10006
Facile Synthesis of 4H-1,3-Benzoselenazines by the Aryne Reaction

U. Narasimha Rao, Ramadas Sathunuru, and Edward R. Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275-0314, U.S.A.


Attempts to prepare benzoselenazoles by trapping benzynes with selenoureas failed. These reactions gave instead symmetrically substituted diaryl diselenides. However, when the selenoureas were converted to selenoazadienes, 4H-1,3-benzoselenazines were obtained in excellent yields. Furthermore, addition of the selenium atom of the selenoazadienes occurred regioselectively at the position 1 of 3-methoxybenzyne and 3,4-dimethoxybenzyne.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1077 - 1081
Published online: 26th March, 2004
DOI: 10.3987/COM-04-10010
Organic Reactions in Ionic Liquids: A Simple Highly Regioselective or Regiospecific Substitutions of Benzotriazole

Zhang-Gao Le, Zhen-Chu Chen,* Yi Hu, and Qin-Guo Zheng

*Department of Chemistry, Zhejiang Universityh (XiXi Campus), Hangzhou, Zhejiang 310028, China


In the absence of any added base in ionic liquids [Bmim][BF4], benzotriazole replaces the halogen atom of an α-halogenated ketone or α-halogenated carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer, and 1-chloro-2,4-dinitrobenzene reacted similarly with benzotriazole to afford the N-1-substituted benzotriazole in a good yield. Alkyl halides reacted regioselectively to afford the N-1-alkylbenzotriazole in ratios of more than 15 to 1 over the N-2-isomer.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1083 - 1091
Published online: 5th March, 2004
DOI: 10.3987/COM-04-10021
Synthesis of Fluorescent Derivatization Reagents: Reaction of Isatin with 3-Aryl-7-diethylaminocoumarins and Their Fluorescent Properties

Naozumi Nishizono,* Kazuaki Oda, Yutaka Kato, Kosei Ohno, Masaru Minami, and Minoru Machida

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


Fluorescent derivatization reagents, 3-aryl-7-diethylaminocoumarin derivatives, were synthesized and reacted with isatin to give the adduct. Their fluorescent properties are discussed.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1093 - 1112
Published online: 12th March, 2004
DOI: 10.3987/COM-04-10022
Synthesis of Substituted 1,4-Benzoxazepin-3-one Derivatives

Yann Davion, Gérald Guillaumet, Jean-Michel Léger, Christian Jarry, Brigitte Lesur, and Jean-Yves Mérour*

*Instiut de Chimie Organique et Analytique, C.N.R.S., Unviersité d’Orléans, BP 6759, Rue de Chartres, 45067 Orleans Cedex, France


A synthesis of substituted 1,4-benzoxazepin-3-one is described starting from salicylaldehyde, aniline and chloroacetyl chloride. Use of 2-bromo-3-phenylpropionyl chloride gave access to 2-benzyl-1,4-benzoxazepin-3-one; an addition/elimination sequence afforded the corresponding benzylidene derivative which structure has been confirmed by an X-Ray analysis. Biphenyl substituents were also introduced in position -4 of this scaffold.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1113 - 1122
Published online: 26th March, 2004
DOI: 10.3987/COM-04-10025
A New Synthetic Route to YM087, an Arginine Vasopressin Antagonist

Takashi Tsunoda,* Akihiro Tanaka, Toshiyasu Mase, and Shuichi Sakamoto

*Yamanouchi Pharmaceutical Co., Ltd., Chemical Technology Labs., Yamanouchi Pharmaceutical Co., Ltd., 160-2, Akahama, Takahagi-shi, Ibaraki, Japan


A new synthesis of N-{4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}biphenyl-2-carboxamide monohydrochloride (1, YM087) via new imidazobenzazepine intermediates is described. This method remarkably improves the overall yield of 1 compared to the original synthesis providing a more safe, reliable and cost-efficient approach to 1.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1123 - 1129
Published online: 30th March, 2004
DOI: 10.3987/COM-04-10037
Gliocladins A - C and Glioperazine ; Cytotoxic Dioxo- or Trioxopiperazine Metabolites from a Gliocladium Sp. Separated from a Sea Hare

Yoshihide Usami,* Junko Yamaguchi, and Atsushi Numata

*Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan


New dioxo- or trioxopiperazine metabolites named gliocladins A-C (1 - 3) and glioperazine (4) have been isolated from a strain of Gliocladium sp., originally separated from the sea hare. Their structures have been elucidated by spectroscopic analyses using various NMR spectroscopic techniques. Structurally unique trioxopiperazine (3) exhibited significant cytotoxicity against cultured P388 cells.

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Paper | Regular issue | Vol 63, No. 5, 2004, pp. 1131 - 1142
Published online: 26th March, 2004
DOI: 10.3987/COM-04-10041
Synthesis of Isotope Labeled Me(3a)-13C-Physostigmine and Debromoflustramine B

Martha S. Morales-Ríos,* Norma F. Santos-Sánchez, Yolanda Mora-Pérez, and Pedro Joseph-Nathan

*Departamento de Química, Centro de Investigación y de Estudios Avanzados, I.P.N, Apartado 14-740, México, D.F., 07000, Mexico


A versatile and concise synthetic route for the synthesis of selectively functionalized pyrrolo[2,3-b]indole alkaloid analogues has been developed starting from 3-indolylacetonitriles. Employing this route, physostigmine with 13C-enrichment at Me(3a) (99 atom% 13C) and debromoflustramine B have been prepared.

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Note | Regular issue | Vol 63, No. 5, 2004, pp. 1143 - 1151
Published online: 8th March, 2004
DOI: 10.3987/COM-03-9960
Pyridazine Derivatives and Related Compounds Part 10. Reactions of 3-Diazopyrazolo[3,4-c]pyridazine with Reactive Methylene Compounds and Other Groups

Ali Deeb* and Mahmoud Kotb

*Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt


3-Diazopyrazolo[3,4-c]pyridazine was synthesized and its transformations were investigated. With reactive methylene compounds the corresponding hydrazones and condensed 1,2,4-triazines were formed. With aromatic amines and naphthols the diazo compound was converted into arylazo derivatives. The diazo compound underwent cycloaddition, reacting as a 1,4-dipole to yield cycloaddition products.

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Note | Regular issue | Vol 63, No. 5, 2004, pp. 1153 - 1163
Published online: 5th March, 2004
DOI: 10.3987/COM-03-9974
A Convenient Synthesis of Some New 1,3,4-Benzothiadiazepin-5-ones

Jalal A. Zahara, Bassam A. Abu Thaher, Mustafa M. El-Abadelah,* and Roland Boese

*Institut für Anorganische Chemie, Universität Duisburg-Essen, Campus Essen, Universitätstrasse, 3-5, D-45117 Essen, Germany


A synthesis of new 1,3,4-benzothiadiazepin-5-ones (6a-c) has been achieved via cyclocondensation, promoted by acetic anhydride at reflux, of the corresponding acyclic 2-{[2-oxo-1-(N-arylhydrazono)propan-1-yl]mercapto}benzoic acids (4a-c). Structural assignments of the heterocyclic products (6a-c) are based on analytical, spectral (IR, MS and NMR) and X-Ray crystal structure data.

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Note | Regular issue | Vol 63, No. 5, 2004, pp. 1165 - 1173
Published online: 24th February, 2004
DOI: 10.3987/COM-03-9997
A Solvent-free Method for Substituted Imidazolidin-4-ones Synthesis

Jirí Pospísil and Milan Potácek*

*Department of Organic Chemistry, Faculty of Science, Masaryk University, Kotlárská 2, CZ-61137 Brno, Czech Republic


A new method of the solvent-free synthesis of substituted imidazolidin-4-ones is described. The method is developed for microwave-assisted solvent-free conditions and compared with classical thermally initiated solvent-free conditions. In both cases the reaction proceeds with good yields. However, the reaction under microwave conditions is accelerated six-times. Thermal effect of the microwaves is observed.

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Note | Regular issue | Vol 63, No. 5, 2004, pp. 1175 - 1180
Published online: 19th March, 2004
DOI: 10.3987/COM-04-10012
Synthesis of 1,2,3-Triazoles

Dolly, Belen Batanero, and Fructuoso Barba*

*Departments of Organic and Inorganic Chemistry, University of Alcalá, 28871 Alcalá de Henares (Madrid), Spain


4-Phenyl-1-(p-toluenesulfonamido)-1,2,3-triazole (1) is obtained when phenacyl halides react with tosyl hydrazide in one-pot process.

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Note | Regular issue | Vol 63, No. 5, 2004, pp. 1181 - 1184
Published online: 24th February, 2004
DOI: 10.3987/COM-04-10017
A New Diterpene Alkaloid from Aconitum brunneum Hand-Mazz

Liming Gao, Xiaomei Wei, Xiaoling Jin, and Li Yang*

*National Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, China


A new diterpenoid alkaloid, 3α-hydroxy-12-epi-napelline (1), was isolated from the ethanol extract of the roots of Aconitum brunneum Hand-Mazz along with six known alkaloinds, i.e., 12-epi-napelline (2), liangshanine (3), 12-epi-dehydronapelline (4), songorine (5), aconitine (6) and benzoylaconine (7). The structure of the new compound was elucidated by spectroscopic methods.

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Note | Regular issue | Vol 63, No. 5, 2004, pp. 1185 - 1192
Published online: 12th March, 2004
DOI: 10.3987/COM-04-10027
Synthesis of New Medium Ring Aromatic Lactones via Halocyclization of 2-Hydroxyphenylalkanoic Acid Allylic Esters

David P. Brown* and Lalitha Krishnamurthy

*Department of Chemistry, St. John’s University, 8000 Utopia Parkway, Jamaica, New York 11439, U.S.A.


Stable medium size ring aromatic lactones have been synthesized through electrophilic heteroatom cyclization reactions in moderate yields.

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Review | Regular issue | Vol 63, No. 5, 2004, pp. 1193 - 1220
Published online: 16th February, 2004
DOI: 10.3987/REV-03-572
Synthesis of Heterocyclic Compounds from the Reactions of Dehydroacetic Acid (DHA) and Its Derivatives

Om Prakash,* Ajay Kumar, and Shiv P. Singh

*Department of Chemistry, Kurukshetra University, Kurukshetra, Haryana, 136119, India


3-Acetyl-4-hydroxy-6-methyl-2-oxo-2H-pyran (Dehydroacetic acid, DHA) and its simple derivatives such as 3-cinnamoyl-4-hydroxy-6-methyl-2-oxo-2H-pyrans (Chalcone analogues of DHA) find interesting applications in the synthesis of various heterocyclic compounds. The review highlighting this aspect covers literature up to 2003.

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21 data found. 1 - 21 listed