Regular Issue

Vol. 57, No. 1, 2002

18 data found. 1 - 18 listed
Communication | Regular issue | Vol 57, No. 1, 2002, pp. 1 - 4
Published online:
DOI: 10.3987/COM-01-9362
Synthesis of Ethyl 1,2,3,4-Tetrahydroisoquinoline-1-carboxylates by Pictet-Spengler Condensation Using Phenyliodine(III) Bis(trifluoroacetate)

Iou-Jiun Kang, Huey-Min Wang, Chien-Hsing Su, and Ling-Ching Chen*

*Graduate Institute of Pharmaceutical Sciences , Kaohsiung Medical University,100 Shih Chen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.


Abstract—The reaction of N-sulfonyl-β-phenethylamines with ethyl methylthioacetate using phenyliodine(III) bis(trifluoroacetate) gives moderate to good yields of the corresponding ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylates.

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Communication | Regular issue | Vol 57, No. 1, 2002, pp. 5 - 10
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DOI: 10.3987/COM-01-9381
Heterocyclizations towards 2-Arylbenzimidazoles via Intermolecular Coupling of 2-Nitroanilines and Aryl Aldehydes

Byeong Hyo Kim,* Rongbi Han, Tae Hee Han, Young Moo Jun, Woonphil Baik, and Byung Min Lee

*Department of Chemistry, Kwangwoon University. 447-1, Wolgye-Dong Nowon-ku, Seoul, 139-701, Korea


The reductive intermolecular coupling/heterocyclization reaction between 2-nitroaniline and aromatic aldehydes towards 2-substituted and 1,2-disubstituted benzimidazoles was accomplished in the presence of 2-bromo-2-nitropropane/Zn in a MeOH/CH2Cl2 solution at room temperature.

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Communication | Regular issue | Vol 57, No. 1, 2002, pp. 11 - 16
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DOI: 10.3987/COM-01-9385
Reaction of 2,3-Butanedione with Propylenediamine Observed by 1H-NMR Spectroscopy

Tadatoshi Yamaguchi,* Shigeru Ito, Nobuko Mibu, and Kunihiro Sumoto

*Department of Hygiene, Miyazaki Medical college, Kiyotake-cho, Miyazaki 889-1692, Japan


2,3-Butanedione reacted with propylenediamine to form an initial intermediate : acetylated methyl-N-(3-aminopropyl) imine, which was a geometrical mixture of syn- and anti- isomers. The intermediate isomerized to anti- or syn-form via pyrimidine ring flip on heating. A steric factor of the isomers affected the formation of the final products. The mechanism based on NMR spectroscopy and molecular orbital calculation is proposed.

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Communication | Regular issue | Vol 57, No. 1, 2002, pp. 17 - 20
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DOI: 10.3987/COM-01-9394
A Through-Space Interaction of 3-Benzylthiothieno[3,4-b]indolizine Derivatives Combined by a Highly Flexible Spacer

Akikazu Kakehi,* Suketaka Ito, Hiroyuki Suga, Takeyuki Miwa, Takashi Mori, and Tomoshige Kobayashi

*Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan


Some ethyl 1-benzoyl-3-[(un)substituted benzylthio]thieno[3,4-b]indolizine-9-carboxylates were prepared and their conformations were investigated. In the solid state and the chloroform solution they had stacked structures in which the phenyl ring and the pyridine moiety of theino[3,4-b]indolizine ring are partly overlapped.

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Paper | Regular issue | Vol 57, No. 1, 2002, pp. 21 - 38
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DOI: 10.3987/COM-01-9347
Efficient Synthesis of New Polyfunctionalized Thiadiazaacenaphthylenes from Imidazo[1,2-a]pyridines

Emmanuel Moreau, Jean-Michel Chezal, Caroline Dechambre, Damien Canitrot, Yves Blache, Claire Lartigue, Olivier Chavignon, and Jean-Claude Teulade*

*Faculté de Pharmacie, UMR INSERM 484, 28 Pl. H. Dunant, B. P. 38, 63001 Clermont-Ferrand Cedex 1, France


New heterocycles containing sulfur and nitrogen with an azaindolizine moiety were synthesized. The imidazo[1,2-a]pyridine-2,5-dicarboxylates (9a, b, 10a, b) and 5-formylimidazo[1,2-a]pyridine-2-carboxylates (17a, b) treated with ethyl thioglycolate and lithium hydroxide underwent ring closure yielding the multifunctional[2,3,3]cyclazines (13) and (18). Under similar conditions, the imidazo[1,2-a]pyridinecarbaldehydes (22a, b) and (29a, b) were converted into the linearly cyclized compounds thieno[3,2-b]imidazo[1,2-a]pyridines (23, 31) and a peri annulated product thiadiazaacenaphthylene (30).

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Paper | Regular issue | Vol 57, No. 1, 2002, pp. 39 - 46
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DOI: 10.3987/COM-01-9351
Mono- and Di-substituted 5,6-Diphenyl-3-alkylaminopyridazines Active as ACAT Inhibitors

Lucio Toma,* Maria Paola Giovannoni, Vittorio Dal Piaz, Byoung-Mog Kwon, Young-Kook Kim, Arianna Gelain, and Daniela Barlocco*

*Department o f Organic Chemistry, University of Pavia, Via Taramelli 10, 27100 Pavia, Italy


A series of mono- or di-para-substituted 5,6-diphenyl-3-alkylaminopyridazines were synthesized and their inhibitory activity against acyl-CoA:cholesterol acyltransferase (ACAT) was tested on the enzyme prepared from rat liver microsomes. The compound which combines a chlorine atom on the 6-phenyl ring and a n-hexylamino chain showed a significant enhancement of activity with respect to the unsubstituted derivative. Attempts to correlate the activity of the compounds to their structural features, also through theoretical calculations, are reported.

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Paper | Regular issue | Vol 57, No. 1, 2002, pp. 47 - 54
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DOI: 10.3987/COM-01-9359
Lewis Acid Catalyzed Dimerization of 2-Aminopyrimidine: Synthesis and X-Ray Structures

Miyuki Eiraku Masaki and Mark M. Turnbull*

*Carlson School of Chemistry and Biochmistry, Clark University, 950 Main St., Worcester, MA 01610, U.S.A.


Reaction of 2-aminopyrimidine with HBr and CoBr2 in aqueous solution led to dimerization of the pyrimidine and formation of a new heterotricyclic dication. The material has been characterized by IR spectroscopy, combustion analysis and X-Ray diffraction. Subsequent experiments show that the dimerization also occurs in the absense of CoBr2, although more slowly. The same tricyclic product was isolated as the bromide salt and characterized by IR spectroscopy, combustion analysis and X-Ray diffraction.

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Paper | Regular issue | Vol 57, No. 1, 2002, pp. 55 - 71
Published online:
DOI: 10.3987/COM-01-9363
Synthesis of Melatonin Analogues Derived from Furo[2,3-b]- and [2,3-c]pyridines by Use of a Palladium-Copper Catalyst System

Hervé Van de Poël, Gérald Guillaumet, and Marie-Claude Viaud-Massuard*

*Laboratoire de Chimie Organique, UFR des Sciences Pharmaceutiques, Université de Tours, 31 Avenue de Monge, 37200 Tours, France


2,3,5-Substituted furo[2,3-b]pyridine was synthesised by palladium-catalyzed reaction of 5-bromo-2-hydroxy-3-iodopyridine and phenylacetylene with (Ph3P)2PdCl2, CuI in Et3N. A carbonylative cyclization of 5-hydroxy-2-methoxy-4-(2-phenylethynyl)pyridine with carbon monoxide in methanol with PdCl2, CuCl2 under basic conditions, has been accomplished to prepare methyl 2,5-substituted furo[2,3-c]pyridine-3-carboxylate.

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Paper | Regular issue | Vol 57, No. 1, 2002, pp. 73 - 95
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DOI: 10.3987/COM-01-9365
About Four New Trityl-substituted α-Lactams

Istvan Lengyel,* Victor Cesare, Ian Adam, and Tony Taldone

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


This investigation comprises the synthesis, a description of the physical and spectroscopic properties, determination of the limits of thermal stability, and reactions with protic and aprotic nucleophiles of four new trityl-substituted α-lactams. With the exception of 3,3-dimethyl-1-tritylaziridin-2-one (4a), which is unstable at room temperature, all new compounds have been fully characterized.

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Paper | Regular issue | Vol 57, No. 1, 2002, pp. 97 - 110
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DOI: 10.3987/COM-01-9371
Preparation of Thieno[2,3-b]pyrazines as Bioisosteres for Quinoxaline Derivatives wiht Reverse Transcriptase Inhibition

Thomas Erker* and Karin Trinkl

*Institute of Pharmaceutical Chemistry, University of Vienna, Pharmaziezentrum, Althanstrsse 14, A-1090 Vienna, Austria


Replacement of the fused aromatic moiety in GW-420867X, a HIV-1 specific nonnucleoside reverse transcriptase inhibitor, with thiophene provided 2-oxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine derivatives. The synthesis starts with the reaction of 5-acyl-2-chloro-3-nitrothiophene and different amino acid derivatives. The resulting substitution products are reduced, cyclized and N-acylated to give the desired compounds (27 - 33).

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Paper | Regular issue | Vol 57, No. 1, 2002, pp. 111 - 122
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DOI: 10.3987/COM-01-9375
Synthetic Studies on Thiostrepton Family of Peptide Antibiotics: Synthesis of the Tetrasubstituted Dihydroquinoline Portion of Siomycin D1

Syuhei Higashibayashi, Tomonori Mori, Kazuyuki Shinko, Kimiko Hashimoto,* and Masaya Nakata

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan


The tetrasubstituted dihydroquinoline portion of siomycin D1, a member of the thiostrepton family of peptide antibiotics, was synthesized from 5,6,7,8-tetrahydroquinoline featuring the modified Reissert-Henze reaction, the homolytic aromatic substitution reaction, the modified Boekelheide rearrangement, and the Jacobsen asymmetric epoxidation.

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Note | Regular issue | Vol 57, No. 1, 2002, pp. 123 - 128
Published online:
DOI: 10.3987/COM-01-9366
Acetylated Dimethoxyaniline as a Key Intermediate for the Synthesis of Aminoflavones and Quinolones

Nabajyoti Deka, Mohamed Hadjeri, Martin Lawson, Chantal Beney, and Ahcène Boumendjel*

*Laboratoire de Pharmacognosie, Département de Pharamcognosie Moleculaire, UMR-CNRS 5063, UFR de Pharmacie de Grenoble, 38706 La Tronche, France


3,5-Dimethoxyaniline was acetylated and found to be a key intermediate for the synthesis of a variety of biologically active aminoflavones and quinolones.

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Note | Regular issue | Vol 57, No. 1, 2002, pp. 129 - 133
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DOI: 10.3987/COM-01-9373
A New Ring-Forming Methodology for the Synthesis of Bioactive Pyrroloquinoline Derivatives

Margarita Vlachou, Andrew Tsotinis,* Lloyd R. Kelland, and David E. Thurston

*Department of Pharmaceutical Chemistry, School of Pharmacy, University of Athens, Panepistimiopolis-Zografou, Athens GR-15771, Greece


A new, efficient, two-step method for the synthesis of bioactive pyrroloquinolines is described. Readily available nitroquinolines, bearing the nitro moiety in the carbocyclic ring, are treated with 4-chlorophenoxyacetonitrile in the presence of potassium tert-butoxide/THF to give the analogous vicarious nucleophilic substitution products (5, 8 and 11). These, in turn, are subjected to catalytic hydrogenation to produce 1H-pyrrolo[2,3-f]quinoline (6), 3H-pyrrolo[3,2-f]quinoline (9) and 1H-pyrrolo[3,2-h]quinoline (12) in good yields and relatively short reaction times. The differential activity of two N-alkylated 1H-pyrrolo[2,3-f]quinolines (1) in cisplatin resistant cell lines compared to the corresponding parent lines suggests that these might be useful leads for developing agents for use in drug resistant diseases.

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Note | Regular issue | Vol 57, No. 1, 2002, pp. 135 - 142
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DOI: 10.3987/COM-01-9378
Formation of a New Polycyclic Heteroring System by the Acid-catalyzed Rearrangement of Thebaine in the Presence of Thiosalicylic Acid

Sándor Berényi,* Miklós Tóth, Susanna Gyulai, and László Szilágyi

*Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O.Box 20, Hungary


The methanesulfonic acid-catalyzed rearrangement of thebaine (1) in the presence of thiophenol resulted in 2-phenylthioapocodeine (7), whose O-demethylation gave 2-phenylthioapomorphine (8). An analogous transformation of 1 with thiosalicylic acid furnished the ethers (6) and (11) together with a polycyclic ketone (12) and a polycyclic acetal (15). Upon treatment of the acetal (15) with acid the thioxanthylium salt (16) was prepared.

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Note | Regular issue | Vol 57, No. 1, 2002, pp. 143 - 149
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DOI: 10.3987/COM-01-9384
Silver Ion-mediated Desulfurization-Condensation of Thiocarbonyl Compounds

Isao Shibuya,* Yasuo Gama, Masao Shimizu, and Midori Goto

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


The title reaction of N-hydroxybenzamide with aryl isothiocyanates at ambient temperature gave 5-(arylimino)-3-phenyl-1,4,2-dioxazoles (1, 2) with elimination of Ag2S. The structure of 1 was determined by X-Ray crystal structure analysis. N-Hydroxybenzamide also reacted with diaryl thioketones to afford condensation products, 5,5-diaryl-3-phenyl-1,4,2-dioxazoles(3, 4). Desulfurizations of diaryl thioketones with α-hydroxy acids and with salicylic acid gave in the same way 2,2-diaryl-5-phenyl-1,3-dioxolan-4-ones (5-8) and 2,2-diaryl-1,3-benzodioxan-4-ones (9-11), respectively. N-Phenylglycine and N-methylanthranilic acid gave similar types of condensation products (12, 13).

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Note | Regular issue | Vol 57, No. 1, 2002, pp. 151 - 155
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DOI: 10.3987/COM-01-9387
New Guaiane-Type Sesquiterpene Lactones from Hemisteptia lyrata Bunge

Tae Joung Ha, Min Suk Yang, Yunbae Pak, Jong Rok Lee, Kyung Dong Lee, Hwan Mook Kim, and Ki Hun Park*

*Department of Agricultural Chemistry , Division of Applied Life Science, Gyeongsang National University, Chinju, 660-701, Korea


Two new guaiane-type sesquiterpene lactones (1) and (2) together with 8-hydroxyzaluzanin C (3) were isolated from the flower of Hemisteptia lyrata. Compounds (1-3) were examined for their cytotoxic activity against LOX-IMVI, MCF-7, PC-3 and HCT-15 human cell line.

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Review | Regular issue | Vol 57, No. 1, 2002, pp. 157 - 167
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DOI: 10.3987/REV-01-543
Biologically Active Substances from Mushrooms in Yunnan, China

Liu Jikai

*Natural Products Chemistry, Kunming Institute of Botany, The Chinese Academy of Sciences, Kunming, 650204, China


As a part of our search for naturally occurring bioactive metablites of mushrooms, we investigated the chemical constituents of eight Basidiomycetes and Ascomycetes fungi (Albatrellus confluens, Russula lepida, Thelephora ganbajun, Russula cyanoxantha, Polyporus ellisii, Tuber indicum, Engleromyces gotzii, Tremella aurantilba, Laetiporus sulphureus and Tylopilus plumbeoviolaceus), and isolated a number of novel terpenoids, phenolics and nitrogen-containing compounds. The isolation, structural elucidation and biologically activity of the new compounds are discussed.

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Review | Regular issue | Vol 57, No. 1, 2002, pp. 169 - 185
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DOI: 10.3987/REV-01-544
Calixpyrroles and Related Compounds

Wanda Sliwa

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


The chemistry of calixpyrroles and related compounds is reviewed. Calixpyrroles, including examples of expanded species are presented along with calixphyrins. Synthetic approaches, binding properties and application possibilities of the above compounds are dedescribed.

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18 data found. 1 - 18 listed