Regular Issue

Vol. 60, No. 11, 2003

17 data found. 1 - 17 listed
Contents | Regular issue | Vol 60, No. 11, 2003
Published online:
DOI: 10.3987/Contents-03-6011
Communication | Regular issue | Vol 60, No. 11, 2003, pp. 2417 - 2424
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9833
Synthesis of Furazane Conjugated New Heterocycles

Renaud Beaudegnies* and Sebastian Wendeborn

*Syngenta Crop Protection AG, Optimization Chemistry, CH-4002 Basel, Switzerland


An improved route for the synthesis of 3-(4-aminofurazane-3-yl)-1,2,4-oxadiazole heterocycles using micro-wave irradiation is reported. The preparation of novel 4-(thiazol-4-yl)furazan-3-ylamine, 4-(pyrimidin-4-yl)furazan-3-ylamine and, 4-(pyrazolidin-3-yl)furazan-3-ylamine heterocycles are described.

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Communication | Regular issue | Vol 60, No. 11, 2003, pp. 2425 - 2428
Published online: 5th September, 2003
DOI: 10.3987/COM-03-9861
Hydrothermolysis of the Fully Benzylated α-Cyclodextrin

Takashi Yamanoi,* Naoshi Inoue, Masaki Fujimoto, Hideaki Sasaura, and Akihiko Murota*

*The Noguchi Institute, 1-8-1, Kaga, Itabashi-ku, Tokyo 173-0003, Japan


The treatment of the fully benzylated α-cyclodextrin with the hot compressed mixed solvent of dioxane/water (v/v=1/1) at 270 °C and 150 kg/cm2 for 40 min afforded 2,3,6-tri-O-benzyl-D-glucopyranose in good yield. The hydrothermolysis of the fully benzylated α-cyclodextrin at 240 °C produced partially benzylated maltooligosaccharide derivatives.

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Communication | Regular issue | Vol 60, No. 11, 2003, pp. 2429 - 2434
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9883
Concise Synthesis of Pyrrolophenanthridine Alkaloids Using a Pd-Catalyzed Biaryl Coupling Reaction with Regioselective C-H Activation

Takashi Harayama,* Akihiro Hori, Hitoshi Abe, and Yasuo Takeuchi

*Faculty of Pharmaceutical Science, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


The concise synthesis of the pyrrolophenanthridine alkaloids such as anhydrolycorine, assoanine, anhydrolycorin-7-one, and oxoassoanine, was achieved using the Pd-catalyzed biaryl coupling reaction of 1-(2-halobenzyl)-2,3-dihydroindole by applying the regioselective C-H activation method with intramolecular coordination of the benzylamino group to Pd.

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2435 - 2440
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9837
Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones over Silica Sulfuric Acid as a Reusable Catalyst under Solvent-free Conditions

Peyman Salehi,* Minoo Dabiri, Mohammad Ali Zolfigol, and Mohammad Ali Bodaghi Fard

*Department of Phytochemistry, Aromatic and Medicinal Plants and Drug Research Institute, Shahid Beheshti University, Evin, Tehran 19835-389, Iran


3,4-Dihydropyrimidin-2(1H)-ones and their sulfur analogues are efficiently synthesized by the three-component condensation of β-dicarbonyl compounds, aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amounts of silica sulfuric acid under solvent-free conditions in high yields. The catalyst is recyclable and can be used several times without any decrease in the products yields.

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2441 - 2455
Published online: 8th September, 2003
DOI: 10.3987/COM-03-9838
Synthesis of 5-Substituted Indole Derivatives. Part 4: Naratriptan from α-Anilinoacetaldehyde Dimethylacetal by TiCl4-Mediated Cyclisation

Béla Pete,* Gyula Simig, László Poszávácz, and László Toke

*Research Group of the Hungarian Academy of Sciences, Department of Organic Chemical Technology, Technical University of Budapest, H-1521 Budapest, Hungary


N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (Naratriptan, 2) was prepared from N-methyl-N-phenylmethyl-2-(4-aminophenyl)-ethanesulfonamide (3b) through reductive alkylation with dimethoxyacetaldehyde followed by N-acylation and TiCl4-mediated indolisation, according to Sundberg procedure. The isopropyl group proved to be a useful protecting group for sulfonate esters in a number of transformations but was cleaved in the presence of TiCl4.

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2457 - 2470
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9842
Highly Fluorescent Heterocycles Based on Pyrazino Fused 1,4,5,8-Tetraazafulvalenes

Christian Käpplinger, Rainer Beckert,* Jan Koci, Gabriela Braunerova, Karel Waisser, and Helmar Görls

*Institute for Organic and Macromolecular Chemistry, Friedrich Schiller University, Lessingstr. 8, D-07743 Jena, Germany


Some new pyrazino-fused 1,4,5,8-tetraazafulvalenes of type (3-5) were synthesized and their structures were confirmed by IR, UV-VIS, 1H NMR spectra and elemental analysis. The X-Ray crystal structure analysis of a single crystal of derivative (3c) revealed a nearly ideal planarized heterofulvalene subunit. The new prepared tricyclic tetraazafulvalenes of type (3) show strong red fluorescence at 605 nm.

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2471 - 2483
Published online: 5th September, 2003
DOI: 10.3987/COM-03-9850
5-Alkynyl-4-chloro- and 4-Alkynyl-5-chloro-2-methylpyridazin-3(2H)-ones: Convenient Precursors for the Preparation of 2-Substituted Pyrrolo[2,3-d]pyridazinones

Omar R’kyek, Bert U. W. Maes, Guy L. F. Lemière,* and Roger A. Dommisse

*Department of Chemistry, University of Antwerp (RUCA), Groenenborgerlaan 171, B-2020 Antwerp, Belgium


A new synthetic route towards the synthesis of 1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-ones (10a-f) and their regioisomers 1,5-dihydro-4H-pyrrolo[2,3-d]pyridazin-4-ones (9a,b) is described, based on the reaction of 5-alkynyl-4-chloro- (7a,b) and 4-alkynyl-5-chloropyridazinones (8) with different amines (ammonia, methylamine and propylamine) followed by a treatment with a NaOEt solution.

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2485 - 2498
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9854
A Stereoselective Approach to Both 3,4-trans-Disubstituted Pyrrolidin-2-ones and Pyrrolidines. A Convenient Synthesis of (3R,4R)-4-Benzyl-3-pyrrolidinecarboxylic Acid

Roberta Galeazzi, Gianluca Martelli, Giovanna Mobbili, Mario Orena,* and Maria Panagiotaki

*Dipartimento di Scienze dei Materiali e della Terra - Università Politecnica delle Marche, Via Brecce Bianche, I-60131 Ancona, Italy


Chiral 4-alkyloxymethyl- and silyloxymethylpyrrolidin-2-ones, (10a-c), underwent alkylation to give the corresponding 3,4-trans-disubstituted pyrrolidin-2-ones, (11a-g), in good yield and total stereoselection, as shown by 1H NMR spectral data and n.O.e. experiments. Moreover compounds (11a-c) were converted into the corresponding 3,4-trans-disubstituted pyrrolidines, (12a-c). Removal of the chiral auxiliary from 12a, followed by protection of the nitrogen with t-Boc group, led to the corresponding derivative (13). Cleavage of the benzyl ether and subsequent oxidation of the hydroxy function afforded (3R,4R)-4-benzyl-3-pyrrolidinecarboxylic acid (4).

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2499 - 2510
Published online: 5th September, 2003
DOI: 10.3987/COM-03-9869
Synthesis of Multi-substituted Pyrazoles Utilizing the N-Alkylated 3-Hydroxy-3-propargyl- or Allenylisoindolines

Yong Hyun Choi, Kyung Soon Kim, Sangku Lee, Tae-Sook Jeong, Hee-Yoon Lee, Yong Hae Kim, and Woo Song Lee*

*Korea Research Institute of Bioscience and Biotechnology, 52 Oun, Yusong, Daejeon 305-333, Korea


N-Alkyl-substituted phthalimides (1) were easily converted to di-, tri-, and tetra-substituted pyrazoles (10) via a one-pot addition-decyclization-cyclocondensation process. Then, the structure and the position of N1-substitution of the 1,3-pyrazole ring were determined by X-Ray crystallographic analysis and 1H-nOe experiments.

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2511 - 2517
Published online: 5th September, 2003
DOI: 10.3987/COM-03-9872
Synthesis of the Tetrahydropteridine-2,4-dione Having a Substituted Methyl Group at 6-Position

Masaru Tada,* Tomoyuki Shimamura, and Takeaki Suzuki

*Department of Chemistry, School of Science and Engineering, Waseda University, Shinjuku-ku, Tokyo 169-8555, Japan


Lewis acid treatment of 5-amino-6-(N-2,3-epoxypropyl-N-tosyl)amino-1,3-dimethyluracil (3) gave the diazepine (4) fused to uracil ring, and the tosylate (5) from 4 underwent ring transformation to provide tetrahydropteridinediones (7 and 8) depending on the reaction conditions. Thus, heating in dry acetonitrile led to 6-tosyloxymethyltetrahydropteridine-2,4-dione (7) whereas that in wet acetonitrile to 6-hydroxymethyl derivative (8).

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Paper | Regular issue | Vol 60, No. 11, 2003, pp. 2519 - 2525
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9876
Synthesis of 8,9,10,11-Tetrahydroindolo[2,1-c]benzo[1,2,4]triazine. A New Ring Syntem

Paola Barraja, Patrizia Diana, Antonino Lauria, Alessandra Montalbano, Anna Maria Almerico, Gaetano Dattolo, and Girolamo Cirrincione*

*Dipartimento Farmacochimico Tossicologico e Biologico Università degli Studi di Palermo Via Archirafi 32, 90123 Palermo, Italy


Indolo[2,1-c]benzo[1,2,4]triazine, a new ring system, was synthesized by diazotization of 2-amino-1 aryltetrahydroindoles followed by an intramolecular coupling of the diazonium group with the aryl moiety. All the new compounds were screened at the NCI for antiproliferative property but none of them showed significant activity.

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Note | Regular issue | Vol 60, No. 11, 2003, pp. 2527 - 2534
Published online: 5th September, 2003
DOI: 10.3987/COM-03-9864
Synthesis and Crystal Structure of 2’,4”-O-Bis(trimethylsilyl)erythromycin A 9-O-(1-Isopropoxycyclohexyl) Oxime

Jian-Hua Liang and Guo-Wei Yao*

*School of Life Science and Technology, Beijing Institute of Technology, Beijing 100081, China


The ratio of E/Z of 2’-,4”-O-bis(trimethylsilyl)erythromycin A 9-O-(1-isopropoxycyclohexyl) oxime were much higher prepared in CH3CN than those in CH2Cl2. And the ratio would increase with elevation of temperature. Compared with 2’-OH, 4”-OH was liable to be silylated in the presence of 1,1,1,3,3,3-hexamethyldisilizane and an NH4+. The crystal structure of E-title compound was determined by single-crystal X-Ray structure analysis to elucidate the origin of regioselectivity occurring at 6-hydroxyl group in the O-methylation of erythromycin A.

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Note | Regular issue | Vol 60, No. 11, 2003, pp. 2535 - 2542
Published online: 5th September, 2003
DOI: 10.3987/COM-03-9866
Synthesis and Characterization of a New Metal-free Azaphthalocyanine Containing Four Peripheral Ion Jacks

Xiguang Du,* Chunyu Ma, Xiaoke Hou, Gui Wang, Wancheng Li, and Guotong Du*

*Laboratory of Organic Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, China


A synthesis of a new 1,10-phenanthroline-appended metal-free azaphthalocyanine(azaPc), which is generated from precursor, 10,12-diimino-11 H-pyrrolo[3,4-b]dipyrido[3,2-f:2’,3’-h]quinoxaline, is described. This azaPc is purified by absolute methanol in a Soxlet apparatus, then under high vacuum (10-4Pa) and is unequivocally characterized by its elemental analysis and spectrometry.

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Note | Regular issue | Vol 60, No. 11, 2003, pp. 2543 - 2549
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9871
Reactions of 9-Phosphorylacridines with Aqueous Hydrogen Peroxide Accompanied by Weak Chemiluminescence: Remarkable Substituent Effect on Emission Efficiency

Jiro Motoyoshiya,* Rie Shima, Yutaka Takaguchi, Yoshinori Nishii, and Hiromu Aoyama

*Department of Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano 386-8567, Japan


The reaction of 9-phosphorylacridines with aqueous hydrogen peroxide provides weak chemiluminescence, whose emission efficiency depends on the structures of the phosphorus groups. The bulky substituents in the phosphorus groups increased the chemiluminescence quantum yields, which can be explained by assuming that the present chemiluminescence reaction involves a CIEEL process via phospha-1,2-dioxetanes as the high-energy intermediates.

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Note | Regular issue | Vol 60, No. 11, 2003, pp. 2551 - 2556
Published online: 5th September, 2003
DOI: 10.3987/COM-03-9874
Synthesis of Novel Chiral Spiro Bis(pyrazole) Ligands

Shinobu Takizawa, Yuji Honda, Midori A. Arai, Takahiro Kato, and Hiroaki Sasai*

*The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan


The first synthesis of spiro bis(pyrazole) ligands, 2,2’,4,4’-tetrahydro-6,6’-spirobi[5H-cycopentapyrazole] (1a) and 2,2’-dibenzyl-2,2’,4,4’-tetrahydro-6,6’-spirobi[5H-cycopentapyrazole] (1b) was achieved. The application of spiro bis(pyrazole) ligand to asymmetric catalysis was also examined.

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Note | Regular issue | Vol 60, No. 11, 2003, pp. 2557 - 2563
Published online: 16th September, 2003
DOI: 10.3987/COM-03-9882
Flavonol Glycosides in Two Diospyros Plants and Their Radical Scavenging Activity

Miyuki Furusawa, Tetsuro Ito, Ken-ichi Nakaya, Toshiyuki Tanaka,* Iliya Ibrahim, Munekazu Iinuma, Hiroko Murata, Yuka Inatomi, and Tsutomu Nakanishi

*Gifu Prefectrual Institute of Health and Environmental Sciences, 1-1 Nakafudogaoka, Kakamigahara, Gifu 504-0838, Japan


Methanol extracts of leaves of Diospyros glaucifolia and D. kaki were showed the scavenging activity of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. Chromatographical separation and purification of methanol extracts resulted in isolation of three new flavonol glycosides [2”-(E)-p-coumaroylmyricitrin (3), 3”-(E)-p-coumaroylmyricitrin (4) and mearsetin 3-O-β-glucronopyranoside (11)] along with known phenolic compounds. These structures were determined by means of spectroscopic analysis. The scavenging activities of DPPH radical of the isolated compounds were examined.

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17 data found. 1 - 17 listed