Regular Issue

Vol. 45, No. 4, 1997

21 data found. 1 - 21 listed
Communication | Regular issue | Vol 45, No. 4, 1997, pp. 643 - 650
Published online:
DOI: 10.3987/COM-97-7750
Facile and General Syntheses of 1-Alkyltoxoflavin and 8-Alkylfervenulin Derivatives of Biological Significance by the Regiospecific Alkylation of Reumycin (1-Demethyltoxoflavin, 8-Demethylfervenulin) Derivatives

Tomohisa Nagamatsu* and Hirofumi Yamasaki

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


Regiospecific alkylation of reumycins (6) under alkaline conditions with a dialkyl sulfate or alkyl halide in dioxane and in DMF to provide 1-alkyltoxoflavins (5) of biological significance and 8-alkylfervenulins (7), respectively, is described.

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Communication | Regular issue | Vol 45, No. 4, 1997, pp. 651 - 658
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DOI: 10.3987/COM-97-7754
Syntheses and Structural Properties of Severely Distorted Porphyrins: N-Methyl Derivatives

Todd E. Clement, Liem T. Nguyen, Richard G. Khoury, Daniel J. Nurco, and Kevin M. Smith*

*Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616-5295, U.S.A.


Syntheses and characterization of a series of N-methylated derivatives of sterically distorted porphyrins are reported; the work includes the first example of a tetra-N-methylated porphyrin obtained by methylation of an intact porphyrin.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 659 - 672
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DOI: 10.3987/COM-96-7644
Chemistry of Denudatine V. Rearrangement Reactions of Denudatine

Feng-Peng Wang,* Jian-Zhong Wang, and Rong Zhang

*Department of Chemistry of Medicinal Natural Products, School of Pharmacy, west China University of Medical Sciences, Chengdu 610041, China


Treatment of denudatine 1 with 10% HCl solution at 30-50 °C leads to rearrangement to two pairs of epimers (5A) and (5B), (8A) and (8B) as well as 7 and 15. The rearrangement mechanisms are discussed. Conversion of 75A/5B15 under acid catalysis can be realized. While the conversion of 15 to 5A/5B, can be realized with NaOH-DMF at 120-126 °C. Structures for 5A/5B, 7, 8A/8B and 15 were established on the basis of chemical and spectral methods.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 673 - 682
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DOI: 10.3987/COM-96-7678
Pyridazines, 81. A Novel 1,2-Diazine Containing Tricyclic System: Synthesis of Pyridazino[3,4-b][1,5]benzodiazepin-5-ones as Potential HIV-1 Reverse Transcriptase Inhibitors

Gottfried Heinisch, Barbara Matuszczak,* and Kurt Mereiter

*Institute of Pharmaceutical Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria


Ring closure reactions of 3-alkylamino-6-chloro-N-phenylpyridazine-4-carboxamides (7, 10, 13) bearing a halogen function in ortho position of the carbocyclic moiety were shown to provide convenient access to the pyridazino[3,4-b][1,5]benzodiazepin-5-one system.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 683 - 690
Published online:
DOI: 10.3987/COM-96-7704
Synthesis of 3-(4-Methoxyphenyl)-5,7-dimethoxy-(1H)-qunolin-2- or 4-ones and Derivatives

Martine Croisy, Christiane Huel, and Emile Bisagni

*UMR 176 CNRS, Institut Curie, Section de Recherche, Bâtiments 110-112, Centre Universitaire, 91405 Orsay Cedex, France


Condensation of ethyl 2-(4-methoxyphenyl)-3-hydroxyacrylate with 3,5-dimethoxyaniline afforded, depending on experimental conditions, either 3-(4-methoxyphenyl)-5,7-dimethoxy-(1H)-quinolin-2-one or 3-(4-methoxyphenyl)-5,7-dimethoxy-(1H)-quinolin-4-one. Whereas chlorination with phosphorous oxychloride led to the corresponding 2- and 4-chloroquinolines derivatives, 2-chloro-3-(4-methoxyphenyl)-5,7-dimethoxyquinoline was also obtained by using the Meth Cohn method’s.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 691 - 700
Published online:
DOI: 10.3987/COM-96-7715
Direct Synthetic Approach to N-Substituted 1-Amino-2,3-dihydro-1H-imidazole-2-thiones

Joachim G. Schantl* and Irene M. Lagoja

*Institut für Organische Chemie, Universität Innsbruck, Innrain 52, A-6020 Innsbruck, Austria


In a efficient one-pot procedure, the title compounds (8) were obtained by the reaction of α-halo ketones (1) with potassium thiocyanate and monosubstituted hydrazines (3). The reaction is considered to proceed via the formation of azo-alkenes (5) and thiocyanic acid. These intermediates, in turn, undergo a [3+2] cycloaddition reaction; the resultant azomethine imine cycloadducts (6) are transformed into the final products (8). The structure of compounds (8) has been confirmed by utilization of various NMR techniques.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 701 - 706
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DOI: 10.3987/COM-96-7720
Total Synthesis of Polyhydroxylated Piperidine and Pyrrolidine : Expect as Glucosidase Inhibitor

Sang Gyeong Lee,* Yong-Jin Yoon, Sung Chul Shin, Bu Yong Lee, Su-Dong Cho, Sung Kyu Kim, and Ji-Hyun Lee

*Department of Chemistry, Research Institute of Natural Science, Gyeongsang National University, Chinju, 660-701, Korea


A new method for preparation of optically active (-)-deoxymannojirimycin (3) and 2R,5S-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (13) based on regioselective epoxide ring opening of 2-tert-butoxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5,6-epoxy-D-glucitol (12) by intramolecular nucleophilic amination has been described.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 707 - 713
Published online:
DOI: 10.3987/COM-96-7730
One-Pot Synthesis of 1,10-Dihydro-2H-imidazo[3,4-a]quinazolin-1-ones from 3-Acyl-1,2-dihydrocinnoline-1,2-dicarboximides

Kazuyoshi Seguchi* and Satoko Tanaka

*Faculty of Human Environmental Sciences, Mukogawa-Women's University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan


3-Substituted 1,10-dihydro-2H-imidazo[3,4-a]quinazolin-1-ones were prepared from 3-acyl-1,2-dihydrocinnoline-1,2-dicarboximides and piperidine in DMSO in moderate yields via Michael additions, skeletal rearrangements, and subsequent decarboxylation.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 715 - 722
Published online:
DOI: 10.3987/COM-96-7731
Remarkable Fast N-Alkylation of Azaheterocycles under Microwave Irradiation in Dry Media

Dariusz Bogdal,* Jan Pielichowski, and Krzysztof Jaskot

*Institute of Organic Chemistry, Politechnika Krakowska, ul. Warszawska 24, 31-155 Krakowska, Poland


Under microwave irradiation a number of azaheterocycles (i.e., pyrrole, imidazole, pyrazole, indole, and carbazole) react remarkably fast with alkyl halides to give exclusively N-alkyl derivatives.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 723 - 734
Published online:
DOI: 10.3987/COM-97-7736
Synthesis of 1-[ω-[(Arylamino)carbonyl]-alkyl]-4-(benzocycloalkyl)piperazines

Youssef El-Ahmad, Philippe Maillet, Elisabeth Laurent, Akram Talab, Gilles Tran, and Roland Ollivier*

*Centre de Recherche, Coorpération Pharmaceutique Française, 13, rue Benjamin Franklin, 77000 La Rochette, France


A series of 1-[ω-[(arylamino)carbonyl]alkyl]-4-(benzocycloalkyl)piperazines (1a-v) was prepared either by reacting the precursor 4-[ω-[(arylamino)carbonyl]alkyl]piperazine (2a-j) with 1-chlorobenzocycloalkanes (3a-c) (Procedure A) or by reacting the N-aryl-ω-chloroalkanamides (5a-j) with the 4-(benzocycloalkyl)piperazines (10a-c) (Procedure B). The best yields were obtained using procedure A.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 735 - 744
Published online:
DOI: 10.3987/COM-97-7739
Reactivity of 1,3-Di-tert-butylaziri-dinones with Phenyl Substituents. A New Fragmentation of α-Lactams

Masako Shimazu, Yasuyuki Endo,* and Koichi Shudo

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan


Several isolable aziridinones with bulky substituents were prepared and their reactions with nucleophiles, i.e., methanol, sodium methoxide and benzylamine, were investigated. A novel fragmentation of aziridinones having a phenyl group on the C3 moiety was found.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 745 - 755
Published online:
DOI: 10.3987/COM-97-7740
Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide

Akira Miyashita,* Izuru Nagasaki, Akiko Kawano, Yumiko Suzuki, Ken-ichi Iwamoto, and Takeo Higashino

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


Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 757 - 763
Published online:
DOI: 10.3987/COM-97-7745
Novel Entry into Benzo[c]phenanthridine Systems through a Tandem Alkene Acylation-Cyclodehydration

Raul SanMartín, Eduardo Martínez de Marigorta, Isabel Moreno, and Esther Domínguez*

*Kimika Organikoa Saila, Zientzi Fakultatea, Euskal Herriko Unibertsitatea, Vasco, P.O. Box 644, 48080-Bilbao, Basque Country, Spain


12-alkylbenzo[c]phenanthridines have been obtained by an overall high yielding synthetic methodology. Key steps involve Peterson methylenation and an efficient one-pot alkene acylation-cyclization. Smooth oxidation to the benzo[c]phenanthridinone system is also reported.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 765 - 772
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DOI: 10.3987/COM-97-7748
Arylation of 1,3-Dimethyllumazines by Arenediazonium Salts

Takashi Sugimoto* and Wolfgang Pfleiderer

*Department of Natural Science Informatics, School of Informatics and Sciences, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


Reaction of 7-methoxy-1,3-dimethyllumazine with benzenediazonium chloride in an alkaline aqueous solution afforded 6-phenyl- and 6-biphenyl-7-methoxy-1,3-dimethyllumazines. Treatment of 7-dimethylamino-1,3-dimethylluamzine with benzenediazonium chloride similarly gave the 6-phenyl and 6-biphenyl derivatives of the substrate together with 7-methylamino-6-phenyl-1,3-dimethyllumazine. Analogous reactions of 7-substituted 1,3-dimethyllumazines with several arenediazonium chlorides are described.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 773 - 778
Published online:
DOI: 10.3987/COM-97-7749
New Ring Transformation Reaction of Imidazothiazole with Acetylenic Acid Esters

Dong Chan Kim, Dong Jin Kim, Kye Jung Shin, Sang Woo Park*, and Kyung Ho Yoo*

*Biochemicals Research Center, Division of Applied Science, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea


3-Phenyl-5,6-dihydroimidazo[2,1-b]thiazole (1) as a nucleophile reacted with acetylenic acid esters such as ethyl propiolate and dimethyl acetylenedicarboxylate to give the new ring transformation compounds (2-oxo-imidazoline-1-yl)acrylic acid ethyl esters (6a-b) and [2-oxo-imidazoline-1-yl]but-2-enedioic acid diethyl esters (7a-b), respectively. Similarly, treatment of reactive imidazo[2,1-b]thiazolium betaines (3a-b) with acetylenic acid derivatives led to the corresponding ring transformation compounds. This reaction proceeded by the participation of water, and the resulting compounds were obtained in a mixture of cis and trans isomers.

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Paper | Regular issue | Vol 45, No. 4, 1997, pp. 779 - 786
Published online:
DOI: 10.3987/COM-97-7752
Synthesis of (±)-Cathenamine and (±)-19-Epicathenamine, Isolated as Their C-21α-Cyano Derivatives

Mauri Lounasmaa,* Reija Jokela, Pirjo Hanhinen, and Ulla Anttila

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland


A short synthetic route from the easily accessible O-Boc-Z-geissoschizine (2a) to (±)-cathenamine (3) and (±)-19-epicathenamine (4) is presented. Both compounds, which are important biogenetic intermediates in the formation of heteroyohimbine alkaloids, were isolated as their synthetic equivalents, (±)-21α-cyanotetrahydroalstonine (5) and (±)-21α-cyano-19-epiajmalicine (6), respectively.

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Note | Regular issue | Vol 45, No. 4, 1997, pp. 787 - 794
Published online:
DOI: 10.3987/COM-96-7660
Heterocycles from 2-Aminopyridine and Derivatives of 3-Methylbenzofuran-2-carboxylic Acid

Yvette A. Jackson* and Mark F. Williams

*Department of Chemistry, Mona Campus, University of the West Indies, Mona, Kingston 7, Jamaica, West Indies


3-Bromoethyl-2-carboethoxy-5,6-dimethoxybenzofuran (3b) reacted with 2-aminopyridine to give not only the expected 2-carboethoxy-5,6-dimethoxy-3-benzofuranmethyl-2’-aminopyridinium bromide (4b), but also N-(2-carboethoxy-5,6-dimethoxy-3-benzofuranmethyl)-N-2-pyridylamine (5). Synthesis of 3-methoxy-6,7,12-trihydro-6-oxo-[1]benzofurano[2,3-c]-1H-pyrido[1,2-a][1,3]diazepinium bromide (12) is also described.

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Note | Regular issue | Vol 45, No. 4, 1997, pp. 795 - 803
Published online:
DOI: 10.3987/COM-96-7684
One Pot Synthesis of Selenides Containing Polyarylthioether Moiety

Song Seok Shin and Kyongtae Kim*

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


The reactions of 5-arylthianthreniumyl perchlorates with sodium hydrogen selenide in ethanol and lithium n-butylselenolate in tetrahydrofuran under nitrogen at reflux afforde bis[2-(2-arylthiophenylthio)phenyl] selenides and 2-arylthio-2’-(n-butylseeleno)diphenyl sulfides in 26 - 83% and 23 - 98% yields, respectively. A sulfurane mechanism is proposed.

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Note | Regular issue | Vol 45, No. 4, 1997, pp. 805 - 810
Published online:
DOI: 10.3987/COM-96-7716
AICI3-DMF Reagent in the Friedel-Crafts Reaction. Application to the Synthesis of Symmetrical Benzophenones Derivatives

Huseyin Ucar,* Kim Van derpoorten, and Jacques H. Poupaert

*Unité de Chimie Pharmaceutique, Ecole de Pharmacie, Université Catholique de Louvain, Avenue E. Mounier 73, B-1200 Bruxelles, Belgium


Synthesis of series of symmetrical benzophenone derivatives by C-alkylation reaction of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone with carbon tetrachloride in presence of AlCl3-DMF reagent is reported.

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Note | Regular issue | Vol 45, No. 4, 1997, pp. 811 - 816
Published online:
DOI: 10.3987/COM-96-7729
Reaction of Pyridine-N-oxide with a Strained Seven-membered Cycloalkyne. A Correction

Hans Jörg Lindner, Adolf Krebs,* Jan-Hinrich Förster, and Volker Sinnwell

*Institut für Organische Chemie, Universitat Hamburg, Martin-Luther-King-Platz 6, D-20416 Hamburg, Germany


Pyridine-N-oxide adds at room temperature to 3,3,6,6-tetramethyl-1-thia-cycloheptyne to give the 3H-azepine (3). A mechanism of formation for 3 is discussed. On heating 3 rearranges to yield the 3-substituted pyridine (8).

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Note | Regular issue | Vol 45, No. 4, 1997, pp. 817 - 821
Published online:
DOI: 10.3987/COM-97-7756
Fumaflorine, a New 1-Benzylisoquinoline Alkaloid from Fumaria densiflora

Eva Táborská, Hana Bochoráková, Jaromír Sousek, Petr Sedmera, Vladimír Havlícek, and Vilím Simánek*

*Institute of Medical Chemistry, Palacky University, 3, Hnevotínská, 775 15 Olomouc, Czech Republic


Fumaflorine (1), a new 1-benzylisoquinoline alkaloid, was isolated from the aerial parts of Fumaria densifloira. Its structure was determined by spectroscopic methods.

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21 data found. 1 - 21 listed