Regular Issue

Vol. 68, No. 4, 2006

19 data found. 1 - 19 listed
Communication | Regular issue | Vol 68, No. 4, 2006, pp. 667 - 672
Published online: 14th March, 2006
DOI: 10.3987/COM-06-10680
Synthesis and Luminescent Properties of Bis(fluoren-9-ylidenemethyl)aromatics: Green and Red Materials in Organic Electroluminescent Devices

Katsuhiko Ono,* Takao Hiei, and Katsuhiro Saito

*Department of Life and Material Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Derivatives of 4,4’-bis(2,2-diphenylvinyl)biphenyl (DPVBi) were prepared and investigated for application in green and red fluorescent emitters in organic electroluminescent (EL) devices. Although the green emitter showed yellowish green electroluminescence, a series of π-conjugated compounds revealed the potential for a red-green-blue (RGB) fluorescent system.

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Communication | Regular issue | Vol 68, No. 4, 2006, pp. 673 - 677
Published online: 7th March, 2006
DOI: 10.3987/COM-06-10684
The Brφnsted Acid-catalyzed O-Glycosidation of 1-C-Alkyl-D-glucopyranose Derivatives

Takashi Yamanoi,* Sho Matsuda, Ippo Yamazaki, Ryo Inoue, Keita Hamasaki, and Mikio Watanabe

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


We found that the O-glycosidation between various kinds of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses and alcohols in the presence of 5 mol % of trifluoromethanesulfonic acid or bis(trifluoromethane)sulfonimide stereoselectively produced the corresponding 1-C-alkyl-α-D-glucopyranosides in good yields.

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Paper | Regular issue | Vol 68, No. 4, 2006, pp. 679 - 686
Published online: 3rd March, 2006
DOI: 10.3987/COM-05-10662
Synthesis of Chiral Thiazolo[3,4-a]pyrazine-5,8-diones

Teresa M. V. D. Pinho e Melo,* Susana M. M. Lopes, António M. d’A. Rocha Gonsalves, José A. Paixão, Ana Matos Beja, and Manuela Ramos Silva

*Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal


A synthetic approach to chiral (3R,8aR)-3-phenyltetrahydro- thiazolo[3,4-a]pyrazine-5,8-diones starting from a (2S,4R)- and (2R,4R)-diastereoisomeric mixture of 2-phenylthiazolidine is described. The diastereoselective N-acylation of the thiazolidine followed by condensation with amines affords the chiral 1,3-thiazolidine-annulated system. The structure of (3R,8aR)-7-(methoxycarbonylmethyl)-3-phenyltetrahydrothiazolo[3,4-a]pyrazine-5,8-dione was determined by X-Ray crystallography.

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Paper | Regular issue | Vol 68, No. 4, 2006, pp. 687 - 699
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-10666
Synthesis, Structure and Transformations of 2-Iminoimidazolidines into Novel Fused Heterocyclic Ring Systems

Anita Kornicka,* Franciszek Saczewski, and Maria Gdaniec

*Department of Chemical Technology and Drugs, Medical University of Gdansk, Al. Gen.J. Hallera 107, 80-416 Gdansk, Poland


Reaction of 2-chloro-4,5-dihydroimidazole (1) with 2-aminobenzylamines (2a-d) afforded 2-[(imidazolidin-2-ylideneamino)methyl]anilines (3a-d) which upon treatment with carbon disulfide gave 2,3-dihydro-12H-imidazo[2’,1’:4,5][1,3,5]thiadiazino[2,3-b]quinazolin-5-thiones (4a-d) and 3,4-dihydro-1H-quinazolin-2-thiones (5a-c). Analogous reaction of 1 with 2-aminobenzyl alcohol (6) led to the formation of [2-(4,5-dihydro-1H-imidazol-2-ylamino)phenyl]methanol hydrochloride (7) which was transformed into 1-(4H-3,1-benzoxazin-2-yl)imidazolidin-2-thione (8).

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Paper | Regular issue | Vol 68, No. 4, 2006, pp. 701 - 712
Published online: 10th March, 2006
DOI: 10.3987/COM-06-10667
1,3-Dibromo-5,5-dimethylhydantoin as a New Imidazolidine Dehydrogenating Agent: Synthesis of 4,5-Dihydro-1H-imidazolium Salts

María C. Caterina, María A. Figueroa, Isabel A. Perillo, and Alejandra Salerno*

*Department of Organic Chemistry, Faculty of Pharmacy and Biochemistry, University of Buenos Aires, Junín 956 (1113) Buenos Aires, Argentina


A study about the scope of the method for the attainment of 4,5-dihydro-1H-imidazolium salts by dehydrogenation of N,N’-dibenzyl- and N-aryl-N’-benzylimidazolidines is presented. Employed dehydrogenating agents were N-bromoacetamide (NBA), N-bromosuccinimide (NBS), carbon tetrachloride and 1,3-dibromo-5,5-dimethylhydantoin (DBDMH). DBDMH was the choice reagent due to the purity of the attained products, lowest reaction times and highest yields.

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Paper | Regular issue | Vol 68, No. 4, 2006, pp. 713 - 719
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-10670
New Synthesis of Naratriptan

László Poszávácz,* Gyula Simig, József Fetter, and Ferenc Bertha

*Chemical Research Deivision, EGIS Pharmaceuticals Ltd., P.O.Box 100, H-1475 Budapest, Hungary


A new synthesis of N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (naratriptan, 1a) has been elaborated starting from 1-benzyl-1H-indole-5-carbaldehyde (14b). The 1-benzyl group proved to be an advantageous protecting group in the course of the construction of the ethanesulfonamide and methylpipieridinyl side-chains and it was removed in the last step of the synthesis.

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Paper | Regular issue | Vol 68, No. 4, 2006, pp. 721 - 732
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-10675
Synthesis of Peptidomimetic Analogues of Echinocandins

Chao-Mei Ma, Sunao Takeda, Satoshi Hibino, and Mohsen Daneshtalab*

*School of Pharmacy, Memorial University of Newfoundland, St. John’s, NL, A1B 3V6, Canada


Novel peptidomimetic compounds with partial structures being the same as that of echinocandin B, a well known antifungal lipopeptide, have been synthesized. The structures of these compounds were confirmed by NMR and MS. The synthesized compounds were tested for their in vitro antifungal activity. The results suggested that the hydroxyproline-threonine section in the north-western position of the echinocadin is important for the activity.

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Paper | Regular issue | Vol 68, No. 4, 2006, pp. 733 - 748
Published online: 10th March, 2006
DOI: 10.3987/COM-06-10699
New Efficient Blue-greenish Electroluminescent Materials of 1,3,4-Oxadiazole-based Pyrazole Derivatives

En-Ming Chang, Chi-Jen Lin, Fung Fuh Wong,* and Mou-Yung Yeh*

*Sustainable Environment Research Center, National Cheng Kung University, No. 500, Sec. 3, An-ming Rod., Tainan City, 709, Taiwan, R.O.C.


Novel blue-greenish electroluminescent materials of 1,3,4-oxadiazole-based pyrazole derivatives as electronic-transporting molecules have been synthesized and characterized. Those compounds are convenient successful inducted a pyrazole chromophore and multiple 1,3,4-oxadiazole moieties by 1,3-dipolar-cyclization and dehydration-cyclization to promote the conjugation range and exhibit high thermal stability and good physical properties. The chromophore of pyrazole plays assistant role in controlling fundamental electroluminescent process. Spectroscopic studies, the measurements of cyclic voltammogram, thermal characterization and electroluminescent properties have revealed that 1,3,4-oxadiazole-based pyrazole derivatives are efficient blue-greenish electroluminescent materials.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 749 - 762
Published online: 10th March, 2006
DOI: 10.3987/COM-04-10299
An Unusual Lewis Acid Promoted Isomerization of trans-3-Halo-3-phenylthio-β-lactams

Shamsher S. Bari,* Paloth Venugopalan, Renu Arora, Garima Modi, and Sachin Madan

*Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh-160014, India


A method for C-3 epimerization of 3-halo-3-phenylthio-β-lactams, mediated by Lewis acids, is described. TiCl4 promotes isomerization of trans-3-chloro-3-phenylthioazetidin-2-ones (2) to cis-3-chloro-3-phenylthioazetidin-2-ones (3). TiBr4 promotes isomerization as well as substitution of chlorine with bromine affording isomeric cis- and trans-3-bromo-3-phenylthioazetidin-2-ones (5) and (6) respectively, while TiI4 is ineffective.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 763 - 769
Published online: 3rd March, 2006
DOI: 10.3987/COM-05-S(T)53
Synthesis of Novel Symmetric Cyclic Indole-tetramers

Hidetaka Hiyoshi,* Takaaki Sonoda, and Shuntaro Mataka

*Advanced Materials Department, Ihara Chemical Industry Co., Ltd., 2256, Nakanogo, Fujikawa-cho, Ihara-gun, Shizuoka 421-3306, Japan


The reaction of 5-bromoindolin-2-one with phosphoryl chloride in chlorobenzene gave a novel symmetric isomer of a cyclic indole-tetramer. This novel isomer was used in Suzuki-Miyaura coupling reaction to give tetraarylated derivatives of the cyclic indole-tetramer.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 771 - 777
Published online: 14th March, 2006
DOI: 10.3987/COM-05-10646
A Total Synthesis of (±)-Hop Ether

Ching-Han Lin, Yi-Lin Su, and Huo-Mu Tai*

*Department of Applied Chemistry, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan, R.O.C.


A total synthesis of the iridoid monoterpene (±)-hop ether (2) is described. The Norrish I type fragmentation of bicyclo[2.2.1]heptanone (5) is the key step.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 779 - 785
Published online: 3rd March, 2006
DOI: 10.3987/COM-05-10649
New Derivatives of 3-[(4-Phenyl-5-oxo-1,2,4-triazolin-1-yl)methyl]-4-substituted 1,2,4-Triazolin-5-one

Monika Wujec, Monika Pitucha, and Maria Dobosz*

*Department of Organic Chemistry, Faculty of Pharmacy, Medical University in Lublin, 6 Staszica Str., 20-081 Lublin, Poland


In the reaction of hydrazide of (4-phenyl-5-oxo-1,2,4-triazolin-1-yl)acetic acid (1) with isocyanate the respective semicarbazide derivatives (2) were obtained. Further cyclization with 2% NaOH led to the formation of [3-(4-phenyl-5-oxo-1,2,4-triazolin-1-yl)methyl]-4-substituted 1,2,4-triazolin-5-one (3) and (4-phenyl-5-oxo-1,2,4-triazolin-1-yl)acetic acid (4).

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 787 - 799
Published online: 7th March, 2006
DOI: 10.3987/COM-06-10665
Synthesis of 3-Cyanoflavones and Their Biological Evaluation

Frederic Lassagne, Isabelle Bombarda, Michel Dherbomez, Sourisak Sinbandhit, and Emile M. Gaydou*

*Phytochemistry Laboratory of Marseilles, Saint Jerome Faculty of Sciences and Technology, Paul Cezanne University, Escadrille Normandie Niemen avenue,13397 Marseille Cedex 20, France


The synthesis, using β-bromo-α-ethylthiocinnamonitrile (1) and methyl salicylate (2), of two new series of methyl 2-(2’-cyano-2’-ethylthio-1’-phenylvinyloxy)benzoates (3), precursors of 3-cyanoflavones (4) is reported. Compounds (3) and (4) were checked against representatives Gram-positive and -negative bacteria (Escherichia coli, Staphylococcus aureus and Enterococcus hirae). These compounds were quite inactive against bacteria, which is not the case for the two fungi strains investigated (Candida albicans and Saccharomyces cerevisiae). The presence of a 4’-substituent on the 3-cyanoflavone skeleton gives a different effect for S. cerevisiae. The presence of a methylendioxy substituent on the methyl 2-(2’-cyano-2’-ethylthio-1’-phenylvinyloxy)benzoates (3) enhance the effect in particular for C. albicans.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 801 - 806
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-10669
Synthesis of 1H-Pyrazolo[4’,3’:5,6]pyrimido[2,1-a]isoindol-4(10H)-ones. Derivatives of a New Ring System

Abolghasem Davoodnia, Mehdi Bakavoli,* Ali Vahedinia, Mohammad Rahimizadeh, and Mina Roshani

*Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad 91775-1435, Iran


Several derivatives of the new pyrazolo[4’,3’:5,6]pyrimido[2,1-a]isoindolone ring system (4) have been prepared through heterocyclization of 2-chloromethylbenzoyl chloride (1) with appropriately substituted 5-amino-1H-pyrozole-4-carbonitriles (2). The reaction intermediate inden-2-yl-1-phenyl-pyrazole-4-carbonitrile (3), on subjection to acid or base, underwent hydrolysis and cyclocondensation simultaneously to afford the tetracyclic compound (4).

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 807 - 810
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-10671
Synthesis of Some 1,3,5-Triazine Derivatives

Davood Azarifar* and Ali Forghaniha

*Department of Chemistry, School of Science, Bu-Ali Sina University, Hamadan 65174, Iran


Some derivatives of 1,3,5-triazine were prepared with excellent yields by nucleophilic reactions between cyanuric chloride and some nucleophiles under mild conditions.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 811 - 819
Published online: 10th March, 2006
DOI: 10.3987/COM-06-10672
Organopalladium Complexes 5-Amino-3H-1,3,4-thiadiazoline-2-thione as Metalloreceptor

Nam Sook Cho,* Mi Sun Park, Young Hoon Kim, Young-Ae Yu, Hyun Jung Kwon, and Yeong-Joon Kim

*Department of Chemistry, Chungnam National University, Yusung, Daejon 305-764, Korea


Macrocycles containing two 5-amino-3H-1,3,4-thiadiazoline-2-thione 5 linking the 2- and 5-positions of the heterocycle unit and one 1,3-benzenedime- thanethiol were prepared via the regiospecific S-alkylation of 5-amino-3H-1,3,4-thiadiazoline-2-thione. The 1,3-benzenedimethanethiol sites chelated to palladium metal ion to afford an organopalladium metalloreceptor. The structures of the macrocycles and metalloreceptors were established using 1H and 13C NMR, IR, MS spectrometry, and elemental analysis. The molecular recognition of the metalloreceptors (5a and 5b) was examined for some DNA/RNA nucleobases and some amino acid methyl ester by 1H NMR spectrometry. In case of 5a, the complexation ability increased in the order pyrazine / uracil /acetanilide < adenine < cytosine < phenylalanine methyl ester / tyrosine methyl ester. With 5b, the complexation ability also increased in the same order as 5a pyrazine / uracil 5a.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 821 - 828
Published online: 3rd March, 2006
DOI: 10.3987/COM-06-10678
Unexpected Reaction of 2-Hydrazinoperimidine with Maleic Anhydride: Syntheses of (8-Amino-9-oxo-9,10-dihydro-8H-imidazo[1,2-a]perimidin-10-yl)acetic Acid and Its Azomethine Derivatives

Anton V. Dolzhenko, Wai-Keung Chui,* and Anna V. Dolzhenko

*Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore


The reaction of 2-hydrazinoperimidine (3) and maleic anhydride in mild conditions afforded the formation of an unexpected product, namely (8-amino-9-oxo-9,10-dihydro-8H-imidazo[1,2-a]perimidin-10-yl)acetic acid (5). The possible mechanism of this reaction is discussed. Schiff bases (9a-f) were prepared from 5 using corresponding aldehydes. The structures of the prepared compounds were established with spectral analysis including NOESY 2D experiments.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 829 - 836
Published online: 14th March, 2006
DOI: 10.3987/COM-06-10687
Crystal Structure and Complexation Behavior of Quinonediimine Bearing Thiadiazole Unit

Mendra T. S. Ritonga, Harumi Shibatani, Hidehiro Sakurai, Toshiyuki Moriuchi, and Toshikazu Hirao*

*Department of Applied Chemistry, Graduate School of Science, Osaka University, 2-1 Yamadaoka, Suita, Osaka 560-0871, Japan


The single crystal X-Ray structure determination of aniline oligomers composed of a benzothiadiazole unit revealed the twisted conformation in the crystal state. Despite π-conjugation, the quinonediimine (2) exhibited the more twisted conformation compared with the p-phenylenediamine (1). The benzothiadiazole ring was also found to control the arrangement through π-π interaction in the crystal packing. The controlled complexation of 2 with Pd(MeCN)4(BF4)2 was achieved by the N-heterocyclic coordination sites.

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Note | Regular issue | Vol 68, No. 4, 2006, pp. 837 - 840
Published online: 10th March, 2006
DOI: 10.3987/COM-06-10694
Methylation of Non-acidic Alcohols of Alkaloids with TMS-diazomethane: Conversion of Codeine to Codeine-6-methyl Ether

Christopher W. Cunningham, Linn N. Thatcher, and Andrew Coop*

*Department of Pharmceutcial Sciences, School of Pharmacy, University of Maryland, 20 Penn Street, Baltimore, MD 21201, U.S.A.


Trimethylsilyldiazomethane (TMS-CHN2) is a convenient agent for the methylation of acidic alcohols, and is known to methylate non-acidic alcohols in CH2Cl2 by the addition of HBF4. Herein, we show that silica gel acts as a suitable alternative for alkaloids, without causing precipitation of the salt from the reaction mixture.

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19 data found. 1 - 19 listed