Regular Issue

Vol. 83, No. 2, 2011

14 data found. 1 - 14 listed
Contents | Regular issue | Vol 83, No. 2, 2011
Published online:
DOI: 10.3987/Contnets-11-83-02
Review | Regular issue | Vol 83, No. 2, 2011, pp. 247 - 273
Published online: 19th November, 2010
DOI: 10.3987/REV-10-681
Development of Trialkyl(2-indolyl)borates as Potential Synthetic Intermediates

Minoru Ishikura*

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


This account deals with our investigation of the reaction and synthetic use of indolylborates as versatile synthetic tools; 1) palladium-catalyzed cross-coupling reaction and its use for the synthesis of indole alkaloids and 2) intramolecular alkylmigration in indolylbotrates for the construction of highly elaborate indole derivatives.

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Review | Regular issue | Vol 83, No. 2, 2011, pp. 275 - 291
Published online: 27th December, 2010
DOI: 10.3987/REV-10-685
Synthesis, Properties and Structures of Phosphorus-Nitrogen Heterocycles

Vasile Simulescu,* Eleonora Crasmareanu, and Gheorghe Ilia

*Department of Organic Chemistry, Institute of Chemistry, Timisoara of the Romanian Academy, 24 Mihai Viteazu Bvd., 300223-Timisoara, Romania


The synthesis, properties and structures of heterocyclic molecules containing phosphorous and nitrogen are described in this review. A systematic synthesis of a ring compound needs one or more bifunctional starting molecules that react in a special way to form new bonds and to obtain the ring. Oligomers or polymers can be obtained besides other products resulting from leaving groups necessary to form the new bonds. Hydrazine for example is one of the simplest bifunctional compounds that must be able to introduce two vicinal nitrogen atoms into a cycle, as it will be shown further.

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Communication | Regular issue | Vol 83, No. 2, 2011, pp. 293 - 298
Published online: 28th December, 2010
DOI: 10.3987/COM-10-12106
Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions

Hisashi Takada, Shinji Nagumo,* Eiko Yasui, Megumi Mizukami, and Masaaki Miyashita*

*Department of Applied Chemistry, Faculty of Engineering, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo, 192-0015, Japan


The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the α,β-unsaturated γ,δ-epoxy ester system and an epoxy alcohol derivative as the key steps.

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Paper | Regular issue | Vol 83, No. 2, 2011, pp. 299 - 309
Published online: 27th December, 2010
DOI: 10.3987/COM-10-12081
The Synthesis of Novel Palladium(II) Carbene Complexes, Azolium Salts and Their Catalytic Properties

Beyhan Yiğit, Murat Yiğit,* İsmail Özdemir, and Engin Çetinkaya

*Department of Chemistry, Faculty of Arts and Sciences, Adıyaman University, 20240 Adıyaman , Turkey


Novel three 1,3-bis[2-(N,N’-diisopropylamino)ethyl]imidazolinium, 1,3-bis[2-(N,N’-diisopropylamino)ethyl]benzimidazolium and 1-(2-diisopropyl- aminoethyl)-3-(2-methoxyethyl)benzimidazolium chloride salts (1, 3a-b) and two palladium complex (2, 4) have been prepared and characterized by C, H, N analysis, 1H NMR and 13C NMR and they have been investigated their catalytic activity in the Heck and Suzuki coupling reactions.

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Paper | Regular issue | Vol 83, No. 2, 2011, pp. 311 - 322
Published online: 14th January, 2011
DOI: 10.3987/COM-10-12099
Investigations into the Nucleophilic meso-Substitution of F-BODIPYs and Improvements to the Synthesis of 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene

Sarah M. Crawford and Alison Thompson*

*Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3, Canada


A series of three F-BODIPYs, with varying levels of steric crowding about the meso-position were selected to investigate nucleophilic meso-substitution of F-BODIPYs. The synthesis of one of these F-BODIPYs, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (totally unsubstituted dipyrrin skeleton), was optimized to give higher yields over routine literature procedures. This modified procedure involves oxidation of a dipyrromethane using p-chloranil, instead of DDQ, to give a dipyrrin which is then trapped in situ as its BF2 complex. Nucleophilic meso-alkylation of the series of F-BOIDPYs with n-butyllithium gave meso-butyl F-BODIPYs in moderate to good yields. This work represents a new, synthetically viable method for the synthesis of meso-alkylated F-BODIPYs. Extension of the nucleophilic substitution methodology to meso-arylation was possible. However, the reaction was unselective: substitution at boron, to give the boron-diaryl C-BOIDPYs, occurred preferentially to nucleophilic meso-substitution and thus a mixture of products was obtained.

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Paper | Regular issue | Vol 83, No. 2, 2011, pp. 323 - 330
Published online: 17th December, 2010
DOI: 10.3987/COM-10-12102
Efficient Synthesis of Functionalized Diazacyclopenta[c]pentalene with Multiple Intermolecular Interactions in Crystal

Konstantin V. Kudryavtsev*

*Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, 119991, Moscow, Russia


Atom economic synthesis of functionalized polysubstituted racemic diazacyclopenta[c]pentalene 7 has been developed using sequential organocatalytic 1,3-dipolar cycloaddition of azomethine ylide with maleic anhydride and three successive amide bonds formation induced by interaction of 4-fluorobenzylamine with heterocyclic anhydride 5. Enantiomers of 7 are connected by Cl-π, H···F and C=O···H intermolecular interactions in crystal.

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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp. 331 - 338
Published online: 27th December, 2010
DOI: 10.3987/COM-10-12078
Dowex-50W Promoted Friedländer Synthesis of Substituted Quinolines under Solvent-Free Conditions

Huey-Min Wang,* Rei-Sheu Hou, Hau-Dung Du, Iou-Jiun Kang, and Ling-Ching Chen*

*Department of Cosmetic Science, Chung Hwa University of Medical Technology, Department of Chemistry, National Cheng Kung University, Tainan, 701, Taiwan, R.O.C.


An efficient method for the synthesis of substituted quinolines using Dowex-50W ion exchange resin as reusable eco-friendly catalyst vai Friedländer annulation under solvent-free conditions is described.

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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp. 339 - 349
Published online: 1st December, 2010
DOI: 10.3987/COM-10-12093
Synthesis and Reactions of a New Series of 1,2,4-Triazolo[4,3-c]quinazolines

Kamal F. M. Atta,* Mohamed G. Marei, and Fatma A. M. Mohamed

*Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt


3-Ethoxycabonyl-1,2,4-triazolo[4,3-c]quinazoline (2) has been synthesized in excellent yield by the condensation of 4-hydrazinoquinazoline (1) with diethyl oxalate and was converted into 3-carbohydrazide 3. The later product was treated with potassium thiocyanate, phenylisothiocyanate or carbon disulfide followed by reaction with hydrazine hydrate to give the respective new 1,2,4-triazolo[4,3-c]quinazoline derivatives 4, 8 or 12. Dehydrative cyclization of the later compounds with concentrated sulphuric acid, sodium hydroxide, m-bromobenzoic acid, carbon disulfide, oxalic acid, phenacyl bromide or benzoin yielded the target heterocycles namely, 1,3,4-thiadiazole, 1,2,4-triazole, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole or 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine incorporating 1,2,4-triazolo[4,3-c]quinazoline ring. The structure of the above compounds was confirmed from their spectral characteristics.

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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp. 351 - 356
Published online: 10th December, 2010
DOI: 10.3987/COM-10-12094
New Type Indole Diterpene, Eujindoles, from Eupenicillium javanicum

Shou Nakadate, Koohei Nozawa,* Hitoshi Horie, Yuichi Fujii, and Takashi Yaguchi

*School of Pharmaceutical Sciences, Ohu University, 31-1 Misumido, Tomita-machi, Koriyama, Fukushima 963-8611, Japan


Two new indole diterpenes, 17-hydroxyeujindole (1) and 17-oxoeujindole (2), were isolated from the extract of Eupenicillium javanicum IFM 59075 (UC62). The structures containing the absolute configuration were determined by spectroscopic methods.

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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp. 357 - 363
Published online: 13th January, 2011
DOI: 10.3987/COM-10-12096
Regio-Controlled Synthesis of 1,4-Benzothiazinones

Touria Ghailane, Mohammed Saadouni, Said Boukhris, Nouzha Habbadi, Amina Hassikou, Abdelali Kerbal, Bernard Garrigues, and Abdelaziz Souizi*

*Laboratoire de Synthèse Organique, Organométallique et Théorique, Faculté des Sciences, Université Ibn Tofail, B. P 133-Kénitra, Morocco


Regio-controlled cyclization of gem-dicyanoepoxides with 2-aminothiophenol and its hydrochloride to form 1,4-benzothiazine-2-one or 3-one is described. The cyclization is highly regioselective and the reaction of the epoxides with 2-aminothiophenol under neutral reaction condition gave 1,4-benzothiazine-2-one as a sole cyclized product, whereas that with hydrochloride of 2-aminothiophenol afforded 1,4-benzothiazine-3-one predominantly. The regioselectivity resulted from the reaction condition is discussed.

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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp. 365 - 370
Published online: 27th December, 2010
DOI: 10.3987/COM-10-12098
A Facile Synthesis of 2-Substituted 2,3-Dihydro-4(1H)-azuleno[1,2-d]pyrimidinones

Dao-Lin Wang,* Yuan-Feng LI, Jiao Xu, Wei Li, Shao-Fei Li, and Li-Nan Lin

*Liaoning Key Laboratory of Synthesis and Application of Functional Compound, College of Chemistry & Chemical Engineering, Bohai University, Jinzhou 121001, China


A facile, efficient and novel approach to access 2-substituted 2,3-dihydro-4(1H)-azuleno[2,1-d]pyrimidinones was developed by condensation of methyl 2-amino-3-carbamoylazulene-1-carboxylate with ketones or ary1 aldehydes in the 2,2,2-trifluoroethanol catalyzed by p-toluenesulfonic acid.

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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp. 371 - 383
Published online: 27th December, 2010
DOI: 10.3987/COM-10-12101
The Synthesis of Some Derivatives Based on the 4-Benzyl-1H-pyrazole-3,5-diamine Core

Lukáš Jedinák, Vladimír Kryštof, and Petr Cankař*

*Department of Organic Chemistry, Palacký University, Trida Svobody 8, 77146 Olomouc, Czech Republic


The three-step synthesis of 4-benzyl-1H-pyrazole-3,5-diamines 2 from commercially available aldehydes 3 is given. The Knoevenagel condensation was utilized to assemble the initial carbon framework, resulting in the benzylidenemalononitriles 4 which were directly transformed by the reduction of the electron deficient C=C bond to benzylmalononitriles 5. Subsequent cycloaddition of hydrazine with 5 afforded the desired pyrazoles 2. Due to the high similarity with 4-arylazo-1H-pyrazole-3,5-diamines, the biological activities of the 4-benzyl-1H-pyrazole-3,5-diamines 2 were evaluated while focusing on the inhibition of cyclin-dependent kinases (CDKs), but no significant results were obtained.

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Short Paper | Regular issue | Vol 83, No. 2, 2011, pp. 385 - 393
Published online: 27th December, 2010
DOI: 10.3987/COM-10-12105
Synthesis and Biological Activities of Some N-Acyl-2,6-diaminopyridines and Related Linker Mode Identical Twin Drugs

Nobuko Mibu, Kazumi Yokomizo, Miyuki Saisho, Marumi Oishi, Hatsumi Aki, Takeshi Miyata, and Kunihiro Sumoto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


In connection with our studies on biologically active compounds in the class of N-acyl-2,6-diaminopyridines, some molecular modifications were attempted. All of the synthesized compounds were evaluated for biological activity with herpes virus type 1 (HSV-1) by a plaque reduction assay. We observed that most of the synthesized derivatives showed no significant anti- HSV-1 activity, but we found that compounds 5 and 6 with a branched long alkyl chain showed high cytotoxicity to Vero cells.

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14 data found. 1 - 14 listed