HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 68, No. 10, 2006
Published online: 1st August, 2006
■ Synthesis and Properties of Oligocarboxamide Molecular Strands Containing 1,8-Naphthyridine and Pyridine Groups
Hisakazu Miyamoto,* Takahiro Ikeuchi, Atsushi Fujioka, Jean-Marie Lehn,* Shigeru Ohba,* and Yohji Misaki
*Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama, Ehime 790-8577, Japan
Abstract
Oligocarboxamide molecular strands based on carboxamide between 1,8-naphthyridine and pyridine, pyridine and pyridine, 1,8-naphthyridine and benzene, and pyridine and benzene have been prepared. They have afforded various inclusion complexes with organic solvents. Structural features of the inclusion complexes determined by X-Ray crystal structure analyses are described.
Published online: 1st August, 2006
■ Synthesis of Vigabatrin®
Meng-Yang Chang,* Chun-Yu Lin, and Chi-Wi Ong
*Department of Applied Chemistry, National University of Kaohsiung, Kaohsiung 811, Taiwan, R.O.C.
Abstract
A concise synthesis of vigabatrin® has been achieved from trans-(2S,4R)-4-hydroxyproline via the key regioselective Baeyer-Villiger lactonization reaction.
Published online: 28th July, 2006
■ Synthesis of Novel Pyrimido[4,5-c]pyridazines and 1,2-Dihydro-3a,7,9,9b-Tetraaza-cyclopenta[a]naphthalen-3-ones as Potent Inhibitors of Lymphocyte Specific Kinase (LCK)
John C. VanRens, Mark Sabat,* Todd A. Brugel, Jennifer Maier, Matthew J. Laufersweiler, Adam Golebiowski, Steve Berberich, and Biswanath De
*P&G Pharmaceuticals, Health Care Research Center, 8700 Mason-Montgomery Rd, Mason, OH 45040, USA
Abstract
This paper details the synthesis of a novel class of 1,2-dihydro-pyrimido[4,5-c]pyridazines and substituted 1,2-dihydro-3a,7,9,9b- tetraaza-cyclopenta[a]naphthalen-3-one. The most potent analogs disclosed showed low nanomolar activity for the inhibition of lck kinase.
Published online: 25th August, 2006
■ A Convenient Synthesis of Functionalized 1H-Pyrimidine-2-ones/thiones, Pyridazine and Imidazole; Experimental Data and PM3 Calculations
Emin Saripinar,* Çigdem Yilmaz, Dilek Ünal, Ilhan Özer Ilhan, Nihal Yazir, and Yunus Akçamur
*Department of Chemistry, Arts and Sciences Faculty, Erciyes University, 38039, Kayseri- Turkey
Abstract
The 4-(4-methoxybenzoyl)-5-(4-methoxyphenyl)-2,3-dihydro-2,3-furandione (1) and semicarbazones and thiosemicarbazones (2a-h) combine with loss of carbon dioxide and water yielding the 1-methylenaminopyrimidin-2-one and thione derivatives (3a-h) in moderate yields (33-55%). Hyrolysis of 3a and 3e leads to the 1-aminopyrimidin-2-one/thione (4a, b), pyrimidine (6, 11), pyridazine (8, 13) and imidazole (10) derivatives were obtained from the reactions of 1 and Ethyl-4,5-dioxo-2-phenyl-4,5-dihydrofuran-3-carboxylate (12) with 1,5-diphenylcarbazide (5), 4-phenylsemicarbazide (7) and 1-phenylsemicarbazide (9). The electronic and geometric structures of reactants, transition states, intermediates and final products of the reaction of model reactants; 2,3-dihydro-1H-furan-2,3-dione and semicarbazone are calculated by the PM3 method. Transition states are further confirmed by vibrational analysis (computation of force constants analytically) and characterised by the corresponding imaginary vibration modes and frequencies.
Published online: 25th August, 2006
■ Synthesis of Novel Pyrazolopyrrolizinones as Prospective Anticancer Agents
Christophe Rochais, Jana Sopkovà-de Oliveira Santos, Patrick Dallemagne, and Sylvain Rault*
*CERMN, Faculty of Pharmacy, 1, rue Vaubénard, 14032 Caen Cedex, France
Abstract
Herein we describe the access of novel pyrazolopyrrolizinones from commercial arylacetonitriles. The first step conducts to the corresponding aminoester which was first submitted to Clauson-Kaas procedure. Amidification and cyclisation afford then the first examples of the expected heterocycles. In order to improve the sequence and to obtain N-substituted isomers, 3-aryl-5-(pyrrolidin-1-ylcarbonyl)-4-(1H-pyrrol-1-yl)-1H-pyrazoles (5) were alkylated and conduct to two different N-substituted pyrazoles. These novel products were separated by chromatography and clearly identified using different analytical techniques. Application of the cyclisation procedure conducts then to the two corresponding final title products.
Published online: 1st August, 2006
■ Synthesis of Enantiopure 3,5-Disubstituted Pyrrolidines by Ring-Opening/Cross-Metathesis Reaction of 2-Azanorbornene Derivatives
Odón Arjona,* Ma José Cabas, José Nieto-Rubio, and Ana Querejeta
*Department of Organic Chemistry, Faculty of Chemistry, Complutense University, E-28040, Madrid, Spain
Abstract
A concise method for the synthesis of enantiopure 3,5-disubstituted pyrrolidines from 2-azanorbornene derivatives is described. The method is also applied to the synthesis of 3,5-disubstituted prolines.
Published online: 29th August, 2006
■ An Efficient Synthesis of 1,4-Dihydro-6-trifluoromethylpyridines: A Facile and Useful Method for Dehydration of α-Trifluoromethyl Alcohols by Use of Phosphorous Oxychloride/Pyridine Adsorbed on Silica Gel
Isamu Katsuyama,* Kazumasa Funabiki, Masaki Matsui, Hiroshige Muramatsu, and Katsuyoshi Shibata
*Hitec Co., Ltd, OAP 25F, 1-8-30 Temmabashi, Kita-ku, Osaka-shi, Osaka 530-6025, Japan
Abstract
The treatment of α-alkoxycarbonyl-α,β-unsaturated trifluoromethyl ketones (1) with β-aminocrotonates (2) affords 2-hydroxy-6-methyl-2- trifluoromethyl-1,2,3,4-tetrahydropyridines (3), which undergo facile dehydration by use of phosphorus oxychloride / pyridine adsorbed on silica gel, giving good to high yields of 1,4-dihydro-2-methyl-6-trifluoromethylpyridines (4).
Published online: 22nd August, 2006
■ Mucoralactone A: An Unusual Steroid from the Liquid Culture of Mucor plumbeus
Athar Ata,* Leigha J. Conci, and Ilkay Orhan
*Department of Chemistry, The University of Winnipeg, 515 Portage Avenue, Winnipeg, Manitoba, R3B 2E9, Canada
Abstract
Mucoralactone A (1), a novel steroid, was isolated from the liquid culture of Mucor plumbeus. Its structure was elucidated with the aid of extensive spectroscopic studies. Mucoralactone A (1) has a lactone moiety incorporated in its structure, and exhibited acetylcholinesterase enzyme inhibition activity with an IC50 value of 19 μM and modest antifungal activity against Candida albicans.
Published online: 1st August, 2006
■ Synthesis of 1,3-Selenazetidine Derivatives from Imines and Thiocarbamoyl Isoselenocyanate
Mamoru Koketsu,* Toshihiro Otsuka, and Hideharu Ishihara*
*Division of Instrumental Analysis, Life Science Research Center, Gifu University, Gifu 501-1193, Japan
Abstract
Reactions of thiocarbamoyl isoselenocyanate with imines afforded 1,3-selenazetidines under reflux conditions. We could confirm the structure using significant difference of chemical shifts between selenazetidines and selenoureas including cyclic selenoureas in 77Se NMR spectra.
Published online: 11th August, 2006
■ Phenylcarbamoylation of N-Acetyl-1,2,4-triazolium-4-aminides Revisited
Dietrich Moderhack* and Matthias Noreiks
*Institute of Pharmaceutical Chemistry, Technical University, D-38106 Braunschweig, Germany
Abstract
The reaction of N-acetyl-1,2,4-triazolium-4-aminides (I, i.e. 1Aa-d) with phenyl isocyanate affords ring functionalized products (4a-d) rather than linear adducts (II). Analogous compounds are obtained from the triazolium-1-aminide (1Ae) and the imidazolium congener (1Af). Twofold carbamoylation to give products of type (8) occurs on reaction of aminotriazolium salts (7A) in the presence of base. Azoliums having methyl at C(5) / (2) are inert throughout (B series).
Published online: 28th July, 2006
■ Synthesis of Novel Naphthoquinone Fused Cyclic α-Aminophosphonates
Bin Wang, Zhiwei Miao, You Huang, and Ruyu Chen*
*State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People’s Republic of China
Abstract
The synthesis of a novel quinone fused phosphorus heterocycle, 2-phenoxy-3,4-dihydro-2H-naphtho[2,3-e][1,4,2]oxazaphosphinane-5,10-dione- 2-oxides (3a-g), is described for the first time. The products can be obtained easily by one-pot of three-component condensation reaction.
Published online: 1st September, 2006
■ A Highly Efficient Synthesis of (–)-Pinidinol
Julian Gebauer, Daniel Rost, and Siegfried Blechert*
*Technical University of Berlin, Institute of Chemistry, Strasse des 17. Juni 135, D-10623 Berlin, Germany
Abstract
A short step synthesis of the bioactive piperidine alkaloid (–)-pinidinol was achieved using a cross metathesis and a reductive amination as the key steps.
Published online: 1st August, 2006
■ Practical Synthesis of New Chiral Cis-Phthalazinones with Potential for High Phosphodiesterase(PDE4) Inhibitory Activity
Tinh Van Dang, Chung Keun Jin, Motoyuki Miyamoto, Yoshifumi Ikee, Takashi Masuda, Shigeki Sano, Motoo Shiro, and Yoshimitsu Nagao*
*Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan
Abstract
New chiral cis-tetrahydrophthalazinones were synthesized directly from the corresponding chiral (4R)- and (4S)-isopropyl-1,3-thiazolidine-2-thione amides in one-pot reaction involving mild aminolysis with hydrazine monohydrate followed by intramolecular condensation.
Published online: 1st August, 2006
■ Preparation of 2-Amino-1,3-selenazoles by Reaction of N,N-Unsubstituted Selenoureas with α,β-Unsaturated Ketones in Alcohol
Mamoru Koketsu,* Koichi Kanoh, and Hideharu Ishihara*
*Division of Instrumental Analysis, Life Science Research Center, Gifu University, Gifu 501-1193, Japan
Abstract
2-Dialkylamino-1,3-selenazoles were yielded by the reaction of N,N-unsubstituted selenoureas with α,β-unsaturated ketones in alcohol in the presence of ferric chloride at room temperature.
Published online: 22nd August, 2006
■ Synthesis of Diaryl Ether-Linked Porphyrin Dimers via Ullmann Coupling Reaction
Xu-Liang Jiang, Hong-Liang Zhang, and Jian Wu*
*Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
Abstract
Diaryl ether-linked porphyrin dimers were synthesized by CuI-catalyzed Ullmann coupling reaction between 5-(4-hydroxylphenyl)-10,15,20-triphenylporphyrin and 5-(4-iodophenyl)-10,15,20- triphenylporphyrin as well as their metalated derivatives.
Published online: 28th July, 2006
■ A Butenolide from the Marine Sponge Callyspongia vaginalis
Tanya H. Layne and Winston F. Tinto
*Laboratory of Bioorganic Chemistry, Department of Biological and Chemical Sciences, University of the West Indies, Cave Hill Campus, Bridgetown, Barbados, BB10000, West Indies
Abstract
A butenolide identified as 5-hydroxy-3-methyl-5- pentyl-2, 5-dihydrofuran-2-one (1) was isolated from Callyspongia vaginalis. Structural elucidation was achieved via spectroscopic means including 1D and 2D NMR experiments.
Published online: 22nd August, 2006
■ Stereoselective Synthesis and Isomerization of the Indole Alkaloid Murrayacarine
Ann-Louise Johnson, Johnny Slätt, Tomasz Janosik, and Jan Bergman*
*Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park, SE-141 57 Huddinge, Sweden
Abstract
A short and efficient stereoselective synthesis of the indole alkaloid murrayacarine is described, including studies on its acid-induced isomerization.
Published online: 29th August, 2006
■ Efficient Synthesis and Crystal Structure of New 1,4-Ansa-anthraquinone
Chitoshi Kitamura,* Jun Fujimoto, Nobuhiro Kawatsuki, and Akio Yoneda
*Department of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2201, Japan
Abstract
An ansa-anthraquinone with decamethylene-dioxa spacer was prepared by two-step or direct cyclization. The solid state structure was characterized by single crystal X-Ray diffraction analysis.
Published online: 22nd August, 2006
■ 1,3-Dipolar Cycloadditions in Aqueous Media
Giorgio Molteni
*University of Milan, Department of Organic and Industrial Chemistry, via Golgi 19, 20133 Milan, Italy
Abstract
1,3-Dipolar cycloadditions in aqueous media represents a useful, non conventional protocol in the synthesis of a variety of five-membered heterocycles. In addition, water as the solvent may significantly enhance cycloaddition rates and/or stereoslectivities. The literature data on this subject are reviewed in a systematic way, with an emphasis to improvements with respect to cycloadditions performed in the usual, non-aqueous conditions.