HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Special Issue
Akira Suzuki's Special Issues,Vol. 80, No. 1, 2010
Published online: 18th August, 2009
■ A Simple Approach to the Synthesis of Furofurans and Furopyrroles Using 3-Phenacylated Tetrahydro-2-imino-3-furancarbonitriles
Hiroshi Maruoka,* Fumi Okabe, Eiichi Masumoto, Toshihiro Fujioka, and Kenji Yamagata
*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
Abstract
A new and easy synthetic route to furo[2,3-b]furans 7a−d and furo[2,3-b]pyrroles 8a−d has been achieved by the C-phenacylation/cyclization reactions of 2-amino-4,5-dihydro-3-furancarbonitrile (5). Thermal treatment of the key intermediate 3-phenacylated tetrahydro-2-imino-3-furancarbonitriles 6a−d, which were prepared from compound 5 and phenacyl bromides, e.g. phenacyl bromide, 4-chlorophenacyl bromide, 4-methylphenacyl bromide and 4-methoxyphenacyl bromide, with acetic anhydride caused intramolecular cyclization to yield the corresponding furo[2,3-b]furans 7a−d. On the other hand, methanolic sodium methoxide-assisted cyclocondensation of compounds 6a−d gave the corresponding furo[2,3-b]pyrroles 8a−d.
Published online: 19th August, 2009
■ Novel Formation of Dipyrrolo- and Diindolo[1,2-a:2’,1’-c]quinoxaline Derivatives and Their Optical Properties
Shoji Matsumoto,* Sheng Qu, Takamitsu Kobayashi, Masahiro Kanehiro, Motohiro Akazome, and Katsuyuki Ogura
*Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Abstract
Dipyrrolo- and diindolo[1,2-a:2’,1’-c]quinoxaline structures (A and B, respectively) were synthesized from 1,2-di(1-pyrrolyl)- and 1,2-di(1-indolyl)benzene derivatives with iodine using a novel intramolecular coupling reaction. Apparent differences between A and B were observed from UV-VIS absorption and fluorescence spectra. Sharp peaks with a fine structure were observed in the absorption and fluorescence spectra of diindolo[1,2-a:2’,1’-c]quinoxaline (2b). Introduction of a phenyl ring at the 6 and 6’ positions of the indole moieties of 2b is efficient for imparting a red shift. In addition, the electron-withdrawing group at those positions particularly affected the emission peaks.
Published online: 1st September, 2009
■ Water in Amine-Mediated Single Electron Transfer Reaction of N-Allylic Trichloroacetamides
Tsuyoshi Taniguchi, Masamichi Sasaki, and Hiroyuki Ishibashi*
*Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan
Abstract
Water contaminating 1,4-dimethylpiperazine was thought to play an important role in effecting a single electron transfer reaction (radical cyclization) of N-allylic trichloroacetamides.
Published online: 20th August, 2009
■ Synthesis of Fluorinated 2,3-Disubstituted Benzofurans Potential β-Amyloid Aggregation Inhibitors
Marek Zaidlewicz,* Tomasz Kosmalski, Tathagata Sengupta, Kochupurackal P. Mohanakumar, and Krzysztof Staszak
*Department of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Abstract
A convenient synthesis of 2-[4’-(3-diethylaminopropoxy)phenyl]-3-(2-fluoro¬benzoyl)benzofuran, 3-(4-fluorobenzoyl)- and 3-(4-trifluoromethylbenzoyl) derivatives, via the Suzuki cross-coupling reaction as the key transformation, is described.
Published online: 25th August, 2009
■ A Concise Synthesis of 6,7-Dihydro-5H-dibenz[c,e]azepin-5-one
Young-Hyoung Goh, Guncheol Kim, Bum Tae Kim, and Jung-Nyoung Heo*
*Medicinal Chemistry Research Center, Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea
Abstract
A concise and efficient strategy for the synthesis of dibenz[c,e]azepin-5-ones has been developed. The approach relies on a key transformation involving Suzuki-Miyaura coupling of 2-bromobenzyl azides with 2-(methoxycarbonyl)phenylboronic acid, followed by either a stepwise sequence involving Staudinger reaction and lactam formation or one-pot hydrogenation/base-mediated intramolecular lactam formation.
Published online: 25th August, 2009
■ Synthesis of 3-Substituted 3-(Trimethylsiloxy)pyrrolidines from β-Aminoketones and Lithium Trimethylsilyldiazomethane
Yoshiyuki Hari, Takuya Yokoyama, and Toyohiko Aoyama*
*Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan
Abstract
Lithium trimethylsilyldiazomethane reacted with N-benzyl-β-aminoketones at -78 °C in THF to give 3-substituted 1-benzyl-3-(trimethylsiloxy)pyrrolidines in moderate to good yields.
Published online: 27th August, 2009
■ Synthesis of Oxidized Fatty Acid Derivatives via an Iodolactonization Reaction
Toshimasa Itoh, Nobuko Yoshimoto, and Keiko Yamamoto*
*Laboratory of Drug Design and Medicinal Chemistry, Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
Abstract
To study structure-activity relationships of oxidized fatty acids for the activation of peroxisome proliferator-activated receptors (PPARs), which are ligand-dependent transcription factors, we synthesized a series of oxidized fatty acids via iodolactone as a key intermediate.