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
30th Anniversary's Special Issues, Vol. 61, No. 1, 2003
Published online: 4th August, 2003
■ Synthesis of a Cage-annulated Ditopic Receptor
Alan P. Marchand,* Vinayak K. Gore, and Gadthula Srinivas
*Department of Chemistry, University of North Texas, Denton, TX 76203, U.S.A.
Abstract
The synthesis of a cage-annulated ditopic receptor (2) is described along with that of a corresponding model compound (3). Compound (2) is designed for use as a host system for selective complexation and transport of NaOH from aqueous alkaline media into organic media.
Published online: 4th August, 2003
■ Synthesis of 2-Pyrrolidinol Metabolite of OPC-51803, a Vasopressin V2 Receptor Agonist
Yoshikazu Kawano, Jun Matsubara,* Kazuyoshi Kitano, Tadaaki Ohtani, Kenji Otsubo, Makoto Komatsu, Minoru Uchida, and Fujio Tabusa
*Medicinal Chemistry Research Institute, Otsuka Pharmaceutical Co., Ltd., Kagasuno 463-10, Kawauchi-cho, Tokushima, Tokushima 771-0192, Japan
Abstract
The unstable 2-pyrrolidinol derivative (2), as a metabolite of a new vasopressin V2 receptor agonist OPC-51803 (1), was synthesized by the cytochrome P-450 model reaction of 1 with the Fe-salen complex and iodosobenzene.
Published online: 6th October, 2003
■ A New Aurone Glucoside and a New Chalcone Glucoside from Bidens bipinnata Linne
Shuai Li, Hai-Xue Kuang, Yoshihito Okada, and Toru Okuyama*
*Meiji Pharmaceutical Uni1versity, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan
Abstract
A new aurone glucoside, bidenoside A, (Z)-6-O-(3, 6-di-O-acetyl-É¿-D-glucopyranosyl)-6, 7, 3’, 4’-tetrahydroxyaurone (1) and a new chalcone glucoside, bidenoside B, 2’, 4’, 6’-trimethoxy-4-O-É¿-D-glucopyranosyl -dihydrochalcone (4), together with five known constituents have been isolated from the aerial parts of Bidens bipinnata. These structures have been elucidated on the basis of spectroscopic methods.
Published online: 2nd October, 2003
■ A Stereocontrolled Synthesis of (R)- and (S)-Azatyrosines
Giuseppe Cremonesi, Piero Dalla Croce,* Concetta La Rosa, and Enrica Pizzatti
*Dipartimento di Chimica Organica e Industriale, C.N.R. - I.S.T.M., Via Venezian 21, I-20133 Milano, Italy
Abstract
An asymmetric synthesis of (R)- or (S)- azatyrosine, starting from (2S)- or (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (5) (Schöllkopf reagent) and 5-benzenesulfonyloxy-2-hydroxymethylpyridine (3), is reported. The diastereocontrolled addition gives mainly one of two possible adducts with the (2S, 5R) or (2R, 5S) configuration respectively. After the removal of the chiral auxiliary and benzenesulfonyloxy group, azatyrosine is obtained in good yields and high ee.
Published online: 11th August, 2003
■ Selenium-containing Heterocycles from Isoselenocyanates: Synthesis of 2-Arylaminoselenazolo[5,4-b]pyridines
Plamen K. Atanassov, Anthony Linden, and Heinz Heimgartner*
*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
Abstract
The reaction of 3-amino-2-chloropyridine (4) with aryl isoselenocyanates (2a-d) in refluxing 2-propanol gave the hydrochlorides of 2-arylaminoselenazolo[5,4-b]pyridines (7a-d) in good yield. The free bases (8a-d) were obtained after treatment with aqueous NaOH and recrystallization. A reaction mechanism via the intermediate selenourea derivatives (5) is most likely. The structure of the 2-phenylamino derivative (8a) has been established by X-Ray crystallography.
Published online: 22nd September, 2003
■ Design and Synthesis of Novel Spiro Pyridinium and Quinolinium Salts
Mahesh L. Patil, Shinobu Takizawa, and Hiroaki Sasai*
*The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan
Abstract
Syntheses of novel spiro bis-pyridinium and bis-quinolinium salts have been achieved in three steps via intramolecular N-alkylation.
Published online: 2nd October, 2003
■ Juncin N, a New Briarane-Type Diterpenoid from the Gorgonian Coral Junceella juncea
Ping-Jyun Sung,* Tung-Yung Fan, Lee-Shing Fang, Jyh-Horng Sheu, Shwu-Li Wu, Guey-Horng Wang, and Mei-Ru Lin
*National Museum of Marine Biology and Aquarium, 2 Houwan Road, Checheng, Pingtung 944, Taiwan, Taiwan, R.O.C.
Abstract
A new chlorinated briarane-type diterpenoid, juncin N (1), has been isolated from the gorgonian coral Junceella juncea. The structure, including the relative configuration of the new compound (1), was elucidated by the combination of extensive spectral data analysis, especially in 1D and 2D NMR.
Published online: 14th October, 2003
■ Modification of Macrocyclic Compounds by Azaheterocycles
Nadezhda A. Itsikson, Gennady L. Rusinov, Dmitry G. Beresnev, and Oleg N. Chupakhin
*Institute of Organic Synthesis of Russian Academy of Sciences, 620219 Ekaterinburg, Russia
Abstract
Synthesis, modification and properties of macrocycles, such as crown ethers, their open-chain analogues, i.e. podands, calixarenes and resorcinarenes, having azaheterocyclic fragment are discussed.
Published online: 14th November, 2003
■ [π4+π2]Cycloadditions of Isothiazole Derivatives
Bärbel Schulze,* Dina Gidon, Anja Siegemund, and Ludmila L. Rodina
*Leipzig University, Institute of Organic Chemistry, D-04103 Leipzig, Johannisallee 29, Germany
Abstract
Dienophilic transformations of isothiazol-3(2H)-one 1,1-dioxides (I), 1-oxides (IV), α,ß-unsaturated γ-sultams (III), and cyclic vinyl p-tolylsulfilimines (X) in Diels-Alder reactions with acyclic and cyclic dienes, 1-aza-1,3-butadienes, furan and 1,3-oxazoles are briefly considered. Isothiazol-3(2H)-one 1,1-dioxides (I), 3-alkoxy- and 3-dialkylaminoisothiazole 1,1-dioxides (II) also readily undergo 1,3-dipolar cycloaddition with diazoalkanes, azides, nitrile imines, nitrile oxides, oxazolones and muenchnones. This reaction is characterized by high degree of regioselectivity.