Special Issue

30th Anniversary's Special Issues, Vol. 61, No. 1, 2003

69 data found. 61 - 69 listedFirst Previous
Note | Special issue | Vol 61, No. 1, 2003, pp. 541 - 550
Published online: 4th August, 2003
DOI: 10.3987/COM-03-S18
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.


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.

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Note | Special issue | Vol 61, No. 1, 2003, pp. 551 - 555
Published online: 4th August, 2003
DOI: 10.3987/COM-03-S28
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


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.

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Note | Special issue | Vol 61, No. 1, 2003, pp. 557 - 561
Published online: 6th October, 2003
DOI: 10.3987/COM-03-S31
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


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.

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Note | Special issue | Vol 61, No. 1, 2003, pp. 563 - 567
Published online: 2nd October, 2003
DOI: 10.3987/COM-03-S39
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


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.

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Note | Special issue | Vol 61, No. 1, 2003, pp. 569 - 579
Published online: 11th August, 2003
DOI: 10.3987/COM-03-S49
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


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.

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Note | Special issue | Vol 61, No. 1, 2003, pp. 581 - 586
Published online: 22nd September, 2003
DOI: 10.3987/COM-03-S53
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


Syntheses of novel spiro bis-pyridinium and bis-quinolinium salts have been achieved in three steps via intramolecular N-alkylation.

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Note | Special issue | Vol 61, No. 1, 2003, pp. 587 - 592
Published online: 2nd October, 2003
DOI: 10.3987/COM-03-9887
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.


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.

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Review | Special issue | Vol 61, No. 1, 2003, pp. 593 - 637
Published online: 14th October, 2003
DOI: 10.3987/REV-03-SR1
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


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.

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Review | Special issue | Vol 61, No. 1, 2003, pp. 639 - 661
Published online: 14th November, 2003
DOI: 10.3987/REV-03-SR2
[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


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.

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