Regular Issue

Vol. 57, No. 10, 2002

18 data found. 1 - 18 listed
Communication | Regular issue | Vol 57, No. 10, 2002, pp. 1777 - 1780
Published online:
DOI: 10.3987/COM-02-9547
Bifunctionalized Allenes. Part V. 3-Sulfinyl-2,5-dihydro-1,2λ5-oxaphosphol-2-ones and 3-Phosphoryl-1,2λ4-oxathiol-2(5H)-ones from 1-Sulfinyl-substituted Phosphorylated Allenes

Valerij Ch. Christov* and Boris Prodanov

*Department of Chemistry, University of Shoumen, BG-9700 Shoumen, Bulgaria


3-Sulfinyl-2,5-dihydro-1,2λ5-oxaphosphol-2-ones (3) and 3-phosphoryl-1,2λ4-oxathiol-2(5H)-ones (4) were synthesized in good yields via electrophile-induced cyclization reactions of 1-sulfinyl-substituted phosphorylated allenes (1) and (2). Bromination of dimethyl 1-sulfinyl-1,2-alkadiene-1-phosphonates (1) led to formation of 4-bromo-3-sulfinyl-2,5-dihydro-1,2λ5-oxaphosphol-2-ones (3), while the reaction with methyl 1-diphenylphosphoryl-1,2-alkadiene-1-sulfinates (2) afforded 4-bromo-3-diphenylphosphoryl-1,2λ4-oxathiol-2(5H)-ones (4).

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Communication | Regular issue | Vol 57, No. 10, 2002, pp. 1781 - 1786
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DOI: 10.3987/COM-02-9564
Palladium Catalyzed Double Substitution Reactions of Iodophenol and Iodoaniline Derivatives with Homo-conjugated Compounds to Form Cyclic Ether and Cyclic Amines through Homo-conjugated Interaction

Katsuhiro Saito,* Katsuhiko Ono, Makiko Sano, Shingo Kiso, and Toshihumi Takeda

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Palladium(II) acetate catalyzed double substitution reaction of a bicyclo[2.2.2]octadiene derivative (1) with o-substituted iodobenzenes afforded six membered cyclic compounds (3b and 3c) via a homo-conjugation type interaction accompanied by a five-membered cyclic compound (4a). On the other hand, a similar type of reaction but using a bicyclo[2.2.1]heptadiene derivative (5) formed only the corresponding five-membered cyclic compound (6a).

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Communication | Regular issue | Vol 57, No. 10, 2002, pp. 1787 - 1792
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DOI: 10.3987/COM-02-9567
Two Novel 6-Hydroxyanthocyanins in the Flowers of Alstroemeria ‘Westland’

Fumi Tatsuzawa,* Norio Saito, Naho Murata, Koichi Shinoda, Atsushi Shigihara, and Toshio Honda

*Hokkaido Junior College, Takushoku University, Fukagawa, Hokkaido 074-8585, Japan


Two novel 6-hydroxydelphinidin glycosides were isolated from the red-purple flowers of Alstroemeria ‘Westland’ along with ten known anthocyanins. These novel pigments were determined to be 6-hydroxydelphinidin 3-O-β-D-glucoside and 6-hydroxydelphinidin 3-O-[6-O-(malonyl)-β-D-glucoside] by spectral and chemical methods. The ten known pigments were also identified as cyanidin 3-glucoside, delphinidin 3-glucoside, 6-hydroxycyanidin 3-glucoside, cyanidin 3-rutinoside, delphinidin 3-rutinoside, 6-hydroxycyanidin 3-rutinoside, 6-hydroxydelphinidin 3-rutinoside, cyanidin 3-malonylglucoside, delphinidin 3-malonylglucoside, and 6-hydroxycyanidin 3-malonylglucoside, respectively.

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Communication | Regular issue | Vol 57, No. 10, 2002, pp. 1793 - 1797
Published online:
DOI: 10.3987/COM-02-9570
Syntheses of (4R, 5S)- and (4S, 5R)-Muricatacins, and (4S, 5R)-Aza-Muricatacin, Unnatural Analogues of the Annonaceous Acetogenin

Hiroyuki Konno,* Naoki Hiura, and Moegi Yanaru

*Department of Biological Science and Technology, Faculty of Engineering, University of Tokushima, Minamijosanjima-cho, Tokushima 770-0814, Japan


(4R, 5S)- and (4S, 5R)-Muricatacins, and (4S, 5R)-aza-muricatacin, unnatural analogues of the Annonaceous acetogenin, were prepared from (-)-muricatacin via Mitsunobu inversion or Weinreb amidation as the key step.

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Paper | Regular issue | Vol 57, No. 10, 2002, pp. 1799 - 1806
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DOI: 10.3987/COM-02-9521
N-Arylation by Aryl Isocyanates as a General Reaction: Useful Route to Disubstituted S,N-Diarylisothioureas

Alan R. Katritzky,* Xiaohong Cai, Vladimir Y. Vvedensky, Boris V. Rogovoy, Behrouz Forood, and Normand Hebert

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


N-Arylation of guanidines, isoureas and isothioureas by aryl isocyanates is demonstrated to have generality. Novel N′-arylations of S-arylisothioureas (16) with aryl isocyanates provide a new general route to biologically active S,N′-diarylisothioureas (13). Formation of (13) is explained as [2+2] cycloaddition of isoureas (16) to isocyanates followed by elimination of HNCO.

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Paper | Regular issue | Vol 57, No. 10, 2002, pp. 1807 - 1830
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DOI: 10.3987/COM-02-9529
Stereoselective Synthesis of C-6 Substituted Pipecolic Acid Derivatives. Formal Synthesis of (+)-Indolizidine 167B and (+)-Indolizidine 209D

Sylvie Carbonnel and Yves Troin*

*Laboratoire de Chimie des Hétérocycles et des Glucides, EA 987, Ecole Nationale Supérieure de Chimie de Clermont-Ferrand, Université Blaise Pascal, BP187, 63174 Aubiére Cedex, France


C-6 Substituted pipecolic acid derivatives were synthesized through two different pathways. The synthetic potential of each route was demonstrated by the formal synthesis of indolizidine Dendrobates alkaloids.

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Paper | Regular issue | Vol 57, No. 10, 2002, pp. 1831 - 1840
Published online:
DOI: 10.3987/COM-02-9551
Synthesis of Some Thiophene-fused Azepino[5,4,3-cd]indoles

Basem A. Moosa, Kayed A. Abu Safieh, and Mustafa M. El-Abadelah*

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan


Interaction of indolylzinc chloride with 2-chloro-3-nitrothiophene gave 3-(3-nitrothien-2-yl)indole (7) which was converted, via reduction followed by acylation, into 3-(3-acylaminothien-2-yl)indoles (9a-c). Cyclization of 9a-c induced by phosphorus oxy-chloride under Bischler-Napieralski reaction conditions, took place regioselectively at the indolic C-4 locus to furnish the respective thieno[2’,3’ : 6,7]azepino[5,4,3-cd]indoles (3a-c).

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Paper | Regular issue | Vol 57, No. 10, 2002, pp. 1841 - 1850
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DOI: 10.3987/COM-02-9561
Regioselective Preparation of Pterin 6-Triflate and Its Application to 6-Substituted Pterin Synthesis

Masato Kujime, Kazunari Kudoh, and Shizuaki Murata*

*Graduate School of Environmental Studies, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


4-Butoxypteridine 6-triflate is prepared selectively from 4-butoxypteridine 8-oxide by a reaction with trifluoromethanesulfonic anhydride, and the triflate group can be replaced by various nucleophiles with functional groups.

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Paper | Regular issue | Vol 57, No. 10, 2002, pp. 1851 - 1868
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DOI: 10.3987/COM-02-9585
About the Factors Which Govern the Ring-Opening of α-Lactams with Primary Amines: II. The Relative Basicity of the Amine

Victor Cesare,* Tony Taldone, and István Lengyel

*Department of Chemistry, St. John’s University, 8000 Utopia Parkway, Jamaica, New York 11439, U.S.A.


The ring-opening reaction of four stable α-lactams, 1-(1-adamantyl)-3,3-di-methylaziridinone (1a), 3-(1-adamantyl)-1-triphenylmethyl-aziridinone (1d), 3-tert-butyl-1-triphenylmethylaziridinone (1e), and 1-(1-adamantyl)-3-tert-butylaziridinone (1g) with some substituted benzylamines and other selected primary amines is described. It emerges from the experimental results that the relative basicity of the amine is a decisive factor in determining regioselectivity in the ring-opening.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1869 - 1879
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DOI: 10.3987/COM-02-9478
1H NMR Evidence of C–H---O, C–H---N and C–H---Cl Hydrogen Bonds in New Thiazole Derivatives

Francisco Sánchez-Viesca* and Martha Berros

*Faculty of Chemistry, Postgrade Division, National Autonomous University, University City, 04510, Mexico, D.F.


A comparative study of the chemical shift differences observed in the 1H NMR spectra of a series of fifteen new polysubstituted 4-aryl- and 2,4-diaryl thiazoles permitted us to establish two groups of rotamers. Some present paramagnetic shifts due to intramolecular weak hydrogen bonding and this was confirmed by experiments “at infinite dilution”, single crystal X-Ray studies, NOESY and HMBC experiments.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1881 - 1890
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DOI: 10.3987/COM-02-9524
Improved Synthesis of N-Substituted 2,3-Pyridinedicarboximides with Microwave Irradiation

María M. Blanco, Gustavo J. Levin, Celia B. Schapira, and Isabel A. Perillo*

*Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113) Buenos Aires, Argentina


The microwave-induced synthesis of N-substituted 2,3-pyridinedicarboximides (1) by means of two different approaches is presented. One involves direct N-alkylation of quinolinimide (2) (Method A) and the other, dehydrative condensation of quinolinic anhydride (4) and amines (Method B). Reactions resulted highly accelerated, with improved yields in relation to those obtained by conventional heating. The scope and limitations of each method and its variants are discussed.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1891 - 1896
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DOI: 10.3987/COM-02-9531
Fluorinated Heterocyclic Compounds. Synthesis of 5-Amino-, 5-N-Alkylamino-, and 5-N,N-Dialkylamino-3-perfluoroheptyl-1,2,4-oxadiazoles

Silvestre Buscemi,* Andrea Pace, Ivana Pibiri, and Nicolò Vivona

*Dipartimento di Chimica Organica, Università degli Studi di Palermo, Viale delle Scienze-Parco d’Orleans II, I-90128 Palermo, Italy


The synthesis of 5-amino-, 5-N-alkylamino-, and 5-N,N-dialkylamino-3-perfluoroheptyl-1,2,4-oxadiazoles has been realized with very good yields by ammonolysis or aminolysis of the 3-perfluoroheptyl-5-trichloromethyl-1,2,4-oxadiazole with ammonia, primary or secondary aliphatic amine. Some comments on the absorption spectra of fluorinated aminooxadiazoles are reported.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1897 - 1900
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DOI: 10.3987/COM-02-9532
A Photochemical Route to Dibenzonaphthyrones

Yvette A. Jackson* and Karla-Sue C. Marriott

*Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica, West Indies


Irradiation of 2-methyl 3-phenyl 5,6-dimethoxy-1-benzofuran-2,3-dicarboxylate (5) gave 2,3-dimethoxybenzopyrano[4,3-c]benzopyran-5,11-dione (1b).

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1901 - 1906
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DOI: 10.3987/COM-02-9544
Prenylated Isoflavones from Derris scandens

Mayuree Chuankamnerdkarn,* Somyote Sutthivaiyakit, Nopporn Thasana, and Somchai Pisutjaroenpong

*Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand


3′-Formylalpinumisoflavone (1), and 2-(1-hydroxy-1-methylethyl)-3-hydroxy-2,3-dihydrofuranoalpinumisoflavone (2) were isolated from the stem of Derris scandens along with five known isoflavones. The two new compounds were characterised by extensive use of high resolution NMR spectroscopy. Senegalensin (3) was reported here for the first time in D. scandens.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1907 - 1914
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DOI: 10.3987/COM-02-9549
Synthesis of Dihydrothiophene Derivatives as Metabolites of Esonarimod

Toshiya Noguchi,* Akira Onodera, Kazuyuki Tomisawa, and Sadakazu Yokomori

*Process Chemistry Latoratory, Medicinal Research Laboratories, Taisho Pharmaceutical Co., Ltd., 1-403 Yoshino-Cho, Saitama-city, Saitama 330-8530, Japan


Three compounds with a dihydrothiophene ring were synthesized as authentic samples to analyze human metabolites of Esonarimod, which has been developed as a new antirheumatic drug.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1915 - 1918
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DOI: 10.3987/COM-02-9557
A New Route to Benzo[b]xanthene-6,11,12-trione Derivatives Based on the Photoinduced o-Hydroxybenzoylation of 1,4-Naphthoquinone

Kazuhiro Kobayashi,* Akihiro Matsunaga, Masaaki Mano, Osamu Morikawa, and Hisatoshi Konishi

*Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


A two-step procedure for the synthesis of the title xanthenequinone derivatives is described. The procedure involves the photoinduced acylation of 1,4- naphthoquinone with 2-hydroxybenzaldehydes, followed by treatment with Ag2O.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1919 - 1933
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DOI: 10.3987/COM-02-9558
Synthesis of Heteromacrocycles Containing 2-Imino-5-mercapto-2,3-dihydro-1,3,4-thiadiazoles as a Subunit

Nam Sook Cho,* Jin Gap Oh, Hye Jeong Hwang, Jin-Guy Kim, and Il-hwan Suh

*Department of Chemistry, College of Natural Sciences, Chungnam National University, Taejon 305-764, Korea


Macrocycles containing two 2-imino-5-mercapto-2,3-dihydro-1,3,4-thiadiazole subunits linked to the 3- and 5-positions of the heterocycle unit were prepared by regiospecific alkylation of 5-amino-2,3-dihydro-1,3,4-thiadizole-2-thione and 2-acetylamino-5-alkylthio-1,3,4-thiadizoles, respectively. The structures of the macrocycles were established from 1H and 13C NMR, IR, MS spectrometries and elemental analyses. Moreover, the structure of the macrocycle 1,5-[5,5’-(1,3-phenylenedimethylenedithio)bis(2,3-dihydro-2-acetylimino-1,3,4-thiadiazol-2-yl)]-3-oxapentane (4b) was supported by X-Ray crystallography.

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Note | Regular issue | Vol 57, No. 10, 2002, pp. 1935 - 1946
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DOI: 10.3987/COM-02-9577
Synthesis of p-Phenylene-Vinylene-Thienylene Oligomers

Cuihua Xue and Fen-Tair Luo*

*Institutue of Chemistry, Academia Sinica, Academia Sinica, Nankang, Taipei,11529, Taiwan, R.O.C.


The preparation of alkoxylated phenylene-vinylene-thienylene oligomers with and without cyano substituents at the olefin moieties and their spectroscopic measurements are presented. Both thiophene ring and cyano groups may induce red shift in their absorption spectra.

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18 data found. 1 - 18 listed