Regular Issue

Vol. 22, No. 7, 1984

21 data found. 1 - 21 listed
Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1473 - 1476
Published online:
DOI: 10.3987/R-1984-07-1473
Novel Bicyclic Selenuranes: Syntheses and Properties of 10-Chloro-10,9-epoxyethanoselenoxanthenes and Their Related Compounds

Tadashi Kataoka, Kiminori Tomimatsu, Katsutoshi Tanaka, Hiroshi Shimizu, and Mikio Hori*

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


The novel stable bicyclic selenuranes, 10-chloro(or bromo)-10,9-epoxyethano (or epoxymethano)selenoxanthenes and 10-chloro(or bromo)-9,10-epoxy-9-phenylselenoxanthene were synthesized. Some properties of these selenuranes are also described.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1477 - 1481
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DOI: 10.3987/R-1984-07-1477
Modification of α-Santonin VIII. Chlorination of α-Santonin Derivatives

Yasuo Fujimoto,* Hiroyuki Matabe, Kazushige Nishikawa, Takeshi Shimizu, and Takashi Tatsuno

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan


Chlorination of α-santonin derivatives with iodobenzene dichloride or dichlorourethane under photo-irradiation has been investigated. The structures of the chlorides were elucidated by their 1H-NMR data including decoupling experiments.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1483 - 1487
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DOI: 10.3987/R-1984-07-1483
Studies in the Stereospecific Synthesis of Sesbanimide. Synthesis of 4-Saccharidalglutarimides

Martin J. Wanner, Gerrit-Jan Koomen, and Upendra K. Pandit*

*Organic Chemistry Department, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands


Suitably protected saccharidyl aldehydes are converted into the corresponding glutarimide derivatives via a two-step sequence involving reactions with (a) Ph3P=CHCOOMe and (b) CH2(CONH2)COOR.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1489 - 1492
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DOI: 10.3987/R-1984-07-1489
A Simple Route to Spiroketals via Alkylation of Dihydropyran

Roger Amouroux*

*Laboratoire de Chimie Organique Physique et Synthétique, Associe au CNRS, Université Claude Bernard, Lyon 1, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France


3,4-Dihydro-2H-pyran was alkylated, via its 2-lithio derivative, with several O-protected β- or γ-iodo alcohols in excellent yields. Acidic treatment of the resultant 2-substituted dihydropyrans produced both the deprotection of the hydroxyl group and the cyclization to spiroketals.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1493 - 1496
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DOI: 10.3987/R-1984-07-1493
Direct Regioselective Vinylation of Indoles Using Palladium (II) Chloride

Yasuoki Murakami,* Yuusaku Yokoyama, and Tsuyoshi Aoki

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Direct regioselective vinylation at C3-position of ethyl indole-2-carboxylate, its N-benzyl derivative, and N-benzylindole with various conjugated olefins was accomplished in the presence of palladium (II) chloride and acetate salt in good to moderate yields.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1497 - 1500
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DOI: 10.3987/R-1984-07-1497
Novel Ring Contractions of 2,7-Dihydro-3,6-diphenyl-1,4,5-thiadiazepine via a Halogenation-dehalogenation Process

Kichinosuke Kamata and Otohiko Tsuge*

*Kurume Technical College, Komorinocho 1232, Kurume, Fukuoka 830-0001, Japan


2,7-Dihydro-3,6-diphenyl-1,4,5-thiadiazepine undergoes novel ring contractions via a halogenation-dehalogenation process in methanol, giving sulfur-containing five-membered cyclic compounds: this result is a great contrast to the ring contraction with extrusion of sulfur reported previously.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1501 - 1504
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DOI: 10.3987/R-1984-07-1501
Photolysis and Thermolysis of Quinolyl and Isoquinolyl Azides in Ethanethiol

Hiroyuki Sawanishi, Toyoko Hirai, and Takashi Tsuchiya*

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


3-Quinolyl azides (8), upon either irradiation or heating in ethanethiol, gave 3-amino-4-ethylthioquinolines (9), presumably via a radical process. Similarly, 4-isoquinolyl azides (11) gave 3-ethylthio- (12) and/or 1-ethylthio-4-aminoisoquinolines (13), and 8-quinolyl azide (17) gave 7-ethylthio- (18) and 5-ethylthio-8-aminoquinoline (19), while 4-quinolyl azides (15) gave only 8-aminoquinolines (16).

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1505 - 1508
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DOI: 10.3987/R-1984-07-1505
A Novel Reaction of Hydroxylamine with Substituted 7-Amino-8-quinolinols

John H. Musser*

*Research and Development Division, Revlon Health Care Group, Tuckahoe, New York 10707, U.S.A.


A novel reaction of hydroxylamine with substituted 7-amino-8-quinolinols is reported.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1509 - 1512
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DOI: 10.3987/R-1984-07-1509
Synthesis of Methylene (R)-6-Acetonylidene-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-carboxylete Pivalate

Solange Adam*

*Pharma Division, Pharma Preclinical Research & Development, F.Hoffmann-La Roche Ltd., Grenzacherstrasse 124, CH-4070 Basel, Switzerland


Methylene (Z)-6-acetonylidenepenicillanate pivalate (1b) a powerful inhibitor of β-lactamases, is converted efficiently into the title compound.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1513 - 1518
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DOI: 10.3987/R-1984-07-1513
Autoxidation of Nitrogen Heterocycles. 1. Ultraviolet Spectra of Alkylpyrroles. Evidence for a Molecular Association Complex between Oxygen and 2,5-Dimethylpyrrole in Non-polar Media

John V. Cooney* and Robert N. Hazlett

*Chemsitry Division, Naval Research Laboratory, Washington, D. C. 20375, U.S.A.


Ultraviolet spectroscopy indicates that molecular oxygen associates extensively and reversibly with 2,5-dimethylpyrrole in hydrocarbon solution. The formation of such a molecular association complex is believed to be the first step in the principal autoxidation sequence for this pyrrole.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1519 - 1522
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DOI: 10.3987/R-1984-07-1519
Addition of Trimethylsilyl Enol Ethers to Quinolinium Salts: A Facile Synthesis of Methyl 2-(2-Oxoalkyl)-1,2-dihydroquinoline-1-carboxylates and Their Cyclization

Kin-ya Akiba,* Toshifumi Kobayashi, and Yohsuke Yamamoto

*Department of Chemistry, Faculty of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan


The addition of trimethylsilyl enol ethers (2) to 1-alkoxycarbonylquinolinium salts (1) afforded a mixture of 1-alkoxycarbonyl-2-(2-oxoalkyl or alkoxycarbonyl)-1,2-dihydroquinolines (3) and the corresponding 1,4-dihydroquinolines (4) in high total yield (85-99%). The regioselectivity ( 3/4 = 2.3-19 ) was examined carefully. The easily separated main products (3) were treated with sodium hydride to give the corresponding benzo[c]quinolizine derivatives (5).

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1523 - 1526
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DOI: 10.3987/R-1984-07-1523
Synthesis and Ylidic Properties of 1-Arylthiabenzene 1-Oxides

Haruo Matsuyama,* Hiroyuki Takeuchi, and Yukio Okutsu

*Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan


1-Arylthiabenzene 1-oxides were prepared by condensation reactions between arylmethyloxosulfonium methylides and 1,3-diphenyl-2-propyn-1-one (or 2-acetylcyclohexanone). An ylidelike bonding structure is proposed for the 1-arylthiabenzene 1-oxides.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1527 - 1530
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DOI: 10.3987/R-1984-07-1527
General Synthesis of 1,4-Dithiins from Diketo Sulfides

Juzo Nakayama,* Hideji Motoyama, Haruki Machida, Masahiro Shimomura, and Masamatus Hoshino

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan


A variety of 1,4-dithiins are prepared in good yields by treatment of diketo sulfides (readily obtainable from α-haloketones and sodium sulfide) with phosphorus pentasulfide or Lawesson‘s reagent.

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Communication | Regular issue | Vol 22, No. 7, 1984, pp. 1531 - 1535
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DOI: 10.3987/R-1984-07-1531
A Convenient Synthesis of Novel 3-Quinoxalinyl-1,5-benzodiazepines. Stable Tautomers in 1,5-Benzodiazepin-2-one Ring System

Yoshihisa Kurasawa,* Jun Satoh, Mie Ogura, Yoshihisa Okamoto, and Atsushi Takada

*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan


Various 3-quinoxalinyl-1,5-benzodiazepines (3,4,6,7) were prepared via the ring transformation of 3-(N,N-dimethyl-carbamoyl)furo[2,3-b]quinoxaline hydrochloride (1). The hydrochlorides 3 and 7 are the tautomers of the N1,- or N5-H form and C3-H form, respectively, which are stable in solid and solution.

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Report | Regular issue | Vol 22, No. 7, 1984, pp. 1537 - 1544
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DOI: 10.3987/R-1984-07-1537
Synthesis of the Natural Coumarinolignoids Propacin and Cleomiscosin A and B. An Empirical Spectroscopic Method to Distinguish Regioisomers of Natural Benzodioxane Lignoids

Anna Arnoldi, Alberto Arnone, and Lucio Merlini*

*Istituo di Biochimica Generale, Università digli Studi di Milano, Via Venezian 21, 20133 Milano, Italy


The synthesis of the title coumarinolignoids by Ag2O oxidation of fraxetin and isoeugenol or coniferyl alcohol is reported. A simple diagnostic method based on 13C nmr spectra is proposed to distinguish regioisomers of natural benzodioxane lignoids.

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Report | Regular issue | Vol 22, No. 7, 1984, pp. 1545 - 1554
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DOI: 10.3987/R-1984-07-1545
N,N-Dimethylchloroformiminium Chloride in the Synthesis of Heterocyclic Compounds. The Synthesis of N-Heteroarylformatidine Hydrochlorides, Oxazolo[5,4-d]pyrimidines, Fused Imidazoles and Other Systems

Branko Stanovnik,* Oliver Bajt, Branko Belcic, Bozidar Koren, Marija Prhavc, Anton Stimac, and Miha Tisler

*Department of Chemistry, E. Kardelj University, Murnikova 6, 61000 Ljubljana, Slovenia


N,N-Dimethylchloroformiminium chloride (DCFC) was used for preparation of N-heteroarylformamidine hydrochlorides (2), fused oxazoles (4), imidazoles (6, 8) and thiazoles (10). DCFC is advantageous in those cases in which the undesired further methylation of NH, OH, and SH groups could occur by using N,N-dimethylformamide dimethyl acetal (DMFDMA).

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Report | Regular issue | Vol 22, No. 7, 1984, pp. 1555 - 1559
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DOI: 10.3987/R-1984-07-1555
Aminopyrimidines and Derivatives. XVI. Synthesis of 7-Grycosyl-amino-oxazolo(5,4-d)pyrimidines

A. Sánhcez Rodrigo, C. Rodriguez Melgarejo, M. Rodriguez Alonso, M. Nogueras Montiel, M. Melgarejo Sampedro,* and R. Asenjo Asenjo

*Dept. Química Orgánica, Colegio Universitario de Jaén, Universidad de Granada, 23071 Jaén, Spain


Treatment of 5-amino-4-glycosylamino-6-oxo-pyrimidines 1 with acetic anhydride under reflux has led to 2-methyl-7-glycosylamino-oxazolo[5,4-d]pyrimidines 2.

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Report | Regular issue | Vol 22, No. 7, 1984, pp. 1561 - 1564
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DOI: 10.3987/R-1984-07-1561
Studies in Cycloaddition Reactions: Synthsis of Novel 1,3-Diaryl-1H,9H-tetrazolo[1,2-a]benzotriazoles

Eltepu Sayanna, Revannuru Venkatachaliah Venkataratnam,* and Gopalakrishna Thyagarajan

*Division of Organic Chemistry, Regional Research Laboratory, Hyaderabad 500 007, India


1,3-Diphenyl derivatives of the new heterocyclic system 1H,9H-tetrazolo[1,2-a]benzotriazole have been prepared by the 1,3-dipolar cycloaddition reaction of nitrileimines to benzotriazole. 1-(N-phenylbenzhydrazidoyl)-benzotriazoles are also formed simultaneously in the reaction and have been found to be stable and not convertible into the respective tetrazolobenzotriazoles. The tetrazolobenzotriazoles do not decompose into the benzhydrazidoyl benzotriazoles. Methylation of benzotriazole inhibits the addition of the dipole.

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Report | Regular issue | Vol 22, No. 7, 1984, pp. 1565 - 1570
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DOI: 10.3987/R-1984-07-1565
Reactions with Indole Derivatives, XLIX. The Stereoselective Total Synthesis of D-Norvincamine

Hiromitsu Takayama and Ekkehard Winterfeldt*

*Institut fur Organische Chemie, Universität Hannover, Schneiderberg 1 B, D-30167 Hannover, Germany


A stereoselective synthesis of D-norvincamine (1) is described starting from cyclopropane derivative (2), via isoeburnamonine (6).

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Report | Regular issue | Vol 22, No. 7, 1984, pp. 1571 - 1589
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DOI: 10.3987/R-1984-07-1571
The Chemistry of Furazans

Wanda Sliwa*

*Department of Organic Chemistry, Pedagogical University, Al. Armii Krajowej 13/15, 42-201 Czestochowa, Poland


Syntheses, chemical reactivity and physical properties of furazans are presented.

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Report | Regular issue | Vol 22, No. 7, 1984, pp. 1591 - 1612
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DOI: 10.3987/R-1984-07-1591
Modified Polonovski Reaction, a Versatile Synthetic Tool

Mauri Lounasmaa* and Ari Koskinen

*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland


Recent synthetic applications of the modified Polonovski reaction are reviewed. In particular, the mechanistic consequences of the reaction are discussed.

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21 data found. 1 - 21 listed