Regular Issue

Vol. 19, No. 9, 1982

28 data found. 1 - 28 listed
Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1565 - 1569
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DOI: 10.3987/R-1982-09-1565
A Synthesis of N-(4’-Quinazolon-3’-yl)-2-pyridinecarboxamidines and Their Conversion into 1,2,4-Triazoles

Katsuhiko Nagahara and Atsushi Takada

*School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan


Treatment of N-(2’-aminobenzoyl)-2-pyridylamidrazone (1) with ethoxymethylenemalononitrile (EMMN) and ethyl ethoxymethylenecyanoacetate (EMCA) or ortho esters afforded the corresponding N-(2’-alkyl-4’-quinazolon-3’-yl)-2-pyridinecarboxamidines (2). Futhermore, treatment of 2 with ethanolic hydrochloric acid caused the ring transformation to give corresponding 5-alkyl-3-(2’-pyridyl)-1H-1,2,4-triazoles (3).

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1571 - 1574
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DOI: 10.3987/R-1982-09-1571
A Facile Syntheses of Thiazolidin-5-ones and Their Structural Assignment

Tadashi Okawara, Kentaro Nakayama, and Mitsuru Furukawa

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan


The reaction of 1,3-disubstituted thioureas(I) with α-haloacyl halides(II) was found to afford thiazolidin-5-ones(IV) in 5% sodium hydroxide-dichloromethane in the yields of 34-89%. The structures of IV were discussed in details.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1575 - 1579
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DOI: 10.3987/R-1982-09-1575
Catecholic Ion Formation from 5-Substituted 2,2-Dimethyl-1,3-benzodioxoles Molecular Ions

Pietro Traldi, Umbreto Vettori, Antonio Maccioni, and Gianni Podda

*Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venzian 21, 20133 Milano, Italy


The presence of catecholic ions in the mass spectra of 5-substituted 2,2-dimethyl-1,3-benzodioxoles is proved to originate from a primary decomposition process analogous to that observed for 2,2-disubstituted 1,3-benzoxathioles.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1581 - 1584
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DOI: 10.3987/R-1982-09-1581
Galangustin, a New Flavone from Galeopsis angustifolia

Giuseppe Savona, Franco Piozzi, Benjamin Rodriguez, and Orietta Servettaz

*Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy


Galangustin has the structure of 5,7-dihydroxy-8,4’-dimethoxyflavone.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1585 - 1586
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DOI: 10.3987/R-1982-09-1585
Stereochemistry of Silychristin, Mild Dehydrogenation of Flavononols

Antonio Zanarotti

*CNR, Centro Studio Sostanze Organiche Naturali, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133 Milano, Italy


3-Hydroxyflavanones can be quantitatively dehydrogenated by air in pyridine to 2,3-dehydro derivatives. The reaction has been performed on silychristin (1) in order to remove the chirality at the flavanonol ring and to allow the assignment of the stereochemistry of the dihydrobenzofuran ring as 2’R,3’S

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1587 - 1590
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DOI: 10.3987/R-1982-09-1587
The Structure of (+)-Isocorynoline

Mark Cushman, Aziz Abbaspour, and Yash Pal Gupta

*Department of Medicinal Chemistry and Molecular Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, 1333 Robert E. Heine Pharmacy Building, West Lafayette IN 47907, U.S.A.


(±)-14-Epicorynoline (5) and (±)-13-epicorynoline (14) are synthesized from a common intermediate 13. The identity of (+)-isocorynoline with (+)-14-epicorynoline is also demonstrated.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1591 - 1593
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DOI: 10.3987/R-1982-09-1591
On the Structure of Cataline

Luis Castedo, Ricardo Riguera, Javier Sardina, Severino García-Blanco, and Isabel Fonseca

*Facultad de Química y Sección de Alcaloides, Deparamento de Química Orgánica, C. S. I. C., Santiago de Compostela, Spain


A pmr study of the 4-hydroxyaporphine cataline in the presence of Eu(fod)3 further supports structure I proposed for this alkaloid. This was confirmed by an X-Ray analysis.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1595 - 1596
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DOI: 10.3987/R-1982-09-1595
Ring Transformation of Heterocycles via N-Imide Intermediates: From Nicotine to Hexahydropyrido[3,4-b]1,2-diazocine

Yasumitsu Tamura, Masayoshi Tsunekawa, Hiroyuki Ikeda, and Masazumi Ikeda

*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


Treatment of the N-amino derivative of nicotine with sodium amide in liquid ammonia gave 2-methylhexahydropyrido[3,4-b]-1,2-diazocine.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1597 - 1604
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DOI: 10.3987/R-1982-09-1597
Synthesis of New Oxapenams and Carbapenams

Kapa Prasad and Peter Stütz

*Sandoz Research Institute, A-1235 Vieena, Austria


Diazoketones derived from 4-thioazetidinon-1-yl-acetic acids, on metal-catalysed decomposition, gave either carbapenams and/or oxapenams depending upon the nature of the substituent present on the thio function. Synthesis of a novel oxapenam carboxylic acid 16 which exhibited potent β-lactamase inhibitory properties comparable to clavulanic acid is described.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1605 - 1607
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DOI: 10.3987/R-1982-09-1605
A Novel and Stereoselective Synthesis of cis-1,8-H-1-Hydroxypyrrolizidine

Tatsushi Ohsawa, Masataka Ihara, Keiichiro Fukumoto, and Tetsuji Kametani

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


The title compound was synthesized through a regioselective introduction of allyl group at the C2 position of the 3-oxopyrrolidine derivative (2) by [3,3] sigmatropic rearrangement and an amino cyclization via the episulfonium intermediate (8) by key steps.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1609 - 1614
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DOI: 10.3987/R-1982-09-1609
Reactions of N-Phenyl-β-aminoacohols with Acetylenic Esters

Otohiko Tsuge, Koji Oe, and Toshiyuki Ohnishi

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


erythro-1,2-Diphenyl-2-phenylaminoethanol 1 reacted with dimethyl acetylenedicarboxylate (DMAD) in refluxing benzene to give the cis-Michael adduct, whereas the same reaction in methanol at room temperature afforded a mixture of the Michael adduct and tetrahydro-1,4-oxazepin-7-one derivative. Although threo-isomer 4 was less reactive than 1, 4 reacted with DMAD in methanol or in the presence of triethylamine in benzene at room temperature to give the cis- or trans-Michael adduct, respectively. Photochemical and acid-catalyzed transformations of the Michael adducts to 1,4-oxazepine and oxazolidine derivatives are also described. The reaction of cis-1-hydroxy-2-phenylaminoacenaphthene 10 with DMAD gave the trans-Michael adduct, which on heating in acetic acid was converted into the corresponding oxazolidine. On the other hand, 1, 4, and 10 reacted with methyl phenylpropiolate in the presence of triethylamine in refluxing xylene afforded the corresponding oxazolidin-2-ones.

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Communication | Regular issue | Vol 19, No. 9, 1982, pp. 1615 - 1617
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DOI: 10.3987/R-1982-09-1615
Structure of Arcapillin, an Antihepatotoxic Principle of Artemisia capillaris Herbs

Yoshinobu Kiso, Keiko Sasaki, Yoshiteru Oshima, and Hiroshi Hikino

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


In view of the observation that a methanol extract of Artemisia capillaris herbs has shown intense suppressive activity in carbon tetrachloride-induced liver lesion in mice, the extract has been fractionated by monitoring the hepatotoxic activity to furnish the known flavonol, eupatolitin (III), and a new flavone, arcapillin, as the liver-protective principles. The structure of arcapillin has been elucidated as that represented by formula I on the basis of chemical and physical data.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1619 - 1622
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DOI: 10.3987/R-1982-09-1619
Oxidation of 3-Methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline with m-Chloroperbenzoic Acid

Yoshihisa Kurasawa, Yujiro Moritaki, and Atsushi Takada

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


The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline (Ia) with m-chloroperbenzoic acid gave 3-(1-hydroxy-1-methoxycarbonyl)methylene-2-oxo-1,2,3,4-tetrahydroquinoxaline and 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline. The equilibrium between the tetrahydro form (Ia type) and the dihydro form (Ib type) was exhibited, together with the 1H-NMR data.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1623 - 1626
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DOI: 10.3987/R-1982-09-1623
Addition Reactions of Condensed Azole Derivatives with Dimethyl Acetylenedicarboxylate III

Norio Kawahara, Takako Nakajima, Tsuneo Ito, and Haruo Ogura

*Hokkaido College of Pharmacy, 7-1 Katsuraoka-cho, Otaru 047-02, Japan


Benzimidazole derivatives (1) reacted with dimethyl acetylenedicarboxylate (DMAD) in alcoholic solvents at room temperature to afford three kinds of addition products; tricyclic compounds (3 and 6), hydration product (4) and solvent adduct (2).

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1627 - 1632
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DOI: 10.3987/R-1982-09-1627
Propellanes. LXV. Dithia[3.3.n]propellanes, Their Metal Salt Complexes, Sulfilimines and Sulfoxides

Ishai Sataty, Michael Peled, and David Ginsburg

*Department of Chemistry, Israel Institute of Technology, Haifa 32000, Israel


The structures of the title compounds and those of various derivatives have been studied.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1633 - 1635
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DOI: 10.3987/R-1982-09-1633
13C NMR Spectroscopy of Substituted Imidazoles

Ari Koskinen

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


A simple equation can be used for the evaluation of 13C chemical shifts of substituted imidazoles.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1637 - 1640
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DOI: 10.3987/R-1982-09-1637
Activated Nitriles in Heterocyclic Synthesis: A Novel Synthesis of 4-Hydroxy- and 4-Aminopyrano[2,3-c]pyrazoles

Bahia Y. Riad, Fathy A. Khalifa, Fathy M. Abdel Galil, and Mohamed H. Elnagdi

*Department of Chemistry, Faculty of Science, , University of Cairo, Giza, Egypt


A novel synthesis of pyrano[2,3-c]pyrazoles via the reaction of β-functional nitriles with 4-α-hydroxyethylene-and 4-α-aminoethylene-3-methyl-2-pyrazolin-5-one derivatives is reported.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1641 - 1645
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DOI: 10.3987/R-1982-09-1641
The Selectivity in N-Alkylation of Nicotine

Makoto Shibagaki, Hajime Matsushita, Saizo Shibata, Akira Saito, Yasuko Tsujino, and Hajime Kaneko

*Life Science Research Laboratory, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227-8512, Japan


In preference to pyrrolidine, pyridine moiety of nicotine was alkylated by alkyl halides. This preference seemed to result from the difference of steric hinderance around each nitrogen. The reactivity of pyridine moiety was accelerated by the electronic effect of pyrrolidine. The selective alkylation of pyridine appeared to be available for preparation of artificial antigen of nicotine.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1647 - 1654
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DOI: 10.3987/R-1982-09-1647
Metal Catalyzed Decomposition Diazoketones and Diazoamides of β-Lactams Part I: Penicillin Route to Carbapenems?

Ching-Pong Mak, Karl Baumann, Friedrich Mayerl, Christa Mayerl, and Hans Fliri

*Sandoz Research Institute, A-1235 Vieena, Austria


Metal catalyzed decomposition of diazoketones and diazoamides derived from penicillanic acid were investigated as approaches towards the synthesis of the carbapenem nucleus. Diazoketones derived from C-3 gave products of insertion into the C-5/S bond with inversion of stereochemistry. Homologous diazoketones yielded the tricyclic aminodiketone 10, derived from carbene insertion into the amide bond exclusively. Attaching the diazo group to the amino function led either to insertion into solvent or gave decomposition products.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1655 - 1661
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DOI: 10.3987/R-1982-09-1655
Anisofolin-A, a New Acylated Flavone Glucoside from Anisomeles ovata R. Br.

L. Jagan Mohan Rao, G. N. Krishna Kumari, and N. S. Prakasa Rao

*Department of Chemistry, Nagarjuna University, Nagarjunanagar 522 510, Andhra Pradesh, India


Aerial parts of Anisomeles ovata R.Br. contain a new acylated apigenin glucoside (0.002%). It was identified as apigenin-7-O-β-D-(3”, 6”-di-O-p-coumaroyl)-glucoside (anisofolin-A) by 13C nmr, 1H nmr and chemical degradative methods of anisofolin-A and its acetate.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1663 - 1665
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DOI: 10.3987/R-1982-09-1663
A One-step Synthesis of 2-Formylquinoxaline 1,4-Dioxides

Mustafa M. El-Abadelah, Ali A. Anani, and Zahida H. Khan

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


2-Formylquinoxaline 1,4-dioxide was easily prepared from the reaction of o-benzoquinone dioxime with cinnamaldehyde at low temperatures. A possible mechanism for the reaction is briefly discussed.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1667 - 1671
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DOI: 10.3987/R-1982-09-1667
Synthesis and Strereochemistry of (±)-Vincatine

Esahak Ali, Pulak K. Chakraborty, Ajit K. Chakravarty, and Satyesh C. Pakrashi

*Indian Institute of Chemical Biology, Calcutta-700 032, India


The structure and relative stereochemistry of vincatine, an alkaloid isolated from Vinca minor, have been established as 4B by synthesis of all the four possible stereoisomers of (±)-vincatine. 13C-Nmr spectra of the alkaloid and its synthetic intermediates are discussed.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1673 - 1675
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DOI: 10.3987/R-1982-09-1673
A New Synthesis of Ellipticine and Olivacine through Pyridine-3,4-quinodimethane Intermediates

Shinzo Kano, Eiichi Sugino, and Satoshi Hibino

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Thermolysis of 2-[3-methyl-α-(4-pyridyl)vinyl]indole (6a) at 500 °C for 3 min gave 11-demethylellipticine (7a). The similar reaction by using 2-[2,3-dimethyl-α-(4-pyridyl)vinyl]indole (6b) afforded olivacine (7b). Ellipticine and 11-demethylellipticine were obtained by thermolysis of 2-[3-ethyl-α-(4-pyridyl)vinyl]indole (6c).

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1677 - 1680
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DOI: 10.3987/R-1982-09-1677
The Synthesis of (—)-Isoretronecanol, (—)-Trachelanthamidine, and (—)-Supinidine from (S)-Proline

Heinrich Rüeger and Michael Benn

*Department of Chemistry, The University of Alberta, Calgary, Alberta, T2N, 1N4, Canada


Dieckmann cyclisation of (S)-N,2-di(carboethoxymethyl)pyrrolidine, made from (S)-proline, gave (8S)-1-carboethoxypyrrolizidin-2-one, which was then converted into (—)-isoretronecanol, (—)-trachelanthamidine, and (—)-supinidine.

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Report | Regular issue | Vol 19, No. 9, 1982, pp. 1681 - 1683
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DOI: 10.3987/R-1982-09-1681
Syntheses of Macrocycles from L-Amino Acid

Toyoshi Katagi and Hiromi Kuriyama

*School of Pharmaceutical Science , Mukogawa University, Edogwa-cho, Nishinomiya, Hyogo 663, Japan


Syntheses of 24-membered macrocycles were achieved by using L-phenylalanine and L-leucine as constituents.

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Review | Regular issue | Vol 19, No. 9, 1982, pp. 1685 - 1717
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DOI: 10.3987/R-1982-09-1685
Trichothecans — A Review

Chi Wi Ong

*University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, U.K.


The trichothecanes are a family of polyoxygenated sesquiterpenes showing a number of interesting pharmacological properties, i) antibiotic, ii) antifungal, iii) antiviral, iv) insecticidal and v) cytotoxic and cytostatic activity, the most common examples being trichodermin and verrucarol. Recent trichothecanes synthesis have been reviewed, including our contribution in the total synthesis of 12,13-Epoxy-14-methoxy-trichothecene using dienyl-Fe(CO)3 complexes.

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Review | Regular issue | Vol 19, No. 9, 1982, pp. 1719 - 1734
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DOI: 10.3987/R-1982-09-1719
Carbohydrates Containing Selenium

Zbigniew J. Witczak and Roy L. Whistler

*Department of Biochemistry, Purdue University, West Lafayette, Indiana 47907, U.S.A.


This review describes all the synthetically important methods which have been developed for the preparation of seleno-sugars.

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Review | Regular issue | Vol 19, No. 9, 1982, pp. 1735 - 1744
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DOI: 10.3987/R-1982-09-1735
Advances in Cyclopentenone Synthesis from Furans

Giovanni Piancatelli

*del C. N. R., c/o Istituto do Chimica Organica, Università degli Studi di Roma “La Sapienza”, Piazzale Aldo Moro 2 - 00185 Roma, Italy


Both 2-furylcarbinols and their 5-methyl derivatives are turned into the isomeric cyclopentenones through a molecular rearrangement catalyzed by acids or zinc chloride. The reaction was completely stereospecific and its mechanism was explained in terms of a thermal electrocyclic reaction of a 4π-electrons system; it showed a wide applicability and made easily available a large variety of cyclopentenones.
The oxidative ring fission of 2,5-dialkylfurans by pyridinium chlorochromate gave trans-ene dicarbonyl compounds; these were efficient buildlng blocks for the cyclopentenone synthesis and several applications are described.
2-(5-methyl-2-furyl)-1,3-dicarbonyl compounds, a new class of furan derivatives, afforded readily manipulable functionalized cyclopentenones, by a simple one-pot procedure, consisting first of the acid-catalyzed furan ring opening and, then, the intramolecular cyclization of the γ-diketone intermediates, directly to cyclopentenones in the same medium.

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28 data found. 1 - 28 listed