Regular Issue

Vol. 19, No. 10, 1982

30 data found. 1 - 30 listed
Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1793 - 1796
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DOI: 10.3987/R-1982-10-1793
Amoritin, Amorisin, and Amorilin: Three New Phenylated Flavanones from Amorpha fruticosa L.

Zsuzánna Rózsa, Judith Hohmann, Kálmán Szendrei, Johannes Reisch, and Iuliu Mester

*Department of Pharmacognosy, University Medical School, Szeged, Hungary


Three novel flavanones, amoritin, amorisin, and amorilin were isolated from the root bark of Amorpha fruticosa L. Their structures were determined on the basis of chemical and spectroscopic evidences.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1797 - 1800
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DOI: 10.3987/R-1982-10-1797
Synthesis of 7-Hydroxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-6-carboxylic Acids and 4-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acids

Régine Sola, Daniel Frehel, Jean-Pierre Maffrand, and Jean Brugidou

*Sanofi Recherche, Linge Hèmobiologie, 195, route d’Espagne, 31024 Toulouse, France


This paper deals with the synthesis of 7-hydroxy-4,5,6,7-tetrahydrothieno[3,2-c] pyridine-6- and 4-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids by Pictet-Spengler cyclisation of the corresponding β-thienylserines and β-phenylserines respectively. Their diastereoisomers were separated and identified.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1801 - 1805
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DOI: 10.3987/R-1982-10-1801
Neopulchellin Conformation

Seiichi Inayama, Kenzo Harimaya, Hitoshi Hori, Takeshi Kawamata, Tamiko Ohkura, Hikaru Nakamura, and Yoichi Iitaka

*Pharmaceutical Institute, Pharmaceutical Institute, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan


Neopulchellin (1) was found to show that the cycloheptane ring fused to the cis butyrolactone adopts a boat conformation both in solid and in solution, in contrast with the half-chair form in the trans-lactone isomer, pulchellin (3), on the basis of X-ray diffraction of 1 and comparison of 400 MHz 1H-nmr and cd spectra of 1 and 3.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1807 - 1812
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DOI: 10.3987/R-1982-10-1807
Acid-catalysed Red-Ox Rearrangement of a Hemiketal

Jean Le Men, Monique Zèches, and Françoise Sigaut

*Laboratoire d’Isolement, Transformation et Synthese de Substances Naturelles, UFR de Pharmacie, associe au CNRS, Université de Champagne-Ardenne, 51 rue Cognacq-Jay-F 51096 Reims Cedex, France


Hemiketals 5a,b generated from the indole alkaloids ajmalicine 1a and tetraphylline 1b, yielded the isomeric hemiketals 7a,b upan acidic treatment. Ajmalicine 1a was converted in Low yield to dihydrocorynantheol 10a through 7a.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1813 - 1818
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DOI: 10.3987/R-1982-10-1813
New Tricyclic Ketones Derived from Eudesmanolide

Seiichi Inayama, Hitoshi Hori, Nobuko Shimizu, Ashok Kumar Singh, Takeshi Kawamata, Tetsuichi Shibata, and Yoichi Iitaka

*Pharmaceutical Institute, School of Medicine, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan


The complete structures of new tricyclic keto olefins (4a,b) formed by cyclization-skeletal rearrangement of an eudesmanolide (1) with phosphoryl chloride were established by spectroscopic and X-ray crystallographic analyses of an unusual diol (6a), epoxy ketones (7a,b) and α,β-unsaturated ketones (8a,b).

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1819 - 1822
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DOI: 10.3987/R-1982-10-1819
A New Synthesis of 4-Chromanones

Jaime Primo, Rosa Torma, and Miguel A. Miranda

*Department of Toxicology, University of Cagliari, Via Ospedale 72, I-09124 Cagliari, Italy


Aryl esters of α,β-unsaturated carboxylic acids undergo photorearrangement, followed by basic cyclization, to give 4-chromanones. Reduction/dehydration of these compounds affords 2H-chromenes in excellent overall yields.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1823 - 1828
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DOI: 10.3987/R-1982-10-1823
Synthesis of Some Oxazolin-5-one-4-spiro-1’-cyclopropanes Having Functional Groups and Their Thermal Rearrangements

Otohiko Tsuge, Michihiko Noguchi, and Hiroyuki Moriyama

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


4-Cycloalkylidene-2-phenyl-2-oxazolin-5-ones reacted with carbonyl-stabilized sulfur methylides to give the corresponding dispiro compounds, which on heating were converted into retro-ene reaction products. The reaction of 4-cinnamylidene-2-phenyl-2-oxazolin-5-one with sulfur allylides afforded the Cope rearrangement products, accompanied by a spiro-cis-divinylcyclopropane in a certain case.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1829 - 1833
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DOI: 10.3987/R-1982-10-1829
Double Annelation of the Enamine-Imines, Isoquinoline and β-Carboline Derivatives, with 6-Methylpyran-2-one-3,5-dicarboxylates

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

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


6-Methylpyran-2-one-3,5-dicarboxylates (11a and 11b) were synthesized by the reaction of dimethyl methoxymethylenemalonate (9) and acetoacetates in the presence of sodium hydride followed by the acidic treatment. Reaction of the enamine-imines (1, 12 and 16) with the pyran-2-ones (11a and 11b) produced the tetra-(15a and 15b) and pentacyclic compounds (17a and 17b) by the double annelation. The epoxyetheno-bridge was reductively cleaved at pH 3 giving the benzo-(18) and indoloquinolizidines (19).

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1835 - 1838
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DOI: 10.3987/R-1982-10-1835
An Alternative Biomimetic Synthesis of (±)-Campothecin

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

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


14-tert-Butoxycarbonyl-12b,2-epoxyetheno-1,12b,2,3- 6,7-hexahydro-3-methoxycarbonyl-13-methylindolo[2,3-a]quinolizin-4-one (2) synthesized by the enamine-imine double annelation method was converted to the acetate (12) which had been correlated with (±)-camptothecin (1a) in two steps. The epoxyetheno-bridge was cleaved by the reaction with a mixture of ethanedithiol and trifluoroacetic acid.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1839 - 1843
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DOI: 10.3987/R-1982-10-1839
Furan to Pyrone Conversions

Franz Josef Jäggi, Masayoshi Tsubuki, Thomas Y. R. Tsai, and Karel Wiesner

*Natural Products Research Center, Department of Chemistry, University of New Brunswick, Bag Service #45222, Fredericton, New Brunswick, E3b 5A3, Canada


Conversions of the furyl derivatives 2, 3 and 6 to the α-pyrones 10 and 16 have been studied. These techniques are applicable in conjunction with our “cardenolide furan methodology” to the synthesis of bufalin III and γ-isobufalin IV, as well as to a variety of other synthetic problems.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1845 - 1848
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DOI: 10.3987/R-1982-10-1845
Ring Transformation Reactions of Novel Xanthinium Ylides

Mikio Hori, Tadashi Kataoka, Hiroshi Shimizu, Eiji Imai, Yukiharu Matsumoto, and Masanori Kawachi

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


The novel xanthinium ylides were generated and reacted with acetylenic compounds to give the ring transformed products, 5-pyrrolouracil derivatives and/or pyrrolo[l,2-f]pteridine derivatives. The mechanism of these reactions was also discussed.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1849 - 1852
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DOI: 10.3987/R-1982-10-1849
Substitutent Effects on the Carbon-13 Chemical Shifts of Ylidic Carbons in Pyridinium Dicyanomethylides

Kiyoshi Matsumoto, Takane Uchida, and Chizuko Uno

*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan


A correlation between the carbon-13 chemical shifts of carbanions in 4-substituted pyridinium dicyanomethylides has been described. At present, best correlation coefficient (0.969) was obtained using the Inamoto-Masuda methods, i.e. ι and μ parameters.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1853 - 1854
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DOI: 10.3987/R-1982-10-1853
Nitrogen Nucleophile Displacements of the Acetate Group from 4-Acetoxyazatidin-2-one

Malcolm M. Cambell and Bernard P. Connarty

*School of Chemistry, University of Bath, Bath, Avon. BA2 7AY, U.K.


N-Tosylamino nucleophiles displaced acetate from 4-acetoxyazetidin- 2-one,complementing other studies of heteronucleophiles. Annelation procedures for model 4,6-bicyclic β-lactams were established.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1855 - 1860
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DOI: 10.3987/R-1982-10-1855
Mulberrofuran D, a New Isoprenoid 2-Arylbenzofuran from the Root Barks of the Mulberry Tree (Morus australis Poir.)

Taro Nomura, Toshio Fukai, Takako Shimada, and Ih-Sheng Chen

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


From the benzene extract of the root barks of the mulberry tree (Morus australis Poir.), a novel isoprene-substituted 2-arylbenzofuran derivative, mulberrofuran D, was isolated whose structure was shown to be I on the basis of spectral and chemical data.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1861 - 1863
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DOI: 10.3987/R-1982-10-1861
A Formation of Carbacepham Ring System by 1,6-Bond Coupling through a Radical Cyclization Reaction

Tetsuji Kametani and Toshio Honda

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


A facile formation of carbacepham ring system was achieved by 1,6-bond formation of 3, employing a radical cyclization as a key reaction.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1865 - 1868
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DOI: 10.3987/R-1982-10-1865
Studies on as-Triazine Derivatives. II. A Ring-cleavage Reaction of 3-Trichloromethyl-5,6-diphenyl-1,2,4-triazine and Related Compounds

Shoetsu Konno, Masaaki Yokoyama, and Hiroshi Yamanaka

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


3-Chloromethyl- (4), 3-dichloromethyl- (3), and 3- trichloromethyl-5,6-diphenyl-1,2,4-triazine (2) were synthesized from 3-methyl-5,6-diphenyl-1,2,4-triazine (1). The reaction of 4 with sodium ethoxide in ethanol simply afforded the corresponding 3-ethoxymethyl compound. In contrast to this reaction, when 2 and 3 were treated with sodium alkoxide, an unexpected ring-cleavage reaction occurred instead of simple nucleophilic attack to chloromethyl groups. The structure of the products and the reaction mechanism are discussed.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1869 - 1872
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DOI: 10.3987/R-1982-10-1869
Studies on as-Triazine Derivatives. III. Preparation of 3-Alkenyl-1,2,4-triazine Derivatives by Means of Witting Reaction

Shoestu Konno, Estuko Takaharu, Yuichi Aizawa, and Hiroshi Yamanaka

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


The reaction of 3-trichloromethyl-5,6-diphenyl-1,2,4-triazine with triphenylphosphine proceeded reductively, and α-[3- (5,6-diphenyl-1,2,4-triazinyl)]methylenetriphenylphosphorane was obtained as stable, yellow prisms. The phosphorane smoothly reacted with various aldehydes in boiling benzene to give the corresponding 3-alkenyl compounds, whereas the reaction with ketones failed to give any significant products under the same conditions.

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Communication | Regular issue | Vol 19, No. 10, 1982, pp. 1873 - 1877
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DOI: 10.3987/R-1982-10-1873
A Route for Total Synthesis of Ergot Alkaloids. Synthesis of the Despyrrole Analogs of Methyl Lysergate, Isolysergol, and Isofumigaclavine A.

Toshio Kiguchi, Chiyomi Hashimoto, Takeaki Naito, and Ichiya Ninomiya

*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, kobe, Hyogo 658, Japan


A general and potential synthetic route involving reductive photocyclization of enamide followed by the formation of glycols and their cleavage for total synthesis of ergot alkaloids was developed using the model compounds (3,6,7, and 13).

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1879 - 1882
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DOI: 10.3987/R-1982-10-1879
The Reaction of 2,4-Dichloroquinazoline with N-Alkylpyrrolidines

Hideki Miki and Fumiko Kasahara

*Central Research Division, Takeda Chemical Industries, Ltd., 17-85 Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan


The reaction of 2,4-dichloroquinazoline with N-methylpyrrolidine gave N-(2-chloro-4-quinazolinyl)-N-methylpyrrolidinium chloride, which was heated to give 2-chloro-4-(N-methyl-4-chloro- butylamino)quinazoline and reacted also with water in the presence of excess N-methylpyrrolidine to give a stable zwitter ion, 4-(N- methylpyrrolidino)-2-quinazolinolate.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1883 - 1888
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DOI: 10.3987/R-1982-10-1883
The Absolute Configuration of Stephanine and Crebanine

Jun-ichi Kunitomo, Miyoko Satoh, Yasuo Watanabe, Matao Matsui, Masatoshi Inoue, and Toshimasa Ishida

*Faculty of Pharmaceutical Science, Mukogawa-Women’s University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan


The crystal structure of natural stephanine (1) has been determined by X-ray diffraction. The C-6a position was confirmed to be of the R-configuration. O-Methyl derivatives of the products by cleavage reaction with sodium in liquid ammonia of stephanine (1) and crebanine (2) were both identified as 2,8-dimethoxyaporphine (3). This showed that crebanine (2) was of the R-configuration which has also been reported based on CD data. This work yielded the exact configuration at C-6a far all known aporphine-type alkaloids.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1889 - 1894
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DOI: 10.3987/R-1982-10-1889
Oxides of Heterocyclic Quinones. N-Oxides and Epoxides of Quinoline- and Isoquinoline-5,8-dione

Jacek Mlochowski, Krystian Kloc, and Joanna Piatkowska

*Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology, Wyb. Wyspianskigo 27, 50-375 Wroclaw, Poland


The syntheses of 6,7-epoxides and N-oxides of quinoline- and isoquinoline-5,8-diones and of their 6,7-dichloro derivatives are described. The key step of synthesis is oxidation of quinoline or isoquinoline N-oxides bearing the hydroxy or amino groups in the position 5 and 8.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1895 - 1901
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DOI: 10.3987/R-1982-10-1895
Synthesis of Benzo[5,6]cyclohept[1,2,3ij]isoquinolines as Rigid Congeners of Tetrahydropapaveroline

Padam N. Sharma, Kenner C. Rice, and Arnold Brossi

*Medical Chemistry Section, Laboratory of Chemistry, NIDDK, National Institute of Health, Bethesda, MD 20892, U.S.A.


The synthesis of several 5,6,9,10-tetraoxygenated 1,2,3,7 ,12,12a-hexahydrobenzo[5,6]cyclohept[l,2,3-ij]isoquinolines from (±)-coreximine (3) and its diacetate 4 is described. The secondary amine 8 afforded upon N-methylation the isoquinoline 7, previously obtained by Kametani et al through a different route. Aromatization of 8 afforded the aromatic isoquinoline 10 and O-demethylation of 8 with refluxing 48% HBr gave 9, a tetracyclic analog of tetrahydropapaveroline (THP).

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1903 - 1908
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DOI: 10.3987/R-1982-10-1903
vic-Iodothiocyanates and Iodoisothiocyanates. Part 7. The Synthesis of 2-Benzylamino-2-thiazolines

Richard C. Cambie, Peter S. Rutledge, Gary A. Strange, and Paul D. Woodgate

*Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand


Treatment of vic-iodoisothiocyanates with benzylamine gives 2-benzylamino-2-thiazolines. Inseparable mixtures of isomeric vic-iodoisothiocyanates are readily separated as these derivatives.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1909 - 1913
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DOI: 10.3987/R-1982-10-1909
Heterocage Compound [II]. Synthesis of Thiacane Tricyclic Systems: Thiabrendane and Thiaisotwistane Skeleton with an Amino Function and Their S-Oxide Derivatives

Shun Inokuma, Akihiko Sugie, Koichi Moriguchi, Hiromi Shimomura, and Junki Katsube

*Sumitomo Pharmaceuticals Research Center, 1-98, Kasugadenaka 3-chome, Konohana-ku, Osaka 554-0022, Japan


A series of thiacage tricyclic systems with amino functions were synthesized in order to examine their chemical, physicochemical and biological properties. Their S-oxide derivatives were also synthesized.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1915 - 1920
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DOI: 10.3987/R-1982-10-1915
High-pressure Reactions of Pyrroles with Dimethyl Acetylenedicarboxylate

Hiyoshizo Kotsuki, Yuichiro Mori, Hitoshi Nishizawa, Masamitsu Ochi, and Kiyoshi Matsuoka

*Department of Material Science, Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan


The cycloaddition reactions of pyrroles with dimethyl acetylenedicarboxylate were performed under the conditions of 15 kbar and 40 °C in dichloromethane.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1921 - 1924
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DOI: 10.3987/R-1982-10-1921
Formation of 1,2,3,5-Tetrasubstituted 2-Pyrrolin-4-ones and 1,2,3-Trisubstituted Pyrroles from Diphenylcyclopropenone and 1,4-Diazabutadienes

Masahiko Takahashi, Tomomi Funaki, Hisao Honda, Yoshiyuki Yokoyama, and Hideo Takimoto

*Department of Materials Sciences, Faculty of Engineering, Ibaraki University, 4-12-1 Nakanarusawamachi, Hitachi, Ibaraki 316-8511, Japan


The reaction of diphenylcyclopropenone (1) with 1,4-diaryl-1,4-diazabutadienes (2) afforded 1-aryl-5-(N-aryl) iminomethyl-2,3-diphenyl-2-pyrrolin-4-ones (3) as major products and 1-aryl-2,3-diphenylpyrroles (11) as minor products.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1925 - 1929
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DOI: 10.3987/R-1982-10-1925
Reactions with Activated Nitriles: Some New Approaches for the Synthesis of Pyridine Derivatives

Hamed A. Daboun, Sadek E. Abdou, and Mahmoud M. Khader

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


The reaction of 2-amino-1,1,3-tricyanopropene (1) with acetylacetone and with salicylaldehyde gave the pyridine derivatives 2 and 9, respectively. Compounds 2 and 9 were transformed into pyridine derivatives 4 and pyrazolo[4,3-c]pyridine derivative 10 on treatment with hydrazines. 9 reacted with malononitrile and benzoylacetonitrile to give the pyrido[3,2-c]pyridine derivatives 11 and 12, respectively. The structures of the isolated products were established by the results of elemental analyses and IR and 1H NMR spectral data.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1931 - 1934
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DOI: 10.3987/R-1982-10-1931
(—)-4α-Hydroxysparteine, a New Natural Product from Acosmium panamense

Manuel F. Balandrin and A. Douglas Kinghorn

*Department of Pharmacognosy and Pharmacology, College of Pharmacy, University of Illinois at the Medical Center, Chicago, IL 60612, U.S.A.


(-)-1-4α-Hydroxysparteine (1) was obtained for the first time as a natural product from a methanol extract of the bark of Acosmium panamense (Leguminosae). The structure and stereochemistry of 1 were confirmed by gc/ms comparison of the acetylated product of 1 with authentic samples of 4α-acetoxysparteine (2) and 4β-acetoxysparteine (6). 4α-Hydroxysparteine , (1) and 2,4-d2-4α-hydroxysparteine (7) were prepared by reduction of multi-florine (3) with sodium borohydride and sodium borodeuteride in methanol, respectively.

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Report | Regular issue | Vol 19, No. 10, 1982, pp. 1935 - 1938
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DOI: 10.3987/R-1982-10-1935
Reaction of Banzo[b]thiopine 1,1-Dioxide with Iodine Azide and Bromide Azide: X-Ray Structure Analysis of the Adducts

Yasumitsu Tamura, Masayoshi Tsunekawa, Said M. M. Bayomi, Sund Kwon, Masazumi Ikeda, and Masaru Kido

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


Benzo[b]thiophene 1,1-dioxide reacts with iodine azide and bromine azide to give trans-3-azido-2-iodo- and trans-2-azido-3-bromo-2,3-dihydrobenzo[b]thiophene 1,1-dioxides, respectively, whose structures were determined by X-ray structure analyses.

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Review | Regular issue | Vol 19, No. 10, 1982, pp. 1939 - 1966
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DOI: 10.3987/R-1982-10-1939
Some Consequences of Lone Pair Interactions in the Chemistry of Monosaccharides

Vernon G. S. Box

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


The lone pair repulsions implicated in the anomeric effect are suggested to increase the nucleophilicities of the participating atoms (β-effect). An analogous longer-range effect (the γ-effect) is also proposed, and the roles of these effects demonstrated in mechanistic proposals for the oxidation of acetals and some reductions of the glycosuloses.

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30 data found. 1 - 30 listed