Regular Issue

Vol. 16, No. 8, 1981

18 data found. 1 - 18 listed
Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1271 - 1274
Published online:
DOI: 10.3987/R-1981-08-1271
Synthesis of Thieno[3,2-c]- and Thieno[2,3-c]pyrid-3-ones

Kyosuke Satake,* Toshiyuki Imai, Masaru Kimura, and Shiro Morosawa

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


The Friedel-Crafts cyclization of N-(3-thenyl)- and N-(2-thenyl)-glycine derivatives is described. The method leads to an alternative synthesis of 1,2,3,4-tetrahydro-N-[(2-chlorophenyl)methyl]thieno[3,2-c]pyridine(ticlopidine)(6d).

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1275 - 1279
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DOI: 10.3987/R-1981-08-1275
Alkaloids of Michelia fuscata Blume: The Structure and Synthesis of Magnolamine

Hitoshi Tanaka, Ayako Harada, Kazuhiko Ichino, and Kazuo Ito*

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan


The cleavage reaction of triethylmagnolamine (3) by sodium-liquid ammonia determined the location of phenolic functions in magnolamine (2). Furthermore, the synthesis of magnolamine was carried out by the Ullmann reaction of two optically active compounds (10) and (12). The synthetic product was completely identical with natural magnolamine by comparison of various spectra and t.l.c. behavior. Thus, it was clarified that the structure of magnolamine is indicated by the formula (2).

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1281 - 1285
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DOI: 10.3987/R-1981-08-1281
A Novel Synthesis of 2-Substituted Quinazolin-4(3H)-ones

Jan Svetlík*

*Drug Research Institute, Palárikova 31, 811 04 Bratislava, Slovakia


Aromatic or mixed carbodiimides and ketenimines react with ethyl allophanate to give corresponding substituted quinazolin-4(3H)-ones.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1287 - 1290
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DOI: 10.3987/R-1981-08-1287
High-pressure Diels-Alder Reactions of Furans with α-Chloro- and α-Acetoxyacrylonitrile

Hiyoshizo Kotsuki* and Hitoshi Nishizawa

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


The Diels-Alder reactions of furans with α-chloro- and α-acetoxyacrylonitrile very nicely proceeded under the conditions of 15 kbar and 30°C in dichloromethane. The adducts were proved to be a useful precursor for the synthesis of 7-oxa-bicyclo[2.2.1]heptanone derivatives.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1291 - 1294
Published online:
DOI: 10.3987/R-1981-08-1291
Chiral Route to Some Alkaloids through Asymmetric Iodolactonization

Seiichi Takano,* Chikara Murakata, Yoko Imamura, Nobuhiko Tamura, and Kunio Ogasawara

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


Three chiral γ-lactone derivatives (1), (2), and (3), leading to chiral synthesis of three alkaloids, (-)-secopandoline (4), (-)-quebrachamine (5), and (+)-mesembrine (6), have been synthesized through the asymmetric iodolactonization of the amides (8) from the symmetric carboxylic acids (7) and the chiral amines.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1295 - 1299
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DOI: 10.3987/R-1981-08-1295
Synthesis of 5-Aryl-5,6,7,8-tetrahydrothiazolo[3,4-a]pyridinium Bromides

Takeshi Hara* and John C. Sheehan

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, U.S.A.


5,6,7,8-Tetrahydro-5-phenylthiazolo[3,4-a]pyridinium bromide (1a) and 5-(p-chlorophenyl)-5,6,7,8-tetrahydrothiazolo[3,4-a]pyridinium bromide (1b) have been synthesized with 4-(3-carboethoxypropyl)-thiazole (3) and/or 4-(4-phenyl-3-butenyl)thiazole (9a) or 4-[4-(p-chlorophenyl)-3-butenyl]thiazole (9b) as an intermediate.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1301 - 1303
Published online:
DOI: 10.3987/R-1981-08-1301
Makomakine and Mokonine, New Indole Alkaloids from Aristoteria serrata

I. Ralph C. Bick* and Mohammad A. Hai

*Department of Chemistry, University of Tasmania, GPO Box 252C Hobart, Tasmania, 7001, Australia


A key intermediate, makomakine (I), involved in the proposed scheme of biosynthesis of the Aristotelia alkaloids, has been isolated from an A. serrata extract, together with makonine (II), a dehydroaristotelinone.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1305 - 1309
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DOI: 10.3987/R-1981-08-1305
A New Synthesis of Carbepenams through the Formation of the 1,5-Bond as a Final Step

Kapa Prasad,* Gerhard Schulz, Ching-Pong Mak, Helmut Hamberger, and Peter Stütz

*Sandoz Research Institute, A-1235 Vieena, Austria


Synthetic methods for the preparation of the racemic carbapenems 12 and 13 and an oxapenam 16 starting from diazoketone 11 are described.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1311 - 1314
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DOI: 10.3987/R-1981-08-1311
Structure of Forsythoside A, a Antibacterial Principle of Forsythia suspensa Leaves

Katsuya Endo, Kazuhiro Takahashi, Toyoko Abe, and Hiroshi Hikino*

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


A new glycoside, forsythoside A, exhibiting antibacterial activity, has been isolated from Frosythia suspensa leaves. Degradative and spectroscopic studies have established the structure of forsythoside A as shown in formula I.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1315 - 1319
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DOI: 10.3987/R-1981-08-1315
Synthesis of 2-Formyladenosine Using Diethoxyacetonitrile as a Synthon

Teiichi Murakami, Masami Otsuka, Susumu Kobayashi, and Masaji Ohno*

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan


Diethoxyacetonitrile has been utilized for the effective synthesis of adenine derivatives as a synthon. Novel 2-formyladenine (2b) and 2-formyladenosine (5b) have been prepared in high yields starting from AICN (1) and AICNR (4b), respectively.

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1321 - 1324
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DOI: 10.3987/R-1981-08-1321
Revised Structure of Isoterchebin, Isolated from Cornus officinalis

Takuo Okuda,* Tsutomu Hatano, and Tsutomu Yasui

*Faculty of Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


A dehydroellagitannin isolated from the fruit of Cornus officinalis, whose structure is assigned as 1,2,3-tri-O-galloyl-4,6-O-dehydrohexahydroxydiphenoyl-β-D-glucopyranose (I), is considered to be identical as isoterchebin which had been presumed to have structure (V).

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Communication | Regular issue | Vol 16, No. 8, 1981, pp. 1325 - 1328
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DOI: 10.3987/R-1981-08-1325
Dechlorination of Some Chloropyrazines and Their N-Oxides

Yasuo Akita and Akihiro Ohta*

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


By heating with sodium formate and tetrakis(triphenylphosphine)palladium, chloropyrazines were converted to the parent pyrazines in satisfactory yields. The chlorine atoms of chloropyrazine N-oxides could also be removed, leaving the N-O group.

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Report | Regular issue | Vol 16, No. 8, 1981, pp. 1329 - 1340
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DOI: 10.3987/R-1981-08-1329
Isolation and Characterization of a Substituted Benzpyridone from Darius Crude

Asha Masohan and Virendra Kumar Bhatia*

*Indian Institute of Petroleim, Dehradun, India


Heavy ends of petroleum are becoming important contributors to future petroleum requirements. A knowledge of the composition of these materials is, therefore, necessary for their efficient processing and use. Isolation and characterisation of a substituted benzpyridone from 300-470°C fraction of Darius crude is presented.

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Report | Regular issue | Vol 16, No. 8, 1981, pp. 1341 - 1344
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DOI: 10.3987/R-1981-08-1341
Novel and Convenient Syntheses of Substituted 1,4-Diazocines and 1,4-Diazonines

Geeta Singh and Kailash Nath Mehrotra*

*Chemistry Department, Faculty of Science, Banaras Hindu University, Varanasi-221 005, India


Treatment of dianils with sodium in dry ether followed by addition of 1,4-dichlorobutane and 1,5-dichloropentane gave 1,2,3,4-tetraaryl-1,4,5,6,7,8-hexahydro-1,4-diazocines and 1,2,3,4-tetraaryl-4,5,6,7,8,9-hexahydro-1H-1,4-diazonines respectively.

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Report | Regular issue | Vol 16, No. 8, 1981, pp. 1345 - 1351
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DOI: 10.3987/R-1981-08-1345
Bicyclic Peroxides from a 1,4-Diazepine

V. T. Ramakrishnan and Joseph H. Boyer*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.


An adduct, 3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo[4.2.1]non-3-ene, was obtained from 2,3-dicyano-5,7-dimethyl-6H-1,4-diazepine and hydrogen peroxide in the presence of alkali or a tertiary amine. It was dehydrogenated by iodobenzene diacetate into 3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo[4.2.1]nona-2,4-diene; further oxidation by m-chloroperbenzoic acid gave 4,5-dicyano-1,8-dimethyl-2,7-diaza-3,6,9,10-tetraoxatetracyclo[,405,7]undecane.

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Report | Regular issue | Vol 16, No. 8, 1981, pp. 1353 - 1355
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DOI: 10.3987/R-1981-08-1353
The Reaction of 3-Hydroxycoumarin with Benzalacetone

V. K. Ahluwalia,* Keya Mukherjee, and Nimmi Rani

*Department of Chemistry, University of Delhi, Delhi-110 007, India


The reaction of 3-hydroxycoumarin (I) with benzalacetone in presence of dioxane-piperidine afforded 3-hydroxy-4-(α-phenyl-β-acetylethyl )coumarin (IIa) which on acetylation with Ac2O/pyridine gave a cyclised product, 2-acetoxy-2-methyl-4-phenyl-10-oxo-3,4-dihydropyrano[2,3-c][1]benzopyran (III).

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Review | Regular issue | Vol 16, No. 8, 1981, pp. 1357 - 1365
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DOI: 10.3987/R-1981-08-1357
Synthesis of Ellipticine: Review and Computer Suggestions

R. Barone* and M. Chanon

*Laboratoire de Chimie Inorganique, Faculté des Sciences et Techniques de St.-Jérôme, Université e’Aix-Marseille III, Rue H. Poincaré, 13397 Marseille Cedex 13, France


A review of recent syntheses of ellipticine is presented and some suggestions of a computer assisted organic synthesis program are given.

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Review | Regular issue | Vol 16, No. 8, 1981, pp. 1367 - 1387
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DOI: 10.3987/R-1981-08-1367
The Synthesis and Reactions of Heterocycles under High Pressures

Kiyoshi Matsumoto,* Takane Uchida, and R. Morrin Acheson

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


In this review are brought together the representative results which are presently available concerning the use of high pressures on reactions involving heterocyclic compounds.

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18 data found. 1 - 18 listed