Special Issue

Tetsuji Kametani's Special Issues, Vol. 15, No. 2, 1981

118 data found. 91 - 118 listedFirst Previous
Communication | Special issue | Vol 15, No. 2, 1981, pp. 1179 - 1185
Published online:
DOI: 10.3987/S-1981-02-1179
Heterocycles from 2-Alkyl- or Arylthio-1-chloroenamines

Léon Ghosez,* Patrick Notté, Christiane Bernard-Henriet, and Robert Maurin

*Laboratoire de Chimie Organique de Synthése, Université de Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium


2-alkyl-or arylthio-1-chloroenamines are readily prepared from tertiary amides or from ynamines. The 2-arylthio derivatives are readily cyclized to 3-dialkylaminobenzothiophenes in the presence of Lewis acids. With sodium azide they give 2-amino-1-azirines bearing a thioether group at position 3. These highly functionalized azirines are potential precursors of the 2-amino-1-azirinyl-cations.

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Communication | Special issue | Vol 15, No. 2, 1981, pp. 1187 - 1193
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DOI: 10.3987/S-1981-02-1187
Propellanes. LVII. Reaction of an Optically Active Tetraenic Propellane Imide with an Optically Active Substituted Triazolinedione

Michael Peled and David Ginsburg*

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


Optically active components were reacted in a Diels-Alder reaction in order to obtain additional infomation with respect to secondary orbital interactions in such systems. Separation of diastereomeric adducts failed when racemic imide was employed.

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Communication | Special issue | Vol 15, No. 2, 1981, pp. 1195 - 1198
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DOI: 10.3987/S-1981-02-1195
Ultraviolet Absorption Spectra of 4-Amino-and 4-Dimethylaminopyridines: Effects of Concentration and Solvent

Chikara Kaneko,* Kazuhiro Shiba, and Harue Fujii

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


The effect of concentration on the UV spectra of 4-aminopyridine and its derivatives in various solvents was studied in the concentration range from 10-6 to 10-3 M/l. At high concentration, 4-aminopyridines were found to form molecular aggregates (loosely bonded dimers) showing the maxima around 245-260 nm, whose position corresponded to those previously assigned as the 1La-band of the monomer. The monomeric form of these pyridines showed a single absorption maximum around 265-280 nm, which had been previously assigned as the 1Lb-band of the monomer.

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Communication | Special issue | Vol 15, No. 2, 1981, pp. 1199 - 1204
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DOI: 10.3987/S-1981-02-1199
Synthesis of Uroporphyrin-III, and Related Hepta- and Penta-carboxylic Porphyrins by Modifications of the MacDonald Method

M. Charkrabarty, S. A. Ali, G. Philip, and A. H. Jackson*

*Department of Chemistry, University College, Cardiff, Wales, U.K.


A modification of the McDonald route has been developed in which all four pyrrole units of uroporphyrin-III have been derived from the same conveniently prepared starting pyrrole. Related hepta- and penta- carboxylic porphyrins have also been synthesised by condensation of appropriate α-fomyl pyrromethae-α’-carboxylic acids; in each case other porphyrins with different numbers of acidic side-chains were also produced but the desired products were easily separated (as their methyl esters) by h.p.l.c.

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Communication | Special issue | Vol 15, No. 2, 1981, pp. 1205 - 1207
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DOI: 10.3987/S-1981-02-1205
The Conversion of L-Glutamate to L-Tyrosine

Samuel Danishefsky,* Joel Morris, and Lane A. Clizbe

*Department of Chemistry, University of Pittsburgh, Pittsburgh,15260, Pakistan


The Diels Alder reaction of a glutamate derived dienophile with trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene affords a spirodienone. This, upon treatment with aqueous base leads to N-CBz-tyrosine. Optical activity is substantially maintained throughout the process.

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Report | Special issue | Vol 15, No. 2, 1981, pp. 1209 - 1212
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DOI: 10.3987/S-1981-02-1209
The Synthesis of Regiospecifically 13C-Labeled α-Tocopheryl Acetate

M. Kajiwara,* O. Sakamoto, H. Katsura, and S. Ohta

*Shiseido Laboratories, 1050 Nippa-cho, Kohoku-ku, Yokohama 223, Japan


A convenient procedure for the synthesis of regiospecifically 13C-labeled α-tocopheryl acetate of high enrichment is described.

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Report | Special issue | Vol 15, No. 2, 1981, pp. 1213 - 1218
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DOI: 10.3987/S-1981-02-1213
Benzo- and Indoloquinolizine Derivatives XX. Synthesis and Conformation of 5,6,8,9-Tetrahydro-13b-H -dibenzo[a,h]quinolizine and 5,6,8,9,14,14b-Hexahydrobenzo[a]indolo[3,2-h ]quinolizine

F. Vlaeminck, E. De Cock, D. Tourwé, and G.Van Binst*

*Laboratoium voor organische Chemie, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussel, Belgium


Dibenzo[a,h]quinolizidines are prepared by an imminium cyclization or by PPA cyclization of the ethyleneoxide adduct of 1,2,3,4-tetrahydro-1-phenylisoquinoline. The conformational equilibrium in the title compounds is studied by 13C NMR.

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Report | Special issue | Vol 15, No. 2, 1981, pp. 1219 - 1221
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DOI: 10.3987/S-1981-02-1219
Anodic Oxidation of the Bridged Ether Derivative of (±)-Reticuline

Masayuki Murase and Seisho Tobinaga*

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


Anodic oxidation of the bridged ether derivative (7) of (±)-reticuline (1b), synthesized from the N-carbethoxy-1-benzyl-tetrahydroisoquinoline (1a), afforded the proerythrinadienone type coupling product (8) and the morphinadienone type coupling product (9).

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Report | Special issue | Vol 15, No. 2, 1981, pp. 1223 - 1225
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DOI: 10.3987/S-1981-02-1223
1,3-Dipolar Cycloaddition Reaction of Trifluoroacetonitrile with Heterocyclic Ylides

Yoshiro Kobayashi,* Itsumaro Kumadaki, and Emi Kobayashi

*Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Trifluoroacetonitrile is found to be a good dipolarophile and reacts with heterocyclic N-ylides to give (trifluoromethyl)imidazolopyridine compounds.

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Report | Special issue | Vol 15, No. 2, 1981, pp. 1227 - 1232
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DOI: 10.3987/S-1981-02-1227
New Heterocycles-Acces to Thieno[3,2-b][f ]- and Thieno[2,3-b][f ]benzazepine Derivatives

Jacques Guillaume, Lucien Nédélec,* Michel Cariou, and André Allais

*Centre de Recherche ROUSSEL-UCLAF, 102-111, route de Noisy, 93230 Romainville, France


The synthesis of the new heterocycles in the title is described. From these, the thieno analogues of imipramine and clomipramine were prepared.

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Report | Special issue | Vol 15, No. 2, 1981, pp. 1233 - 1237
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DOI: 10.3987/S-1981-02-1233
Studies on the Structure-Activity Relationship of Thiepin and Oxepin Derivatives to Anti-inflammatory Activities

Yoshio Suzuki,* Tohru Yamanaka, Yoshihiro Tanaka, Kiyosato Niu, Masakastu Mizushima, Sigeo Ikeda, Yasuo Fujimoto, and Shigeru Yamabe

*Research Institute, Nippoon Chemiphar Co., Ltd., Hikokawato 1-22-1, Misato-shi, Saitama 341-0005, Japan


A series of dibenzo[b,f]thiepincarboxylic acid derivatives has been synthesized and it’s anti-inflammatory activity was examined by the method of carrageenan edema.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1239 - 1256
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DOI: 10.3987/S-1981-02-1239
Hypotensive Principles from Plants

Shinji Funayama and Hiroshi Hikino*

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan


This review article summarizes our knowledge regarding the structure, occurence and activity of known substances showing hypotensive activity in the plant kingdom.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1257 - 1274
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DOI: 10.3987/S-1981-02-1257
Indole Alkaloid Biosynthesis

A. Ian Scott,* Siu-Leung Lee, Michael G. Culver, Winnie Wan, Toshifumi Hirata, Francoise Guéritte, Rober L. Baxter, Hans Nordlöv, Craig A. Dorschel, Hajime Mizukami, and Neil E. Mackenzie

*Department of Chemistry, Texas A & M University, College Station, Texas 77843-3255, U.S.A.


The early and late stages of indole alkaloid biosynthesis in Catharanthus roseus were studied by cell-free enzymes isolated from the plant and its tissue culture. The intermediacy of strictosidine (isovincoside), geissoschizine and other compounds in the formation of ajmalicine is discussed. Vinblastine, the antineoplastic dimeric alkaloid, was synthesized enzymically from a semi-synthetic precursor, anhydrovinblastine.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1275 - 1283
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DOI: 10.3987/S-1981-02-1275
The N-O-O Triangulation Hypothesis-An Assessment After One Decade

C. C. Cheng* and Robert K. Y. Zee-Cheng

*Drug Development Laboratory, The University of Kansas Cancer Center and Department of Pharmacology, Toxicology & Therapeutics, The University of Kansas Medical Center, Kansas City, Kansas 66160-7419, U.S.A.


A triangular atomic arrangement composed of three electronegative atoms (one nitrogen and two oxygen) was observed among many antineoplastic compounds in 1970. Today, the extent of the application of this hypothesis is assessed with affirmative and nonconfirmative examples provided from the literature. The hypothesis has been used for the design and synthesis of several interesting antineoplastic agents, including DHAQ.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1285 - 1308
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DOI: 10.3987/S-1981-02-1285
A Correlation of the Chemistries of Two Thienopyridines with Those of Benzo[b]thiophene and Quinoline

L. H. Klemm*

*Department of Chemistry, University of Oregon, Eugene, OR 97403, U.S.A.


All of the presently known chemistries (including SE and SN reactions, heteroatomic oxidations, reactions of ring substituents, and reactions of N- and S-oxides) of the thieno[2,3-b]pyridine and thieno[3,2-b]pyridine (TP) systems are shown to be interpretable as amalgamations of the chemistries of the reference compounds benzo[b]thiophene (BT) and quinoline (Q). Three general relationships are noted, viz. (a) cases where all systems (TP, BT, and Q) give reactions which are consistent with one another, (b) cases where the TP system gives reaction analogous to that of the BT or Q system only, and (c) cases where the TP system gives dual reactions as if it were a mixture of the BT and Q systems. In particular, isosteric relationships are commonly observed. Electronic interactions between the rings in TP are considered.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1309 - 1321
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DOI: 10.3987/S-1981-02-1309
Recent Chemistry of Some Indian Piper Species

Balawant S. Joshi*

*CIBA-GEIGY Research Centre, Goregaon Bombay 400063, India


This review summarises some of our work on the chemistry of six Indian Piper species.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1323 - 1348
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DOI: 10.3987/S-1981-02-1323
Tannis of Medicinal Plants and Drugs

Takuo Okuda,* Takashi Yoshida, Kazuo Mori, and Tsutomu Hatano

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


This review summarizes the research carried out in recent years at the author’s laboratory on tannins in several medicinal plants and drugs, most of which have been presumed to contain tannin as the main active principle.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1349 - 1394
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DOI: 10.3987/S-1981-02-1349
The Novel Dihydrothiazolo[3,2-a]pyridinium-8-olate and Closely Related Systems: Syntheses and Reactions

Kjell Undheim*

*Department of Chemistry, University of Oslo, P.O.Box 1033, Blindern, N-0315 Oslo, Norway


This review covers the chemistry of the dihydrothiazolo[3,2-a]pyridinium-8-olate system, of its quinoline homologues, of amino- and nitro-dihydrothiazolo[3,2-a]pyridinium derivatives, of the dihydrothiazolo[3,2-c]pyrimidinium-8-olate system, and of the thiazolo[3,2-a]pyridinium-8- and -3-olate systems as developed in the author’s laboratories. The dihydrothiazoles are formed by cyclisations over thio-azines. Asymmetric induction has been achieved in Michael adducts with thiolactams. Stereochemistry and mechanisms in adduct and cyclisation reactions have been elucidated; anchimeric involvement of the sulfur has been demonstrated. Optically active 3-carboxydihydrothiazoles are available from (R)-cysteine and oxidized furfurals; other α-pyridino acids are similarly prepared. Syntheses of thiazoles are described. Electrophilic substitution occurs readily in azinium-olates. Regiospecific deuteriations are described. N-Vinylpyridine-2-thiones are conveniently prepared from dihydrothiazoles. Photolysis of pyridinium-olates yielded the valence isomeric aziridines which are rearranged to α-pyridinones. Anchimeric assistance in oxidation of 3-carboxydihydrothiazoles yielded mainly the 1,3-cis oxide; ready decarboxylation of optically active reactant yielded the sulfoxide enantiomer. The N-chloroacetyl protecting group in peptides is removed by reaction with 3-nitropyridine-2-thione and cyclisation in cold TFA to the thiazolo[3,2-a]pyridinium-3-olate. Relevant X-ray data from structure analyses, pKa values, NMR data, and ionisation potentials in structure analyses in the gas phase, are discussed.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1395 - 1404
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DOI: 10.3987/S-1981-02-1395
Relative Reactivity of the Aromatic Ring in Benzo-1,3-dioxole, Its Cyclohomologues and Veratrole

V. K. Dauksas,* G. V. Purvaneckas, E. B. Udrenaite, V. L. Gineityte, and A. V. Barauskaite

*Kapsukas State University, U.S.S.R.


A study of the reactivities of benzo-1,3dioxole (1, n=1), benzo-1,4-dioxane (1, n=2), benzo-1,5-dioxepane (1, n=3) and veratrole (2) is of great interest, since those 1,2-dialkoxybenzenes are essential structural fragments of many natural and synthetic biologically active substances1,2 and the synthesis of their derivatives often results in the formation of new compounds of practical interest.2 However, many aspects of reactivity and other properties of compounds 1 and 2 have received insufficient study and the standpoints referred to in publications are of contradictory nature and need additional experimental verification.2-13

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1405 - 1431
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DOI: 10.3987/S-1981-02-1405
Studies on Plant Tissue Cultures

James P. Kutney*

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada


A summary of recent experiments with various plant tissue cultures at the University of British Columbia and at the Prairie Regional Laboratory, National Research Council of Canada, Saskatoon, is provided. The main emphasis of the research program is to propagate tissue cultures from plant species known to produce active agents of interest in the cancer area.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1433 - 1462
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DOI: 10.3987/S-1981-02-1433
Enamide Photocyclization and Its Application to the Synthesis of Heterocycles

Ichiya Ninomiya* and Takeaki Naito

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


Enamides are class of the conjugated systems which contain two C=C double bonds, irrespective of their olefinic or aromatic nature, on both sides of an amide group, thus forming six π-electron conjugated systems capable of undergoing smooth cyclization under irradiation. The application of enamide photocyclization to the synthesis of a variety of six-membered lactams as exemplified by a number of alkaloid and heterocycle syntheses proved this reaction as of a useful general synthetic tool for the construction of various heterocyclic compounds.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1463 - 1488
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DOI: 10.3987/S-1981-02-1463
Studies in Protoberberine Aikaloids XVII — Neooxyberberine Acetone

Tuticorin R. Govindachari,* Bantwal R. Pai, Sundaramurthy Rajeswari, Sankaran Natarajan, Sundaram Chandrasekaran, Manakkal S. Premila, and Ramamurthy Charubala Kailasam venkatesan and Mohan madhav Bhadbhade Kuppuswamy Nagrajan W.J. richter

*Department of Chemistry, Presidency College, Madras 600005, India


Structure and Stereochemistry of Neooxyberberine acetone, 8,13a-(2’-Oxopropano)-13-hydroxy-2,3-methylenedioxy-9,10-dimethoxydibenzo-(a,g)-quinolizine 4. Chemical, spectroscopic and X-ray crystallographic studies are presented.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1489 - 1503
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DOI: 10.3987/S-1981-02-1489
The Diterpenoids of Teucrium Species

Franco Piozzi*

*Institute of Organic Chemistry, Palermo University, Archirafi 20,Palermo, Italy


This review describes the major advances reported during the last five years on the chemistry of these terpenoids.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1505 - 1567
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DOI: 10.3987/S-1981-02-1505
Alkaloids from Plants of the Subfamily Wurmbaeoideae

Frantisek Santavy*

*Institute of Medical Chemistry, Medical Faculty, Palacky University, 775 15 Olomouc, Czech Republic


This review gives a survey of the most important papers on the isolation and chemistry of alkaloids (i.e. the tropolone alkaloids, their precursors, and the minor alkaloids) from plants of the subfamily Wurmbaeoideae, and of those of the biosynthesis of these compounds.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1531 - 1567
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DOI: 10.3987/S-1981-02-1531
Prenylflavonoids from the Root Bark of the Cultivated Mulberry Tree

Taro Nomura* and Toshio Fukai

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


Our present knowledge is reviewed of the chemistry of prenylflavonoid derivatives isolated from the root bark of the Japanese cultivated mulberry tree by our group. The oxidative cyclization is also discussed on the flavone derivatives having a free hydroxyl group at C-2’ position and γ,γ-dimethylallyl group at C-3 position.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1569 - 1617
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DOI: 10.3987/S-1981-02-1569
Cyclization and Cycloaddition Reactions of Heteroepins, Conjugated Seven-membered Heterocyclic Compounds

Toshio Mukai,* Tsutomu Kumagai, and Yoshiro Yamashita

*Department of Chemistry, Faculty of Science, Tohoku University, Aoba-ku, Ssendai 980-8578, Japan


This review describes the recent advances in the chemistry of heteroepins, especially the thermally and photochemically induced reactions of 1H-azepine, 1H-1,2-diazepines and 1,3-oxazepine derivatives as well as the synthesis of these heterocyclic compounds.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1621 - 1641
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DOI: 10.3987/S-1981-02-1621
13C-NMR Spectral Correlation for Simplified Structure Determination of Curamycins and Related Oligosaccharide Antibiotics

Nicholas F. Cappuccino, Ajay K. Bose,* James B. Morton, and Ashit K.Ganguly*

*Department of Chemistry and Chemical Engineering, Stevens Institute of Technology, Castle Point on the Hudson, Hoboken, NJ 07030, U.S.A.


13C NMR spectral analysis for structure determination of oligosaccharide antibiotics is discussed. The details of the structure of a pentasaccharide segment (pseudo-olgose A) of curamycin A is deduced on the basis of 13C NMR data.

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Review | Special issue | Vol 15, No. 2, 1981, pp. 1643 - 1658
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DOI: 10.3987/S-1981-02-1643
The Role of Cyclic Peroxides in the Reactions of 1,2-Diphenylcyclopropenes and Cyclobutenes with Singlet Oxygen

Caetan Vaz, Gary Griffin,* Siegfried Christensen, and David Lankin

*Department of Chemistry, University of New Orleans, New Orleans, LA 70148, U.S.A.


An array of cyclic peroxy intermediates, including dioxetanes, endo-peroxides and 1,2-dioxoles, are advanced as intermediates in the reactions of 1O2 with 1,2-diphenylcyclopropenes and cyclobutenes.

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118 data found. 91 - 118 listedFirst Previous