Regular Issue

Vol. 14, No. 7, 1980

12 data found. 1 - 12 listed
Communication | Regular issue | Vol 14, No. 7, 1980, pp. 929 - 934
Published online:
DOI: 10.3987/R-1980-07-0929
Photochemically Induced 1,3-Dipolar Cycloadditions of 3-Amino-2H-azirines

Kurt Dietliker, Werner Stegmann, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


Irradiation of 3-(N-methylanilino)-2H-azirines in dimethoxyethane solution in the presence of dipolarophiles leads to five-membered heterocycles in 40-60% yield. A reaction mechanism via splitting of the C(2),C(3)-bond and formation of a nitrilio methanide which then undergoes a thermal 1,3-dipolar cycloaddition is reasonable.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 935 - 942
Published online:
DOI: 10.3987/R-1980-07-0935
Nitrogen-containing Carcinogenic Compounds. LXXXVII. Synthesis of Fluorinated and Trifluoromethylated Indolo[2,3-a]carbazoles and Indolo[2,3-a]acridines

Antonella Strappaghetti,* Geneviève Rabere, Arnaldo Fravolini, and Pierre Jacquignon

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


Within the general context of our research linked to mutagenesis and chemical carcinogenesis, compounds related to certain indolo[2,3-a]carbazoles and indolo[2,3-a]acridines bearing a fluorine atom or a trifluoromethyl group are described.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 943 - 945
Published online:
DOI: 10.3987/R-1980-07-0943
Grandirubrine, a New Tropoloisoquinoline Alkaloid

Mary D. Menachery and Michael P. Cava*

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.


Grandirubrine, a new alkaloid from Abuta grandifolia (Martius) Sandwith (Menispermaceae), has been assigned the tropoloisoquinoline structure I.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 947 - 950
Published online:
DOI: 10.3987/R-1980-07-0947
Transfer of a Functionalized Carbon-fragment via a (Substituted) N5,N10-Methylenetetrahydrofolic Acid Model. An Approach to D,L-Pyridindolol

Hans Bieräugel, Ronald Plemp, and Upendra K. Pandit*

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


Reaction of dl-tryptophan hydrochloride with 1-acetyl-3,4,4-trimethyl-2-[1,2-dihydroxyethyl]imidazolidine acetonide (2) leads to the formation of the β-carboline precursor of d,l-pyridindolol.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 951 - 953
Published online:
DOI: 10.3987/R-1980-07-0951
A Facile Synthesis of (±)-Camptothecin by Enamine Annelation

Tetsuji Kametani,* Tatsushi Ohsawa, and Masataka Ihara

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


A formal total synthesis of (±)-camptothecin (1) was achieved via the key steps of enamine annelation and subsequent dye-sensitized photooxygenation.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 955 - 958
Published online:
DOI: 10.3987/R-1980-07-0955
Reaction of N,N’-Thionyldiimidazole with Thiols: A Sulfur Transfer Reaction

Masaru Ogata,* Hiroshi Matsumoto, and Sumio Shimizu

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan


Reaction of N,N’-thionyldiimidazole with thiols effects the formation of disulfides and trisulfides. These results are rationalized by assuming that the thiols react with N,N’-thionyldiimidazole to produce the disulfides and N,N’-thiobisimidazole which subsequently reacts with the starting thiols to give the trisulfides.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 959 - 961
Published online:
DOI: 10.3987/R-1980-07-0959
Thermal Cyclization of Enamides

Takeaki Naito and Ichiya Ninomiya*

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


Enamides of N-aroylenamine type (2) and (7a), which contain an electron deficient aromatic ring, undergo facile cyclization not only photochemically but also thermally to afford the corresponding azaberbines (3), (4), (5), and (8) in good yields respectively.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 963 - 970
Published online:
DOI: 10.3987/R-1980-07-0963
Biotransformation of Isoquinoline Alkaloids with Rat Liver Microsomes

Tetsuji Kametani,* Naoaki Kanaya, Yohko Ohta, and Masataka Ihara

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


Optically active (+)-reticuline (1) was biotransformed into (-)-coreximine (2), (-)-scoulerine (3), (+)-isoboldine (4) and (-)-pallidine (5) with retention of the chirality by the incubation with rat liver microsomes. On the other hand, the racemate of reticuline formed the racemates of the above alkaloids on the some treatment. The S-adenosylmethionine was partially incorporated into the berberine bridge during the biotransformation of reticuline into the protoberberines.

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Communication | Regular issue | Vol 14, No. 7, 1980, pp. 971 - 974
Published online:
DOI: 10.3987/R-1980-07-0971
Structure of Demethyltubulosine: A Total Synthesis of (±)-10-Demethyltubulosine

Tozo Fujii,* Masashi Ohba, Alfred Popelak, Satyesh C. Pakrashi, and Esahak Ali

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


(±)-10-Demethyltubulosine (IV) has been synthesized from the tricyclic amino acid VI through the intermediates VII, VIII, and V. Identity of synthetic (±)-IV with natural (-)-demethyltubulosine unequivocally established the structure of this Alangium alkaloid.

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Report | Regular issue | Vol 14, No. 7, 1980, pp. 975 - 984
Published online:
DOI: 10.3987/R-1980-07-0975
Selenium Dioxide Oxidations in the β-Carboline Area

Olivia Campos, Mike DiPierro Michael Cain, Robert Mantei, Ali Gawish, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


The reaction of 1-ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 11 with selenium dioxide has resulted in the synthesis of the β-carboline alkaloids, 1-acetyl-3-methoxycarbonyl-β-carboline 14 and 1-acetyl-β-carboline 15. Application of this technology in a different series has resulted in a two step synthesis of canthin-6-one. The scope and/or limitations of the reaction of tetrahydro-β-carbolines with selenium dioxide are discussed.

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Review | Regular issue | Vol 14, No. 7, 1980, pp. 985 - 1032
Published online:
DOI: 10.3987/R-1980-07-0985
Reactions at C-9 of Acridine Derivatives. Part XXV

Stanislaw Skonieczny*

*Laboratory of Chemistry and Biochemistry of Antitumour Compound, Institute of Organic and Food Chemistry and Technology, Techinical University of Gdansk, 80-952 Gdansk 6, Poland


The kinetic data and mechanisms of the reactions occuring at the position 9 and/or 10 of the 9-substituted acridines have been reviewed. The mechanisms of hydrolysis and condensation reactions have been discussed and annelation effect considered where comparative data for the corresponding quinoline and pyridine derivatives were available. Some spactral and basicity data have been included to interpret the reaction mechanisms. Special attention has been payed to compounds of biological importance. The review falls into the following chapters according to the substituents undergoing substitution and/or types of the reactions being considered.

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Review | Regular issue | Vol 14, No. 7, 1980, pp. 1033 - 1043
Published online:
DOI: 10.3987/R-1980-07-1033
Reissert Compounds Derived from Diazaaromatic Systems

Frank D. Popp*

*Department of Chemistry, University of Missouri-Kansas City, Kansas City, Missouri 64110, U.S.A.


The preparation and reactions of Reissert compounds from phthalazine, naphthyridines, phenanthrolines, and ellipticine are discussed in detail. Attempts to extend Reissert compound formation to other diaza systems are also discussed.

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12 data found. 1 - 12 listed