HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 14, No. 7, 1980
Published online:
■ 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
Abstract
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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■ 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
Abstract
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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■ 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.
Abstract
Grandirubrine, a new alkaloid from Abuta grandifolia (Martius) Sandwith (Menispermaceae), has been assigned the tropoloisoquinoline structure I.
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■ 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
Abstract
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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■ A Facile Synthesis of (±)-Camptothecin by Enamine Annelation
Tetsuji Kametani,* Tatsushi Ohsawa, and Masataka Ihara
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
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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■ 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
Abstract
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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■ Thermal Cyclization of Enamides
Takeaki Naito and Ichiya Ninomiya*
*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan
Abstract
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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■ 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
Abstract
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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■ 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
Abstract
(±)-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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■ 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.
Abstract
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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■ 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
Abstract
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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■ Reissert Compounds Derived from Diazaaromatic Systems
Frank D. Popp*
*Department of Chemistry, University of Missouri-Kansas City, Kansas City, Missouri 64110, U.S.A.
Abstract
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.