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. 9, No. 8, 1978
Published online:
■ Gilletine, a New Bisbenzylisoquinoline Alkaloid from Triclisia gilletii
Daniel Dwuma-Badu, John S. K. Ayim, Albert N. Tackie, Philip D. Owusu, Joseph E. Knapp, David J. Slatkin, and Paul L. Schiff, Jr.*
*Department of Pharmaceutal Science, School of Pharmacy, University of Pittsburgh, Pittsburgh, PA 15261, U.S.A.
Abstract
Gilletine (1), a new alkaloid from extracts of the leaves of Triclisia gilletii (Menispermaceae), was characterized as a dibenzodioxin bisbenzylisoquinoline base by physicochemical data and conversion to O,O-dimethylcocsulinine (3).
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■ The Reaction of Benzylideneacetone with Ethylenediamine. Evidence for the Production of Two Isomeric 1,4,8,11-Tetra-azacyclotetradeca-4,11-dienes
Peter W. R. Caulkett, David Greatbanks, Ralph W. Turner,* and John A. J. Jarvis
*Department of Chemistry, ICI Pharmaceuticals, Mereside, Alderley Park, Macclesfield, Cheshire, SK10 4TG, U.K.
Abstract
The reduction of the 1,4,8,11-tetra-azacyclo-tetradeca-4,11-diene product from benzylidene acetone and ethylenediamine to give two isomeric 1,4,8,11-tetra-azacyclotetradecanes is reported. X-ray data for the condensation product of the minor isomer and glyoxal is described. The assignment of the transoid structure, (9) to the minor isomer suggests that the initial tetra-azacyclotetradeca-4,11-diene is a mixture of the diastereoisomers (2) and (3).
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■ Cimiciphytine and Norcimiciphytine — New Bisindole Alkaloids from Haplophyton cimicidum (Apocyanaceae)
M. V. Laksmikantham, Michael J. Mitchell, and Michael P. Cava*
*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.
Abstract
Cimiciphytine and norcimiciphytine, two new lactonic indole alkaloids isolated from Haplophvton cimicidum, have been assigned the aspidosperma-canthinone bisindole structures 3 and 4, respectively.
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■ Studies on the Synthesis of Bisindole Alkaloids. XIV. Enzyme Catalysed Formation of Leurosine
Kenneth L. Stuart, James P. Kutney,* and Brian R. Worth
*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada
Abstract
Enzyme catalysed oxidation of 3’,4’-dehydrovinblastine using either horseradish peroxidase or cell free extracts from Catharanthus roseus plants provided leurosine, suggesting that the latter is in fact a natural product.
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■ Photocyclization of Heterocyclic Acylanilides
Ichiya Ninomiya,* Toshiko Kiguchi, and Takeaki Naito
*Kobe Women‘s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan
Abstract
N-α,β-Unsaturated acylanilides, which contain various heterocyclic rings in their acyl groups, i.e., α-pyrone, α-fnranone, α- and β-furans, and an ortho-substituent on the benzene ring, were found to undergo photocyclization to afford various products depending upon a heterocycle, and an ortho-substituent which brought about smooth photocyclization.
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■ Cyclization Reaction of N-Substituted Mandelhydrazide with Formaldehyde
Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Nagatoshi Wagatsuma, Toshitaka Kohagisawa, and Hitoshi Inoue
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Acid-catalysed cyclisation of N-substituted mandelhydrazides II and X with paraformaldehyde gave hexahydro-1,2,4,5-tetrazine derivatives. Furthermore, the acetyl group on the nitrogen rearranged to alcoholic oxygen during the reaction of X to give VI.
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■ Molecular Structure of Azines of 3-Acetyl-4-hydroxy-2-methoxy-4-phenylcrotonic Acid Lactones
Takushi Kurihara,* Yasuhiko Sakamoto, Masanobu Mori, and Toshimasa Sasaki
*Faculty of Pharmaceutical Science, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
Abstract
Reaction of 3-acetyl-4-hydroxy-2-methoxy-4-phenylcrotonic acid lactones (2a,b) with hydrazine dihydrochloride (3) gave a mixture of azines (5a,b and 6a,b), and these structures were definitely determined by crystallographic analyses of 5b and 6b.
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■ Synthesis of Methyl (R,S)-Lichensterinate
Seppo I. Pennanen*
*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland
Abstract
The methyl ester of (R,S)-lichensterinic acid was synthesized from methyl α-ketopalmitate and 1-diethylaminopropyne in three steps in 58% overall yield.
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■ A Novel (E)-2-Oxoindolin-3-ylideneacxetone Dimer
Akinori Kubo,* Tatsuya Nakai, Toshikazu Nozoye, Akiko Itai, and Yoichi IItaka
*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan
Abstract
The dimerization reaction of (E)-2-oxoindolin-3-ylideneacetone (1) is described. The structure and stereochemistry of a novel dimeric product (4) were determined by PMR, CMR analyses and confirmed by X-ray analysis.
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■ Pyrroloquinolines III. Pyrrolo[3,4-b]quinolines
Misbahul Ain Khan* and João Ferreira da Rocha
*Seção de Quimica, Instituto Militar de Engenharia, Urca, 20.000 Rio de Janeiro, RJ, Brazil
Abstract
In the present review various routes for the synthesis of the pyrrolo[3,4-b]quinoline system, its reactions, and the spectral data for some of the derivatives of this system are presented.
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■ The Spiroindolenine Intermediate, a Review
Frank Ungemach and James M. Cook*
*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.
Abstract
The Pictet-Spengler reaction has been employed to prepare 1,2,3,4-tetrahydro-β-carbolines for many years and is presumed to go through the spiroindolenine intermediate (XIX). A review of the evidence for this mechanism is presented.