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. 19, No. 5, 1982
Published online:
■ A General Synthesis of Indolo[2,3-a]quinolizine from a Symmetrical Starting Material, cis-Δ4-Tetrahydrophthalic Acid Anhydride
Tetsuji Kametani, Toshio Suzuki, Shinko Kamada, and Katsuo Unno
*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan
Abstract
A general synthesis of indolo[2,3-a]quinolizine derivatives (12) and (13) has been achieved by a condensation of tryptamine with the aldehyde (11) derived from a symmetrical starting material, cis-Δ4-tetrahydrophthalic acid anhydride (2).
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■ Hydrazones as New 4-Electrons Three Atomic Centers in Cycloaddition Reactions: A Novel Approach for the Synthesis of Pyrazole Derivatives
Yehia A. Ibrahim, Sadek E. Abdou, and Sami Selim
*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt
Abstract
Aromatic aldehydes and acetophenone phenylhydrazones undergo cycloaddition reactions with maleimides to give the pyrrolo[3,4-d]pyrazole derivatives via a novel pericyclic reaction involving easily accessible 4π-electrons neutral three atomic centers.
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■ Acridone Alkaloid. III. Structure of Glycofoline, a New Mototerpenoid Acridone Alkaloid from Glycosmis citrifolia (Willd.) Lindl
Tian-Shung Wu and Hiroshi Furukawa
*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan
Abstract
A new monoterpenoid acridone alkaloid glycofoline (1) was isolated from the root- and stem-bark of Glycosmis citrifolia (Willd.) Lindl., and the structure was elucidated on the basis of the spectral data and a chemical transformation.
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■ Selective Cleavage of Unsymmetrical 2,2-Spiro-1,3-dioxolanes I. Ketalization of 5-Bromo-3-methoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]furan-4-one and Its Analogs
Makiko Sakai
*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan
Abstract
Reaction of 2-bromocyclohexanones fused with an aromatic or heteroaromatic ring (1-4) with epibromohydrin or 3-bromo-1,2-propanediol gave two (a and b) or four (a, b, c, and d) isomers of the corresponding 2,2-spiro-4-bromomethyl-1,3-dioxolanes 5-8, respectively. The stereochemistry of the reactions is discussed.
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■ 1- and 2-Chloromorphine. Halogenation of Morphine meta to the Free Phenolic Hydroxyl Group
Bajrang Bali Singh, Ranjit Singh Chauhan, Kattigari Madhava Madyastha, Surendra P. Bhatnagar, Kenneth L. Kirk, and Ulrich Weiss
*Laboratory of Chemical Diseases, National Institute of Diabetes and Digestive and Kidney, National Institute of Health, Bethesda, MD 20892, U.S.A.
Abstract
Treatment of morphine in aqueous HCl at 70° with KIO3 yields a monochloromorphine, identified as 1-chloromorphine by spectroscopic means and by the fact that it, and its methyl ether 1-chlorocodeine, are different from 2-chloromorphine and 2-chlorocodeine prepared from 2-aminomorphine of unequivocally established structure. Formation of 1-chloromorphine and the previously known 1-bromomorphine involves entry of the halogen into the position meta to the free phenolic hydroxyl. Possible mechanistic interpretations of this unusual orientation are discussed.
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■ Structure of Cristadine; a New Benzylisoqunoline Alkaloid
Motoharu Ju-ichi, Yukari Fujitani, and Hiroshi Furukawa
*Faculty of Pharmaceutical Science, Mukogawa-Women’s University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan
Abstract
Cristadine (I), a new benzylisoquinoline alkaloid, was isolated from the leaves of Erythrina crista-galli Linn. (Leguminosae) and its structure was elucidated by chemical and spectral studies as (I).
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■ On the Structure of Ajmalinol
Ari Koskinen and Mauri Lounasmaa
*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland
Abstract
The recently proposed structure for ajmalinol cannot be correlated with the reported 13C NMR spectral data.
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■ Model Studies in the Vinoxine Series
Joan Bosch, Miguel Feliz, and Ma Lluïsa Bennasar
*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain
Abstract
The synthesis of 1a, fundamental tetracyclic framework of vinoxine, and its 16-methoxycarbonyl substituted analogue 1b by mercuric acetate oxidation of appropriate 1-(4-pyridylmethyl)indoles is described.
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■ Syntheses of (—)-9-Dimethylcephaeline and (—)-10-Demethylcephaeline
Tozo Fujii and Masashi Ohba
*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan
Abstract
The synthesis of (—)-9-demethylcephaeline (I) has been accomplished by reduction of (+)-O,O-dibenzyl-9-demethylpsychotrine (Xla) followed by debenzylation of the resulting (—)-tetrahydroisoquinoline derivative XIIa. A parallel synthesis starting with (+)-O,O-dibenzyl-10-demethylpsychotrine (Xlb), prepared from the (—)-tricyclic amino ester Vlllb through the (—)-amino acid IXb and the (—)-amide Xb, gave (—)-10-demethylcephaeline (II).
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■ A Review on the Partial and Total Syntheses of Thiasteroids
Sukuru Raghu Ramadas, Pamidi Chinna Chenchaiah, Nizal S. Chandra Kumar, Mokkapati Vijaya Krishna, Pathangi Sampath Srinivasan, Vadapalli V. S. Kameswara Sastry, and Jatla Appa Rao
*Department of Chemistry, Indian Institute of Technology, Madras, 600 036, India
Abstract
This review describes the recent progress achieved in the partial and total syntheses of thiasteroids as well as in the total syntheses of pyrazole and isoxazole analogues of steroids with sulfur atom in various positions of the steroid nucleus.
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■ Absorption Spectra of Phenothiazines
Sayeed Saraf, Muhammad Akram Khan, and Saleh Al-Mousawi
*Department of Chemistry, Faculty of Science, University of Kuwait, Safat 13060, P.O. Box 5969, Kuwait
Abstract
The ultra-violet absorption spectra of phenothiazine derivatives are reviewed.