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. 4, No. 6, 1976
Published online:
■ Synthesis of a Cyrokinin Metabolite
James D. McChesney* and Russell Buchman
*Department of Medicinal Chemistry, University of Kansas, 4070 Malott Hall, Lawrence, Kansas 66045-2506, U.S.A.
Abstract
A number of plant tissues convert approximately 20-25% of the cytokinin, 6-benzylaminopurine, into a stable, long-lived derivative previously identified tentatively as 7-glucofuranosyl-6-benzylaminopurine. This substance has been synthesized by an unambiguous route and shown not to be identical with the long-lived metabolite. Synthesis and comparison of 7-β-glucopyranosyl-6-benzylaminopurine with the metabolite proves that to be the structure of the metabolite instead.
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■ Structure of a New Bisbenzylisoquinoline Alkaloid, Lindoldhamine
Sheng-Teh Lu* and Ih-Sheng Chen
*School of Pharmacy, Kaohsiung Medical College, 100 Shih Chuen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.
Abstract
The structure of lindoldhamine, isolated from the leaves of Lindera oldhamii Hemsl.(Lauraceae), has been established as (1), by spectral data and chemical degradations.
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■ Photolysis of Some Quinoxaline-1,4-dioxides. A Method of Structural Assignment
Adil A. Jarrar, Safi S. Halawi, and Makhluf J. Haddadin*
*Department of Chemistry, American University of Beirut, Beirut, Lebanon
Abstract
The structures of some 2,3,6(7)-trisubstituted quinoxaline-1,4-dioxides were assigned through their photolytic rearrangement into 1,3,5(6)-trisubstituted benzimidazolones. Photolysis of related quinoxaline-1,4-dioxides demonstrated the generality of the rearrangement.
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■ Synthesis of Yenhusomine and Yenhusomidine
Hiroshi Irie,* Akiko Kitagawa, Atsushi Kuno, Junko Tanaka, and Noriko Yokotani
*Faculty of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan
Abstract
Yenhusomine and yenhusomidine, previously isolated from Corydalis ochotensis Turcz. were synthesised by reduction of synthetically obtained oxo-yenhusomine with sodium borohydride in a regio- and stereo-selective manner.
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■ The Synthesis of Japonine
Pietro Venturella, Aurora Bellino, Franco Piozzi,* and M. Luisa Marino
*Dipartimento di Chimica Organica, Università digli Studi di Palermo, Via Archirafi 20 90123 Palermo, Italy
Abstract
The total synthesis of japonine [I] is described. Methylation of the 3-hydroxy-4-quinolones [II] and [III] with methyl iodide in N,N-dimethylformamide afforded 3-methoxy-1-methyl-4-quinolones, whereas treatment with methyl p-toluenesulphonate or diazomethane gave 3,4-dimethoxyquinolines.
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■ Intra- and Inter-molecular Photoreactions of N-Chloroacetyl Derivatives of Dimethylaminophenethylamines and Dimethylaminobenzylamines in Both Acidic and Basic Solutions
Naganori Numao and Osamu Yonemitsu*
*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan
Abstract
Photocyclization of N-chloroacetyl derivatives of dimethylaminophenethylamines and dimethylaminobenzylamines were examined. Intramolecular photoreactions little affected by acid gave azepinones (V, VI) and a cage compound (VIII), while novel diazametacyclophanes (IX, XII) were obtained intermolecularly, which was strongly depressed by acid. These results suggest that the photoreactions involve the singlet excited state of the dimethylaniline moiety.
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■ Pictet-Spengler Condensations in Refluxing Benzene
J. Sandrin, D. Soerens, L. Hutchins, E. Richfield, F. Ungemach, and J. M. Cook*
*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.
Abstract
A variety of 1,3-disubstituted-l,2,3,4-tetrahydro-β-carbolines have been synthesized utilizing a Pictet-Spengler condensation in a non-aqueous system, without the addition of acid. This new method affords significantly increased yields of the 1,3-disubstituted-1,2,3,4-tetrahydro-β-carbolines compared to aqueous acid/methanol systems, especially for acid labile aldehydes.
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■ Selenium Analogs of Naturally Occurring Products. II
Léopold Laitem, Léon Christiaens,* and André Welter
*Heterocyclic Chemistry, Institute of Organic Chemistry, University of Liège, Sart Tilman B6, B-4000 Liege, Belgium
Abstract
Selenium analogs of desmethoxyharmaline (XII), harmine (III) and hexadehydro yohimbane (IV) have been synthesised.
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■ The Optical Resolution of (±)-Galanthamine
Tetsuji Kametani,* Manakkal Sivaraman Premila, and Keiichiro Fukumoto
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
(±)-Galanthamine has been resolved using optically active di-p-toluoyltartaric acid.
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■ Utility of Heterocyclic Diazo Compounds in Organic Synthesis
Miha Tisler* and Branko Stanovnik
*Department of Chemistry, University of Ljubljana, 61000 Ljubljana, Yugoslavia
Abstract
This review summarizes various transformations of heterocyclic diazo compounds and diazonium salts, in particular cyclizations, condensations, additions to multiple bonds, transformations involving elimination of the diazo group, rearrangements and reactivity of some heterocyclic systems as masked diazonium compounds.