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. 3, 1976
Published online:
■ Reaction of 3-Bromo-4-nitroquinoline 1-Oxide with Enamines. A Novel Cyclization Reaction to Furo[3,2-b]quinoline System
Hiroshi Noda, Teruo Yamamori, Mitsutaka Yoshida, and Masatomo Hamana*
*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan
Abstract
3-Bromo-4-nitroquinoline 1-oxide (1) reacts with 1-morpholinocyclohexene at room temperature in chloroform to give 10-nitrotetrahydrobenzofuro[3,2-b]quinoline (2) in high yield via the primary adduct of the 1,3-dipolar cycloaddition reaction. The scope of this type of reaction is widespread, but similar reactions of 3-bromo- and 3-bromo-4-methoxyquinoline 1-oxides afford 2-(2-oxocyclohexyl)-3-morpholinoquinoline (14a) and its 4-methoxy derivative (14b).
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■ Photoreductive Cyclization of 5-Nitro-6-styryl(or Anilino)uracil Derivatives to Pyrrolo[3,2-d]pyrimidine and Alloxazine Derivatives
Shige Senda,* Kosaku Hirota, and Mikio Takahashi
*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan
Abstract
Irradiation of 5-nitro-6-styryluracil and 6-anilino-5-nitrouracil derivatives causes a photoreductive cyclization to give the pyrrolo[3,2-d]pyrimidines and the alloxazines, respectively.
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■ Photoisomerisation of trans-4b,10b,11,12-Tetrahydrobenzo[c]phenanthridin-6(5H)-one to the cis-Isomer
Ichiya Ninomiya,* Toshiko Kiguchi, Okiko Yamamoto, and Takeaki Naito
*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo658, Japan
Abstract
Irradiation of some B/C-trans-benzo[c]phenanthridones substituted with an electron-withdrawing group such as ester and nitrile caused isomerisation to afford the corresponding cis-lactams.
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■ Sciadenine, a New Bisbenzylisoquinoline Alkaloid from Sciadotenia toxifera
Keiichi Takahashi, 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
Sciadenine, a new alkaloid from Sciadotenia toxifera Krukoff and A. C. Smith (Menispermaceae), has been assigned the head-to-tail bisbenzylisoquinoline structure I.
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■ Photochemistry of Isonicotinohydrazide and Its Analogs in Alcohol
Ichiya Ninomiya* and Okiko Yamamoto
*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan
Abstract
Irradiation of isonicotinohydrazide (Iγ) and its analogs (Iα and Iβ) in alcohols, i.e., methanol, ethanol, isopropyl alcohol, and benzyl alcohol afforded two types of photoproducts, that is, the alkylidenehydrazides (II, IV, VI) and the 2’-(2-hydroxyethyl)hydrazides (III, V, VII), except the cases of the hydrazides having ortho-amino and methoxyl groups which yielded the N-N bond fission products.
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■ Recent Chemical Progress in Berberine Alkaloids
Tetsuji Kametani,* Masataka Ihara, and Toshio Honda
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Chemical progress of berberine alkaloids over the past decade has been reviewed.
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■ Biosynthesis of Secoiridoid Glucosides
Hiroyuki Inouye,* Shinichi Ueda, and Yoshio Takeda
*Faculty of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan
Abstract
In the present review the biosynthetic pathways of sweroside, morroniside and oleuropein type secoiridoid glucosides through mevalonic acid (MVA), geraniol, deoxyloganin, loganin etc. are outlined. The biosynthesis of alkaloidal glucosides, which can be regarded as kinds of secoiridoids, is also briefly described.
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■ Isoxazolin-5-ones, Chemistry and Biology of a New Class of Plant Products
Fernand Lambein, Yu-Haey Kuo, and Roger Van Parijs*
*Biochemical Institute, University of Ghent, Ledeganckstraat, Ghent, Belgium
Abstract
A group of uv-sensitive heterocyclic compounds characterized as isoxazolin-5-ones were found in some legume seedlings. Their isolation, purification and structural identification are explained. With emphasis on the particular properties of the natural products — chemical and photochemical degradation — the chemistry of N-substituted isoxazolin-5-ones is reviewed. The second part of this paper deals with the distribution, metabolism and with some biological aspects of the title compounds. Their possible origin and function are discussed.
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■ Norditerpene Dilactones from Podocarpus Species
Shô Itô* and Mitsuaki Kodama
*Department of Chemistry, Graduate School of Science, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Chemistry of biologically active norditerpene dilactones isolated from Podocarpus species are discussed with emphasis on the relationship between their structures and spectroscopic and other physical properties as well as their biological activities. Also briefly discussed are tetranorditerpene dilactones isolated from a mould.