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. 9, 1976
Published online:
■ The Final Product of Photocyclization of 3,4-Bisarylmethylenedihydo-2(3H)-furanone
Takefumi Momose,* Ken-ichi Kanai, and Takeshi Nakamura
*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan
Abstract
Irradiation of 3,4-bisarylmethylenedihydro-2(3H)-furanone afforded selectively β-apolignan, but was accompanied by subsequent transformation into benzobicyclo[3.1.0]hex-2-ene system via novel degenerate photorearrangement.
Published online:
■ Simple Synthesis of Quinazolone Alkaloids Arborine and Rutecarpine through Iminoketene
Tetsuji Kametani,* Chu Van Loc, Terumi Higa, Masuo Koizumi, Masataka Ihara, and Keiichiro Fukumoto
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
The iminoketene (3) generated in situ from the sulfinamide anhydride (2), prepared from anthranilic acid (1), reacted with several types of amide to give quinazolin-4-ones (12 - 14). This reaction was applied to a total synthesis of arborine (19) and rutecarpine (22).
Published online:
■ Syntheses of 2-Pyrone Derivatives
Yoshinori Tominaga, Yoshiro Matsuda, and Goro Kobayashi*
*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan
Abstract
2-Pyrone derivatives were synthesized by the reaction of monoketone compounds with ketenethioacetals in the presence of powdered potassium hydroxide as a base.
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■ A New Synthesis of Benzo[c]phenanthridine Derivative
Hideo Iida,* Kohkichiro Takahashi, and Toyohiko Kikuchi
*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
4-Substituted isocarbostyril derivative (V) was reduced with lithium aluminum hydride to give the 1,2-dihydro-4-substituted isoquinole which was heated with hydrochloric acid to give two cis-hexahydrobenzo[c]phenanthridine derivatives (VI) and (VII or VIII).
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■ A Transformation of 7-Azapteridines into 6-Azapurines (Imidazo[4,5-e]-as-triazines)
Fumio Yoneda,* Mitsuko Kawamura, Tomohisa Nagamatsu, Kazuo Kuretani, Akio Hoshi, and Masaaki Iigo
*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan
Abstract
Treatment of 6-substituted 3-methyl-7-azalumazines and 6-substituted 1,3-dimethyl-7-azalumazines (fervenulins) with alcoholic sodium hydroxide caused a benzylic acid type rearrangement followed by decarboxylation and oxidation by air to give the respective 5-methyl- and 5,7-dimethyl-5H-imidazo[4,5-e]-as-triazine-6(7H)-ones.
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■ The Chemistry of 1,2-Diazepines
Michel Nastasi*
*Ecole Nationale Supérieure de Chimie de Mulhouse, Université du Haut-Rhin, 68093 Mulhouse, France
Abstract
Review articles on 1,2-, 1,3- and 1,4-diazepines (1, 2), benzodiazepines (3) and 1,3-diazepines (4) have appeared previously. The present review covers the literature on l,2-diazepines from 1966 to early 1975.