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. 6, 1978
Published online:
■ Studies on the Synthesis of 13-Methyltetrahydroprotoberberine Derivative
Hideo Iida,* Mamoru Narimiya, Nobuko Katoh, Hiroji Ina, and Toyohiko Kikuchi
*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
4-Methylated isocarbostyril derivative (VII) was reduced with lithium aluminum hydride, followed by an acidic treatment to give the trans-13-methyltetrahydroprotoberberine (VIII).
Published online:
■ The Syntheses of Azatropolones
Takehiro Sano,* Yoshie Horiguchi, and Yoshisuke Tsuda
*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
Abstract
Azatropolones, the compounds of new ring system, were synthesized by thermal cleavage of 2-azabicyclo[3.2.0]hept-6-one derivatives, and their chemical and spectral properties were described. Particularly azatropolones were susceptible to solvolysis furnishing pyridine-2-carboxylates.
Published online:
■ Ring Transformation of Uracils to 2-Pyridones. Hydrolysis of 6-(2-Dimethylaminovinyl)uracils
Shigeo Senda,* Kosaku Hirota, Tetsuji Asao, and Yoshio Abe
*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan
Abstract
Hydrolysis of 1,3-disubstituted 6-(2-dimethylaminovinyl)uracil derivatives (I) in aqueous sodium hydroxide caused a novel ring transformation giving 2-pyridone (II) along with 4-methylenepyrimidine (III) or the degradation product (IV or V).
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■ Kuwanon D, New Isoprenoid Flavanone from the Root Bark of the Cultivated Mulberry Tree (Morus Alba L.)
Taro Nomura,* Toshio Fukai, and Masa Katayanagi
*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan
Abstract
From the benzene extract of the root bark of the cultivated mulberry tree (a variety of Morus alba L.), a novel isoprene-substituted flavanone, kuwanon D, was isolated whose structure was shown to be I on the basis of spectral data.
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■ Synthesis of D-Isoepiallomuscarine
Pen-Chung Wang, Zenon Lysenko, and Madeleine M. Joullié*
*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.
Abstract
D-Isoepiallomuscarine is prepared in high yield from α-D-glucose by way of regio-, and stereo-selective epoxide ring opening using sodium phenyl selenide.
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■ Reaction of Enamine Esters with Diazonium Salts. A Facile One-Pot Synthesis of Imidazo[1,2a]azacycloalkanes
Chananjah B. Kanner and Upendra K. Pandit*
*Organic Chemistry Laboratory, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
Abstract
Reaction of β-aminoacrylic esters with benzenediazonium fluoroborate, followed by treatment with triethyl amine leads to the formation of imidazole derivatives.