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. 3, No. 6, 1975
Published online:
■ Pschorr Reaction on 1-(2-Aminophenyl)-1,2,3,4-tetrahydro-2-methylisoquinoline
Tetsuji Kametani,* Shiroshi Shibuya, Ramamurthy Charubala, Manakkal S. Premila, and Bentwal R. Pai
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Diazotisation and Pschorr reaction of 6-amino-N-methyl-6,7-dimethoxy-1-(3,4-methylenedioxyphenyl)isoquinoline, gave besides the deaminated product, the corresponding 3,4-dihydroisoquinoline with N-demethylation and concomittant oxidation at the 1,2-position. 6-Amino-N-methyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)isoquinoline, under identical conditions gave, besides the deaminated product, a deep orange compound, which has been assigned the structure 3,4-dihydro-6,7,11,12-tetramethoxy-5-nitroazafluoranthene.
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■ A Radical Reaction of Tropone Tosylhydrazone Leading to 2-Tosylindazole
Katsuhiro Saito,* Takashi Toda, and Toshio Mukai
*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan
Abstract
Silver chromate oxidation of tropone tosylhydrazone sodium salt (I) afforded 2-tosylindazole (II). The reaction is considered to proceed via an hydrazyl radical intermediate (III). Under the same reaction conditions m-nitrobenzaldehyde tosylhydrazone sodium salt provided m-nitrobenzonitrile probably via m-nitrobenzylideneaminyl radical.
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■ Isoquinoline Alkaloids. IV. A Simple Entry to Oxoaporphine Alkaloids: Corunnine and Glauvine
Luis Castedo,* Rafael Suau, and Antonio Mouriño
*Departamento de Química Orgánica, Facultad de Ciencias, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain
Abstract
An efficient lead tetraacetate oxidation of glaucine (IV) to O-methylatheroline (III) is described. Simple heating of III afforded corunnine (I) instead of glauvine (II) as it had been previously reported.2
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■ A New Synthesis of Metathiazanone Derivatives via Intramolecular Pummerer Rearrangements
Isao Nagakura,* Hiroshi Oka, and Yoshihiro Nitta
*Department of Synthetic Development, Kohjin Co. Ltd., Shinbashi-machi, Fuji, Shizuoka 417, Japan
Abstract
A new synthesis of metathiazanone derivatives is described. The synthesis involves a novel, intramolecular Pummerer rearrangement.
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■ Structure Elucidation of Two New Tetrahydroprotoberberine Alkaloids, Corytenchine and Corytenchirine
Sheng-Teh Lu, Tsann-Long Su, Tetsuji Kametani,* Akira Ujiie, Masataka Ihara, and Keiichiro Fukumoto
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
The structures of two tetrahydroprotoberberines, corytenchine and corytenchirine, from Corydalis ochotensis Turcz were assigned to 3 and 12, respectively.
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■ Synthesis of Optically Active Ochotensanes
Jiro Imai, Yoshikazu Kondo,* and Tsunematsu Takemoto
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Treatment of l-(14S)-β- (Ia) and d-(14R)-β-canadine methochlorides (Ib) with organolithiums, lithium aluminium hydride, or sodium methylsulfinyl carbanion in tetrahydrofuran gave d- (IIa) and l-2,3-methylenedioxy-9,10-dimethoxyochotensanes (IIb), respectively. The structures of those have been proved by the results of the Hofmann degradation and spectral means. The cd spectra of IIa and IIb showed Davydov split extrema centered at 284 nm whose first Cotton effects corresponded to the absolute configurations.
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■ Chemistry of Zearalenone and Some of its Derivatives
Mohammed T. Shipchandler*
*Research Department, Commercial Solvents Corporation, Terre Haute, Indiana 47808, U.S.A.
Abstract
The chemistry of zearalenone (1), a metabolite of Gibberella zeae (Fusarium graminearum) is reviewed. Isolation, structure determination, chemical and physical properties, total syntheses, biosynthesis, and biological properties of zearalenone and some of its derivatives are discussed, and a summary of spectral and analytical methods used is presented.