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. 2, No. 3, 1974
Published online:
■ Synthesis of New Cinchona and Quinine Analogs
W. Nico Speckamp* and Jan Dijkink
*Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129,1018 WS Amsterdam, The Netherlands
Abstract
The total synthesis of quinine analogs 4a and 4b is described. The quinuclidine part in the naturally occurring compound has been replaced by the l-azaadamantane nucleus.
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■ The Synthesis of (2H)-Pyrrole-1-Oxides by Ring Contraction
Rudolph A. Abramovitch* and Berkeley W. Cue, Jr.
*Department of Chemistry, University of Alabama, Box 870336, University, Tuscaloosa, Alabama 35478-0336, U. S. A.
Abstract
The ring contraction of 2-azido-3-alkylpyridine-1-oxides gives 2-alkyl- 2-cyano-(2H)-pyrrole-1-oxides in good yield. Possible ambiguities in the nmr spectra of these compounds have been resolved.
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■ Reductive Cyclization of α-(6-Nitroveratrylidene)-γ-butyrolactone with Triethyl Phosphite
Frank F. Ebetino, Keiichiro Fukumoto, and Tetsuji Kametani*
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
The reaction of triethyl phosphite with α-(6-nitroveratrylidene)-γ-butyrolactone (5) produced a mixture of 3,4-dihydro-7,8-dimethoxy[1,3]oxazino[3,4-a]indol-1-one (8), 2,3-dihydro-6,7-dimethoxyfuro[2,3-b]quinoline (9) and ethyl 5,6-dimethoxyindole-2-carboxylate (10).
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■ Reaction of Methyl 2,3-Dihydro-3-methyl-2-methylenebenzothiazole-α-dithiocarboxylate with Dimethyl Acetylenedicarboxylate
Goro Kobayashi,* Yoshiro Matsuda, Yoshinori Tominaga, and Kazumichi Mizuyama
*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan
Abstract
Treatment of methyl 2,3-dihydro-3-methyl-2-methylenebenzothiazole-α-dithiocarboxylate with dimethyl acetylenedicarboxylate in dimethylformamide resulted in a Diels-Alder cycloaddition which were followed by desulfurization. This product is a spiro-compound 2,3-dimethoxycarbonyl-4-methylthio-2,4-cyclopentadiene-1-spiro-2-(2,3-dihydro-3-methylbenzothiazole).
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■ Studies on Ketene and Its Derivatives. LXIV. Reaction of Diketene with Acridine N-Oxide
Tetsuzo Kato,* Takuo Chiba, and Mohsen Daneshtalab
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Acridine N-oxide reacts with diketene to give 9-acetonylacridine. A probable mechanism is discussed.
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■ Oxidative Functionalization at the Benzylic Carbon of α-Substituted Indoles with Benzoyl Peroxide
Masato Aiura and Yuichi Kanaoka*
*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Abstract
On reaction with benzoyl peroxide 1 followed by treatment with a nucleophile, oxidative functionalization can be achieved at the benzylic carbon of α-substituted indoles 2.
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■ A Synthesis of (±)-Dihydrodeoxyepiallocernuine by Application of a Facile Hofmann-Loeffler Type of Photocyclization
Yoshio Ban,* Masayuki Kimura, and Takeshi Oishi
*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Abstract
Isopelletierine (3a) which is proved to be a precursor in the biosynthesis of cernuine (1), was converted into the quinolizidine (10a), whose N-chloro derivative (10b) was irradiated with a 300W high pressure mercury lamp in ether in the absence of strong acid to readily afford the entitled compound (2) as the free base with no base treatment.
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■ Photoalkylation of Niketamide and Its Analogs
Ichiya Ninomiya,* Okiko Yamamoto, and Toshiko Kiguchi
*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan
Abstract
Niketamide (I) and its isomeric analogs (II and III) were irradiated in methanol to afford a variety of photoalkylated products (IV-XI) , which reflected a pattern of orientation of the photoaddition.
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■ Heterocycles. IX. Synthesis of 1,5-Diphenyl-1H-imidazo[1,5-b]-s-triazoles
Kanji Meguro* and Yutaka Kuwada
*Central Research Division, Takeda Chemical Industries, Ltd., 17-85 Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan
Abstract
Cyclization of 3-benzamidomethyl-4-phenyl-4H-1,2,4-triazoles (IVa,b) with polyphosphate ester gave 1,5-diphenyl-1H-imidazo[l,5-b]-s-triazole derivatives (Va,b).
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■ A Facile Synthesis of the Spirobenzylisoquinolines and the Spirobenzylcarbolines
Tetsuji Kametani,* Yoshiro Hirai, Hiromitsu Takeda, Masahiro Kajiwara, Tamiko Takahashi, Fumio Satoh, and Keiichiro Fukumoto
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
1’,2,2’,3,3’,4’-Hexahydro-5,6,6’,7’-tetramethoxy-1-ketospiro[indene-2,1’-isoquinoline] (IVa) and its 7’-benzyloxy analogue (IVb) are synthesized from 3,4-dihydro-1-(4,5-dimethoxybenzocyclobutenyl)isoquinolines (I). 1-Ketospiro[indene-2,1’-β-carbolines] (XIa and XIb) are also obtained by the same method from the corresponding benzocyclobutene derivatives (IXa and IXb).
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■ The Coumarin from Ekebergia senegalensis: A Revision
Pietro Venturella, Aurora Bellino, and Franco Piozzi*
*Dipartimento di Chimica Organica, Università di Palermo, Via Archirafi 20 90123 Palermo, Italy
Abstract
The structure of the coumarin from E. senegalensis is revised to 4-methoxy-5-methylcoumarin (II).
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■ Syntheses of Benzodiazocines
Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, and Kikuo Wakisaka
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Introduction of an additional nitrogen atom into a benzazocine (6,7-benzomorphan) ring gives a benzodiazocine (azabenzomorphan). The syntheses of twelve types of benzodiazocines are reviewed and some of their analgesic properties are discussed.
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■ Synthesis of Nitro-, Amino-, and Polycyclic Furans
Frank F. Ebetino*
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
The synthesis of a number of 5-nitro- and 5-amino-2-furaldehyde derivatives is described in this review. Cyclization of an aminofuran to a furo[2,3-b]pyridine and reductive cyclization of substituted butyrolactones to furo[2,3-b]quinolines and indoles are also dis- cussed.