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. 12, No. 8, 1979
Published online:
■ Synthesis of a Novel Heterocyclic System, Indolo[2’,3’:5,6][1,2,4]triazino[2,3-a]benzimidazole
William A. Romanchick and Madeleine M. Joullié*
*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.
Abstract
The incorporation of both the benzimidazole and triazinoindole moieties in a new ring system has been accomplished via the condensation of 1,2-diaminobenzimidazoles with various isatins. The alkylation of one of the products (4a) was investigated.
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■ A 1,3-Dipolar Cycloaddition and 1,3-Addition of 2-Methylfuran
Lubor Fisera,* Jaroslav Kovác, and Jaroslava Poliaciková
*Department of Organic Chemistry, Faculty of Chemical Technology, Slovak University of Technology, SK-812 37 Bratislava, Slovakia
Abstract
A 1,3-dipolar cycloaddition reaction of 2-methyl- and 2-ethylfurans with C-bezoyl-N-phenylnitron has been carried out. A 1,3-dipolar cycloaddition product and a non-cyclic addition product were obtained, under the different molar ratio of the starting components.
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■ Novel Convenient Synthesis of 1,4-Diazepines; 6-Alkoxy-5,6-dihydro-4H-pyrrolo[1,2-a]thieno[3,2-f]-1,4-diazepine-4-ones
S. Rault, M. Cugnon de Sévricourt, and M. Robba*
*Centre d’Etudes et de Recherche sur le Médicament de Normandie, U. F. R. des Sciences Pharmaceutiques, Université de Caen, 1, rue Vaubénard, 14032 Caen Cedex, France
Abstract
Cyclisation of N-(3-cyano-2-thienyl)-2-formyl pyrrole with alcohols in sodium hydroxide solution resulted in the formation of the corresponding 6-alkoxy-5,6-dihydro-4H-pyrrolo[1,2-a]thieno[3,2-f]-1,4-diazepine-4-ones.
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■ Synthesis of Benzoxanthone Derivatives
Tetsuzo Kato,* Jun Nakano, and Nobuya Katagiri
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Benzoxanthone derivatives were prepared by photo-induced Fries rearrangement of aroyloxynaphthalenes, followed by alkali treatment.
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■ Synthesis of an Alkaloid Onychine and Related Compounds: Revised Structure of Onychine
Junko Koyama, Teruyo Sugita, Yukio Suzuta, and Hiroshi Irie*
*Faculty of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan
Abstract
Synthesis of an alkaloid, onychine and related compounds by application of a new method for constructing pyridine ring was described and the synthesis revealed that the structure of the alkaloid should be revised to 4-aza-1-methyl-fluoren-9-one from 1-aza-4-methyl-fluoren-9-one.
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■ Intramolecular Ring Formation of Phenyl Azide and Furan
Kenichi Yakushijin, Toyohisa Tsuruta, and Hiroshi Furukawa*
*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan
Abstract
Thermal and photochemical reaction of o-azidophenylethylfurans (1a-c) gave pyrrolo[1,2-a]quinolines (2, 3a-c and 6a,b) along with the usual nitrene products.
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■ Cyclic Tautomers of Tryptophans and Tryptamines II. Synthesis of 5-Nitro-, 5-Methoxy-, and 6-Methoxy-tryptophan Derivatives
Tohru Hino,* Mikiko Taniguchi, Akinori Gonsho, and Masako Nakagawa
*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Abstract
Nitration of the cyclic tautomer (2b) of Nb-methoxycarbonyl-DL-tryptophan methyl ester with fuming nitric acid followed by treatment with sulfuric acid in methanol gave 5-nitro-Nb-methoxycarbonyl-DL-tryptophan methyl ester (5) in excellent yield. The reaction of 2b with lead tetraacetate in trifluoroacetic acid followed by methylation provided 6-methoxy- (major) and 5-methoxy- (minor) derivatives (7 and 8) which were readily converted to 6- and 5-methoxytryptophan derivatives (10 and 11).
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■ Studies on Heterocyclic Analogues of Azulene. Part 5. Rearrangement of 7H-6a-Azacyclobuta[j]cyclopent[1,2,3-cd]azulene Ring System on Silica Gel
Noritaka Abe* and Tarozaemon Nishiwaki
*Department of Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan
Abstract
Rearrangement of 7H-6a-azacyclobuta[j]cyclopent[1,2,3-cd]azulene ring system to 3H-2a-azacyclopenta[ef]heptalene ring system by contact with silica gel was reported.
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■ Antimicrobial Agents from Higher Plants. A New Rotenoid, 11-Hydroxytephrosin, from Amorpha fruticosa
Lester A. Mitscher,* Ali Al-Shamma, Thomas Haas, Paul B. Hudson, and Young Han Park
*Department of Medicinal Chemistry, University of Kansas, 4070 Malott Hall, Lawrence, Kansas 66045-2506, U.S.A.
Abstract
The isolation, structure determination and bioactivity of 11-hydroxytephrosin (1) from Amorpha fruticosa is reported.
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■ Integriamide
Hisashi Ishii,* Ih-Sheng Chen, Tsutomu Ishikawa, Munekazu Ishikawa, and Sheng-Teh Lu
*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
Abstract
The structure of integriamide was established by preparing it due to the Baeyer-Villiger like oxidation of an immonium group of avicine.
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■ Acid-catalyzed Transformations in 1,3-Dioxacyclanes in Liquid Phase
Dilyus Lutfullich Rakhmankulov,* Evgeny Abramovich Kantor, and Robert Avetisovich Karakhanov
*Ufa Oil Institute, Kosmonavtov Str., 1, Ufa, 450062, Russia
Abstract
Data about 1,3-dioxacyclane reactions with water, alcohols, thiols, H2S, esters, amines, phenols are given. For the first time results obtained from reactions of reacetalization, exchange and recyclization of 1,3-dioxacyclanes have been summerized. Reactions mechanisms and kinetics have been investigated.
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■ Synthesis of Heterocycles Using Heterocumulenes Conjugated with the Carbonyl Group
Otohiko Tsuge*
*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan
Abstract
This review covers the contributions to the synthesis of heterocycles using heterocumulenes such as acyl and thioacyl isocyanates, and α-ketosulfenes which have been reported in recent years.