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. 23, No. 8, 1985
Published online:
■ Reaction of Pyridinium Bis(methoxycarbonyl)methylid with Diphenylcyclopropenethione: A Revised Structure for One of the Products
Kiyoshi Matsumoto,* Takane Uchida, Yoshiko Yagi, Hiroshi Tahara, and R. Morrin Acheson
*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan
Abstract
A structure for one product from the reaction of pyridinium bis(methoxycarbonyl)methylid and diphenylcyclopropanethione is revised to be 5,5-bis(methoxycarbonyl)-2,3,6,7-tetraphenyl-5H-thieno[2,3-e]thiopyrane.
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■ The Chemical Reactivitu of 2,2,3,3-Tetramethyl-1-aziridinecarboximidate
Sang-Hun Jung and Harold Kohn*
*Department of Chemistry, University of Houston, Houston, TX 77004, U.S.A.
Abstract
The activated aziridine, 2,2,3,3-tetramethyl-1-aziridinecarboximidate, does not rearrange to the corresponding 4,5-dihydro-4,4,5,5-tetramethyl-2-ethoxyimidazole in the presence of either nucleophilic catalysts or acids, rather the major products obtained were ring-opened adducts. The mechanism of these atypical transformations are discussed.
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■ Novel Fused-Ring Derivatives of 1,4-Benzodiazepine System: Synthesis of Tetrahydro-1H-triazolo[4,3-d][1,4]benzodiazepines
Giuseppe Capozzi, Alba Chimirri, Silvana Grasso, Giovanni Romeo,* and Giovanni Zappia
*Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, 98168 Messina, Italy
Abstract
A novel class of annelated 1,4-benzodiazepines is synthesized by 1,3-dipolar cycloaddition of suitable nitrilimines to the C=N bond of the benzodiazepine ring. Structures and conformations of adducts have been assigned by means of spectroscopic measurements. The additional heterocyclic nucleus has been found to influence dramatically the conformational mobility of the heptatomic ring.
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■ Reactions of Uracils 9. Synthesis and Reactions of 6-Substituted Benzylamino-5-(ethoxycarbonylethenyl)-1,3-dimethyluracils
Péter Mátyus,* László Löwinger, and Heinrich Wamhoff
*Institute for Drug Research Ltd., H-1325 Budapest, POB 82, Hungary
Abstract
Starting from 6-chloro-5-(2-ethoxycarbonylethenyl)-1,3-dimethyluracil the novel 6-substituted benzylamino derivatives 1c-f were synthesized which gave either 2,4,7-trioxopyrido[2,3-d]pyrimidines 2c-e or the 6-substituted benzylidenamino analogues 3c-f depending on the reaction conditions. A kinetic study was also carried out.
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■ Preparation and Thermal Properyies of 2-Aryl-5-benzoylthio-1,3,4-oxadiazoles
Yasuo Saegusa,* Norihiko Akano, Shigeo Nakamura, Nguyen Chau, and Yoshio Iwakura
*Faculty of Technology, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
Abstract
Novel type of thioesters, 2-aryl-S-benzoylthio-1,3,4-oxadiazoles (3a-3d), were prepared by the elaborate benzoylation of 2-aryl-1,3,4-oxadiazoline-5-thiones (1a-1d), and their thermal behavior was elucidated by differential thermal analysis (DTA).
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■ Synthesis of Novel 6-Substitutued 2-Chloro-3-methylquinoxalines
Kenji Makino,* Gozyo Sakata, and Katsushi Morimoto
*Central Research Institute, Nissan Chemical Industries Ltd., 722-1 Tsuboicho, Funabashi, Chiba 274-8507, Japan
Abstract
Facile synthesis of novel 6-substituted 2-chloro-3-methylquinoxalines (4a-d) is described. Intramolecular cyclization reaction of 4-substituted 2-nitroacetoacetanilides (1a-d) in basic conditions affordaed 6-substituted 2(1H)-quinoxalinone-4-oxides (2a-d) and in situ, which could be converted into novel 6-substituted 3-methyl-2(1H)-quinoxalinones (3a-d) using ethyl acetoacetate. 3a-d were chlorinated with phosphoryl chloride to afford 4a-d.
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■ Constituents of West African Medical Plants. XVIII. The Annoidines — A New Class of Prenylated Bisindole Alkaloids from Annonidium mannii
Hans Achenbach* and Christian Renner
*Institute of Pharmacy, Department of Pharmaceutical Chemistry, University of Erlangen, D-8520 Erlangen, Germany
Abstract
From the stem bark of Annonidium mannii annonidines A - E (3 - 7) have been isolated and their structures determined. 3 to 7 belong to a new structural type of prenylated bisindole alkaloids.
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■ Recent Progress in the Quinoline Chemistry: Utility of 3-Alkoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxalines as Starting Materials
Yoshihisa Kurasawa* and Atsushi Takada
*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan
Abstract
3-Alkoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxalines 1 have been converted into various quinoxaline derivatives via versatile intermediates by the facile synthetic methods. This review describes these synthetic routes, including the mechanistic considerations and the spectroscopic properties.