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. 16, No. 8, 1981
Published online:
■ Synthesis of Thieno[3,2-c]- and Thieno[2,3-c]pyrid-3-ones
Kyosuke Satake,* Toshiyuki Imai, Masaru Kimura, and Shiro Morosawa
*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan
Abstract
The Friedel-Crafts cyclization of N-(3-thenyl)- and N-(2-thenyl)-glycine derivatives is described. The method leads to an alternative synthesis of 1,2,3,4-tetrahydro-N-[(2-chlorophenyl)methyl]thieno[3,2-c]pyridine(ticlopidine)(6d).
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■ Alkaloids of Michelia fuscata Blume: The Structure and Synthesis of Magnolamine
Hitoshi Tanaka, Ayako Harada, Kazuhiko Ichino, and Kazuo Ito*
*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan
Abstract
The cleavage reaction of triethylmagnolamine (3) by sodium-liquid ammonia determined the location of phenolic functions in magnolamine (2). Furthermore, the synthesis of magnolamine was carried out by the Ullmann reaction of two optically active compounds (10) and (12). The synthetic product was completely identical with natural magnolamine by comparison of various spectra and t.l.c. behavior. Thus, it was clarified that the structure of magnolamine is indicated by the formula (2).
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■ A Novel Synthesis of 2-Substituted Quinazolin-4(3H)-ones
Jan Svetlík*
*Drug Research Institute, Palárikova 31, 811 04 Bratislava, Slovakia
Abstract
Aromatic or mixed carbodiimides and ketenimines react with ethyl allophanate to give corresponding substituted quinazolin-4(3H)-ones.
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■ High-pressure Diels-Alder Reactions of Furans with α-Chloro- and α-Acetoxyacrylonitrile
Hiyoshizo Kotsuki* and Hitoshi Nishizawa
*Department of Material Science, Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan
Abstract
The Diels-Alder reactions of furans with α-chloro- and α-acetoxyacrylonitrile very nicely proceeded under the conditions of 15 kbar and 30°C in dichloromethane. The adducts were proved to be a useful precursor for the synthesis of 7-oxa-bicyclo[2.2.1]heptanone derivatives.
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■ Chiral Route to Some Alkaloids through Asymmetric Iodolactonization
Seiichi Takano,* Chikara Murakata, Yoko Imamura, Nobuhiko Tamura, and Kunio Ogasawara
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Three chiral γ-lactone derivatives (1), (2), and (3), leading to chiral synthesis of three alkaloids, (-)-secopandoline (4), (-)-quebrachamine (5), and (+)-mesembrine (6), have been synthesized through the asymmetric iodolactonization of the amides (8) from the symmetric carboxylic acids (7) and the chiral amines.
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■ Synthesis of 5-Aryl-5,6,7,8-tetrahydrothiazolo[3,4-a]pyridinium Bromides
Takeshi Hara* and John C. Sheehan
*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, U.S.A.
Abstract
5,6,7,8-Tetrahydro-5-phenylthiazolo[3,4-a]pyridinium bromide (1a) and 5-(p-chlorophenyl)-5,6,7,8-tetrahydrothiazolo[3,4-a]pyridinium bromide (1b) have been synthesized with 4-(3-carboethoxypropyl)-thiazole (3) and/or 4-(4-phenyl-3-butenyl)thiazole (9a) or 4-[4-(p-chlorophenyl)-3-butenyl]thiazole (9b) as an intermediate.
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■ Makomakine and Mokonine, New Indole Alkaloids from Aristoteria serrata
I. Ralph C. Bick* and Mohammad A. Hai
*Department of Chemistry, University of Tasmania, GPO Box 252C Hobart, Tasmania, 7001, Australia
Abstract
A key intermediate, makomakine (I), involved in the proposed scheme of biosynthesis of the Aristotelia alkaloids, has been isolated from an A. serrata extract, together with makonine (II), a dehydroaristotelinone.
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■ A New Synthesis of Carbepenams through the Formation of the 1,5-Bond as a Final Step
Kapa Prasad,* Gerhard Schulz, Ching-Pong Mak, Helmut Hamberger, and Peter Stütz
*Sandoz Research Institute, A-1235 Vieena, Austria
Abstract
Synthetic methods for the preparation of the racemic carbapenems 12 and 13 and an oxapenam 16 starting from diazoketone 11 are described.
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■ Structure of Forsythoside A, a Antibacterial Principle of Forsythia suspensa Leaves
Katsuya Endo, Kazuhiro Takahashi, Toyoko Abe, and Hiroshi Hikino*
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
A new glycoside, forsythoside A, exhibiting antibacterial activity, has been isolated from Frosythia suspensa leaves. Degradative and spectroscopic studies have established the structure of forsythoside A as shown in formula I.
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■ Synthesis of 2-Formyladenosine Using Diethoxyacetonitrile as a Synthon
Teiichi Murakami, Masami Otsuka, Susumu Kobayashi, and Masaji Ohno*
*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan
Abstract
Diethoxyacetonitrile has been utilized for the effective synthesis of adenine derivatives as a synthon. Novel 2-formyladenine (2b) and 2-formyladenosine (5b) have been prepared in high yields starting from AICN (1) and AICNR (4b), respectively.
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■ Revised Structure of Isoterchebin, Isolated from Cornus officinalis
Takuo Okuda,* Tsutomu Hatano, and Tsutomu Yasui
*Faculty of Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan
Abstract
A dehydroellagitannin isolated from the fruit of Cornus officinalis, whose structure is assigned as 1,2,3-tri-O-galloyl-4,6-O-dehydrohexahydroxydiphenoyl-β-D-glucopyranose (I), is considered to be identical as isoterchebin which had been presumed to have structure (V).
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■ Dechlorination of Some Chloropyrazines and Their N-Oxides
Yasuo Akita and Akihiro Ohta*
*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
By heating with sodium formate and tetrakis(triphenylphosphine)palladium, chloropyrazines were converted to the parent pyrazines in satisfactory yields. The chlorine atoms of chloropyrazine N-oxides could also be removed, leaving the N-O group.
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■ Isolation and Characterization of a Substituted Benzpyridone from Darius Crude
Asha Masohan and Virendra Kumar Bhatia*
*Indian Institute of Petroleim, Dehradun, India
Abstract
Heavy ends of petroleum are becoming important contributors to future petroleum requirements. A knowledge of the composition of these materials is, therefore, necessary for their efficient processing and use. Isolation and characterisation of a substituted benzpyridone from 300-470°C fraction of Darius crude is presented.
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■ Novel and Convenient Syntheses of Substituted 1,4-Diazocines and 1,4-Diazonines
Geeta Singh and Kailash Nath Mehrotra*
*Chemistry Department, Faculty of Science, Banaras Hindu University, Varanasi-221 005, India
Abstract
Treatment of dianils with sodium in dry ether followed by addition of 1,4-dichlorobutane and 1,5-dichloropentane gave 1,2,3,4-tetraaryl-1,4,5,6,7,8-hexahydro-1,4-diazocines and 1,2,3,4-tetraaryl-4,5,6,7,8,9-hexahydro-1H-1,4-diazonines respectively.
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■ Bicyclic Peroxides from a 1,4-Diazepine
V. T. Ramakrishnan and Joseph H. Boyer*
*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.
Abstract
An adduct, 3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo[4.2.1]non-3-ene, was obtained from 2,3-dicyano-5,7-dimethyl-6H-1,4-diazepine and hydrogen peroxide in the presence of alkali or a tertiary amine. It was dehydrogenated by iodobenzene diacetate into 3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo[4.2.1]nona-2,4-diene; further oxidation by m-chloroperbenzoic acid gave 4,5-dicyano-1,8-dimethyl-2,7-diaza-3,6,9,10-tetraoxatetracyclo[6.2.1.02,405,7]undecane.
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■ The Reaction of 3-Hydroxycoumarin with Benzalacetone
V. K. Ahluwalia,* Keya Mukherjee, and Nimmi Rani
*Department of Chemistry, University of Delhi, Delhi-110 007, India
Abstract
The reaction of 3-hydroxycoumarin (I) with benzalacetone in presence of dioxane-piperidine afforded 3-hydroxy-4-(α-phenyl-β-acetylethyl )coumarin (IIa) which on acetylation with Ac2O/pyridine gave a cyclised product, 2-acetoxy-2-methyl-4-phenyl-10-oxo-3,4-dihydropyrano[2,3-c][1]benzopyran (III).
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■ Synthesis of Ellipticine: Review and Computer Suggestions
R. Barone* and M. Chanon
*Laboratoire de Chimie Inorganique, Faculté des Sciences et Techniques de St.-Jérôme, Université e’Aix-Marseille III, Rue H. Poincaré, 13397 Marseille Cedex 13, France
Abstract
A review of recent syntheses of ellipticine is presented and some suggestions of a computer assisted organic synthesis program are given.
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■ The Synthesis and Reactions of Heterocycles under High Pressures
Kiyoshi Matsumoto,* Takane Uchida, and R. Morrin Acheson
*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan
Abstract
In this review are brought together the representative results which are presently available concerning the use of high pressures on reactions involving heterocyclic compounds.