Regular Issue

Vol. 20, No. 6, 1983

28 data found. 1 - 28 listed
Communication | Regular issue | Vol 20, No. 6, 1983, pp. 981 - 982
Published online:
DOI: 10.3987/R-1983-06-0981
An Anomalous Dealkylation-Acylation of N,N-Dialkylanilines

George R. Newkome and Xia Yuanjiao

*Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803-1804, U.S.A.


N,N-Dialkylaniline undergoes a thermal N-dealkylation and acylation in the presence of 2-acetoxypyridines.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 983 - 984
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DOI: 10.3987/R-1983-06-0983
Heterocycles in Organic Synthesis. Part V. A Synthesis of 2,5-Diaryl-1,4-dithiins

Harjit Singh, Sunil K. Aggarwal, and Nageshwar Malhotra

*Department of Chemistry, Guru Nanak Dev University, Amritsar -143 005, Punjab, India


ω-(2-Methyl-4-quinazolinylthio or 2,6-dimethyl-4-pyrimidinylthio or 4-oxo-2-quinazolinylthio)acetophenones on treatment with hydrochloric or perchloric acid provide 2,5-diaryl-1,4-dithiins.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 985 - 990
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DOI: 10.3987/R-1983-06-0985
5-Acetoxy-2-pyrrolidinone as a Precursor for N-Acylimminium Ion

Tatsuo Nagasaka, Masako Abe, Naganori Ozawa, Yoshiyuki Kosugi, and Fumiko Hamaguchi

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Synthesis of 5-acetoxy-2-pyrrolidinone (3) and its reactions via N-acylimminium ion (6) with nucleophiles are described, especially in comparison with 5-alkoxy-2-pyrrolidinone (1) and 3-pyrrolin-2-one (4).

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 991 - 994
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DOI: 10.3987/R-1983-06-0991
Studies on Pyrimidine Derivatives. XXXI. Synthesis of Chloromethylpyrimidines by Reactin of Monomethylpyrimidine N-Oxides with Phosphoryl Chloride

Takao Sakamoto, Sohichi Kaneda, Yoshiaki Hama, Hiroshi Yoshizawa, and Hiroshi Yamanaka

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The reaction of 2- and 6-methylpyrimidine 1-oxides with phosphoryl chloride underwent the selective side-chain chlorination to give 2- and 6-chloromethylpyrimidines as sole products. No by-products such as 2-chloro- and 4-chloropyrimidines were obtained even in the cases of the N-oxides having a free active position in the nucleus.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 995 - 1000
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DOI: 10.3987/R-1983-06-0995
Pyrazole N- and C-β-D-Ribofuranosyl Nucleosides. Synthesis of Some β-D-Ribofuranosyl-4,7-methanoindazoles and Pyrazolo[1,5-a]azepines

Shin-ichi Nagai, Taisei Ueda, Noriichi Oda, and Jinsaku Sakakibara

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


Condensation of O-isopropylidene-D-ribosylhydrazine (1) with (1R,4S)-3-hydroxymethylenebornan-2-ones (2a-b) led to selective N-1 ribosylation of pyrazole ring to provide (4S,7R)-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-4,5,6,7-tetrahydro-4,7-methano-1H-indazoles (3a-b), and deprotected 4,7-methano-1H-indazole (4) after treatment with methanolic HCl. Structure determination including anomeric configuration assignment was discussed based on 1H-NMR spectroscopy. 1,3-Dipolar cycloaddition of diazoketone (5) with β-D-ribofuranosylpropiolate (8) followed by [1,5]sigmatropic rearrangement was used as a key reaction step in a novel synthesis of pyrazole C-ribofuranoside, (4S,7R)-3-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-oxo-4,7-methano-8H-pyrazolo[1,5-a]azepine (11). The protective groups of 11 were easily removed by methanolic HCl to give 3-(β-D-ribofuranosyl)-8H-pyrazolo[1,5-a]azepine (12).

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1001 - 1004
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DOI: 10.3987/R-1983-06-1001
Studies Related to β-Lactam Antibiotics. Part 8. A Facile Acid-catalyzed Ring Transformation of 1-Dethia-1-oxa-5-epiisoanhydropenicillins into Oxazolinones

Magoichi Sako, Kazuki Akira, Kosaku Hirota, and Yoshifumi Maki

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


1-Dethia-1-oxa-5-epiisoanhydropenicillin (2) undergoes with ease an acid-catalyzed ring transformation by virtue of the participation of an acylamino side chain to give oxazolinone derivative (4), as a mixture of geometrical isomers, under mild conditions in an excellent yield.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1005 - 1008
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DOI: 10.3987/R-1983-06-1005
A Synthesis of (±)-Phoracantholide M

Masazumi Ikeda, Kazunori Ohno, Masami Takahashi, Ko-ichi Homma, Takamasa Uchino, and Yasumitsu Tamura

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyoto 607-8414, Japan


(±)-Phoracantholide M was synthesized by a route involving an intramolecular photo[2+2]cycloaddition of 3-(5-hexenyl-2-oxy)-2-cyclohexen-1-one.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1009 - 1012
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DOI: 10.3987/R-1983-06-1009
1,3-Dipolar Cycloaddition of Pyridinium and Diazinium Dicyanomethylids with Bis(trimethylsilyl)acetylene: Synthesis of Trimethylsilyl Substituted Indolizines and Bis(trimethylsilyl)acetylene as an Acetylene Equivalent in 1,3-Dipolar Cycloaddition

Yukio Ikemi, Kiyoshi Matsumoto, and Takane Uchida

*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan


Cycloaddition reactions of pyridinium and diazinium dicyanomethylids with bis(trimethylsilyl)acetylene give either the corresponding 1,2-di(trimethylsilyl)-3-cyanoindolizines or the mixtures of these and 1-(trimethylsilyl)-3-cyanoindolizines depending on the substituents and the presence of another nitrogen in the pyridine ring. The trimethylsilyl group was smoothly removed under the catalytic influence of (n-Bu)4NF.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1013 - 1016
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DOI: 10.3987/R-1983-06-1013
Formation of 2-Alkylthio-substituted 2H-Pyrans in the Reaction of Cyclic 1,3-Diketones with Alkylthiodiphenylcyclopropenium Ions

Hiroshi Yoshida, Mikito Nakajima, Tsuyoshi Ogata, and Kiyoshi Matsumoto

*Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan


The reaction of methylthio-, ethylthio-, and benzylthiodiphenylcyclopropenium salts with 5- and 6-membered cyclic 1,3-diketones giving 2-alkylthio-2H-pyrans in good yields is reported.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1017 - 1020
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DOI: 10.3987/R-1983-06-1017
Reactions of o-Quinoid Compounds with Quadricyclanes IV. Cycloadditions of Tetrachloro-o-benzoquinone with Quadricyclanone

Willy Friedrichsen and Eggert Büldt

*Institut für Organische Chemie, Universität Kiel, Olshausenstrasse. 40, D-24098 Kiel, Germany


Quadricyclanone (1) reacts with tetrachloro-o-benzoquinone (2) to give both [σ2+ σ2+π4] (3, 4) and [σ2+σ2+π2] (5, 6, 7) cycloadducts.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1021 - 1025
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DOI: 10.3987/R-1983-06-1021
Synthesis of Fused Azoles: Synthesis of Several New Pyrrolo[2,3:4’,5’]pyrrolo[2,1-b]thiazoles and thiazolo[2,3-a]pyridine Derivatives

Fathy A. Khalifa, Bahia Y. Riad, and Fathia H. Hafez

*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt


The reactions of the 2-functionally substituted methylthiazol-4-one derivatives (1a-c) with N-arylmaleimides (2a, b) and ethyl acrylate have resulted in the synthesis of several new pyrrolo[2,3:4’,5’]lpyrrolo[2,1-b]thiazoles and thiazolo[2,3-a]pyridine derivatives. The structures of the synthesised compounds were assigned based on analytical and spectral data.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1027 - 1030
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DOI: 10.3987/R-1983-06-1027
Fluorescene and Phosphorescene Spectra of Firefly and Cypridina Oxyluciferins: A Question for the Multiplicity of the Excited States Produced in the Bioluminescent Systems

Nobutaka Suzuki, Takeshi Ueyama, Yasuji Izawa, Yoshiaki Toya, and Toshio Goto

*Faculty of Engineering, Mie University, 1515 Uehama-cho, Tsu, Mie 514-5807, Japan


Firefly oxyluciferin (1), the emitter of firefly bio- and chemiluminescence, gives identical FL and PL spectra under a certain condition. Hence, we showed that it would be necessary to examine the fluorescence and phosphorescence spectra before the identification of the multiplicity of the emitting species in the every bio- and chemiluminescence.

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Communication | Regular issue | Vol 20, No. 6, 1983, pp. 1031 - 1034
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DOI: 10.3987/R-1983-06-1031
One-pot Regioselective Synthesis of Naphtho[2,1-g]quinoline-7,12-dione Derivatives

Kazuhiro Maruyama, Seiji Tai, and Tetsuo Otsuki

*Department of Chemistry, Faculty of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan


Substituted naphtho[2,1-g]quinoline-7,12-diones were synthesized regioselectively by one-pot photochemical reaction of 6-bromo-7-methoxy-5,8-quinolinedione with 1,1-diarylethylene.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1035 - 1042
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DOI: 10.3987/R-1983-06-1035
The Differentital Reactivity of 5- and 3-Methyl Groups in the Reaction of 4-Substituted 2,3,5-Trimethylisoxazolium Salts with Aromatic Aldehydes

Angel Alberola, Ana M. González Nogal, and Francisco J. Pulido

*Deparamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid, Spain


2,3,5-Trimethylisoxazolium salts with electron-withdrawing groups at C-4 react with aromatic aldehydes to give 3- and/ or 5-arylidene derivatives resulting from the condensation at CH3 and/or CH3-5. The differential reactivity of 3- and 5-methyl groups is markedly influenced by the nature of the substituent at C-4 and varies in the same order as its kinetic acidity which was estimated from studies on deuteriodeprotonation. The influence of inductive, resonance and steric effects due to the 4-substituents on the course of the reaction is shown.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1043 - 1048
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DOI: 10.3987/R-1983-06-1043
Halogeno-1,2,5-thiadiazolopyridines and 1,2,5-Selenadiazolopyridines

Antoni Thomas and Wanda Sliwa

*Department of Organic Chemistry, Pedagogical University, Al. Armii Krajowej 13/15, 42-201 Czestochowa, Poland


Chloro- and bromo-1,2,5-thiadiazolopyridines and 1,2,5-selenadiazolopyridines have been synthesized by condensation of appropriate diamines with thionyl chloride or selenious acid.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1049 - 1054
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DOI: 10.3987/R-1983-06-1049
Some Reactions of 3-Bromo-4-bromomethyl-7-methoxycoumarin and 3-Bromo-4-methyl-7-methoxycoumarin with Refluxing N,N-Diethylaniline

Vernon G. S. Box and Clement G. Humes

*Department of Chemistry, Mona Campus, University of the West Indies, Mona, Kingston 7, Jamaica


N,N-diethylaniline effectively debrominated 3-bromo-4-methyl-7-methoxycoumarin and 3-bromo-4-bromomethyl-7-methoxycoumarin, at reflux. This and other reactions of the above-mentioned coumarins in refluxing N,N-diethylaniline provided supporting evidence for the mechanism of the fragmentation of simple 4-aryloxy-2-bromobut-2-enoates which occurred during their attempted Claisen rearrangement in refluxing N,N-diethylaniline.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1055 - 1061
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DOI: 10.3987/R-1983-06-1055
Cycloadditions with Capto-Dative Olefins, III. Addition of 2-Morpholino-Acrylonitrile to Various Aldonitrones

Dietrich Döpp and Jutta Walter

*Fachgebirt Organische Chemie, Universität Duisburg, Postfach 101629, D-4100 Duisburg 1, Germany


With very high regioselectivity, 2-morpholino-acrylonitrile (1) is added to aldonitrones to form unstable 5-morpholino-isoxazolidine-5-carbonitriles; the latter generally tend to form α,β-unsaturated carboxylic acid morpholides with ring opening and elimination of hydrogen cyanide.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1063 - 1066
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DOI: 10.3987/R-1983-06-1063
The Minor Alkaloids of Monnieria trifolia L.

J. Bhattacharyya and Leila M. Serur

*Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraiba, 58051-970 João Pessoa, PB, Brazil


Evolatine and 6-methoxy-7-hydroxydictamnine, alleged to have been isolated from the leaves of Monnieria trifolia L., appear to be identical to montrifoline and delbine respectively, the new alkaloids reported from the same source.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1067 - 1070
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DOI: 10.3987/R-1983-06-1067
Reactions of Creatone (2-Methylamino-1H-imidazole-4,5-dione)

Hiroshi Yamamoto, Toshihiro Takahashi, and Saburo Inokawa

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


Creatone (3) reversibly gives (3-methylguanidino)glyoxylic acid (6) and its ethyl ester (7) on heating with water and ethanol, respectively. These ring-opened compounds are important intermediates during the formation of creatone from creatine (1) and various other starting materials.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1071 - 1076
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DOI: 10.3987/R-1983-06-1071
Constituents of the Chinese Crude Drug “Sang-Bai-Pi” (Morus Root Barks) IV. Structures of Four New Flavonoids, Sanggenon H, I, J and K

Yoshio Hano and Taro Nomura

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Two new isoprene substituted flavanone derivatives, named sanggenon H and I, and two new isoprene substituted flavone derivatives, named sanggenon J and K, were isolated from the benzene extract of the Chinese crude drug “Sang-Bai-Pi” (Japanese name “Sohakuhi”), the root barks of Morus sp. (Moraceae). The structures I, II, III, and IV were proposed for these compounds on the basis of the spectroscopic evidence, respectively. Photooxidative cyclization did not occur with sanggenon K (IV) but with sanggenon J (III).

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1077 - 1081
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DOI: 10.3987/R-1983-06-1077
A Short and Efficient Synthesis of C-Nor-dihydrocodeinone — The Antipode of Goto’s Sinomenilone

Michael Bös, Wilhelm Fleischhacker, and Peter Tschany

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 10, A-1090 Vienna, Austria


In a four step synthesis, when using dihydrocodeinone, the C-nor-derivative 2 will be obtained in good yields. The reduction of the ringsize is achieved by bromination to the 1,7,7-tribromoketone 4 and heating it in an alkaline solution. Decarbonylation of the α-hydroxy acid 5 and subsequent catalytic hydrogenation of 6 lead to the desired enantiomer of Goto’s sinomenilone.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1083 - 1088
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DOI: 10.3987/R-1983-06-1083
Nitrogen Bridgehead Compounds Part 39. Synthesis and Reactions of 3-Phenoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-ones

Mária Balogh, István Hermecz, Ildikó Szilágyi, and Zoltán Mészáros

*CHINOIN Pharmaceutical and Chemical Works Ltd., P. O. Box 110, H-1325 Budapest, Hungary


3-Phenoxy- and 3-chloro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-ones (2) and (5) were prepared by the reactions of 2-aminopyridines and 2-phenoxy- or 2-chloroacetoacetate (4) and (7) in a mixture of phosphoryl chloride — polyphosphoric acid. The ring-transformation reactions of the pyridopyrimidines (2b) and (5b), and hydrogenation and nitration of the phenoxy derivatives (2) were also studied.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1089 - 1097
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DOI: 10.3987/R-1983-06-1089
S-Phenscylation of 6-Methyl-4-oxo-2-thio-2,3-dihydro-4H-1,3-oxazine and the Ring Transformation of the S-Phenacylated Compound

Tadashi Sasaki, Eikoh Ito, and Koji Asai

*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


1,3-Oxazine 1 reacted with phenacyl bromide in water using sodium hydroxide as a base to give S-phenacylated derivative 2, but the homogeneous conditions such as NaH in THF or NaOMe in methanol caused the base-induced cycloreversion of 1, resulting in the formation of thiocyanate 3. For the purpose of the intramolecular transformation to pyrimidine-fused heterocycle 11, 2 was treated with ammonia in refluxing ethanol, but gave amidamine 6 while 8 was obtained with ammonium acetate in refluxing acetic acid. Although the direct ring closure failed, the target 11 was finally synthesized by the cyclodehydration of ketamide 7 with phosphorus pentoxide at 250 °C.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1099 - 1107
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DOI: 10.3987/R-1983-06-1099
Synthesis of 5-Oxoindolizine Derivatives. II: Reaction of Ethyl Pyrrolidin-2-ylideneacetate (an Enamine Ester) with Acyclic α,β-Unsaturated Carbonyl Compounds

Tatsuo Nagasaka, Hitoshi Inoue, and Fumiko Hamaguchi

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Synthesis of some 5-oxoindolizine derivatives using ethyl pyrrolidin-2-ylideneacetate (1) and acyclic α,β-unsaturated carbonyl compounds is described. The structures of Michael adducts, intermediates for 5-oxoindolizines, obtained by treatment of with 1 dimethyl acetylenedicarboxylate or methyl propiolate are discussed.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1109 - 1116
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DOI: 10.3987/R-1983-06-1109
Heterocage Compound [IV]. Synthesis of Dioxacage Tricyclic Systems: Dioxabrendane and Dioxaisotwistane Skeleton with an Amino Function

Shun Inokuma, Akihiko Sugie, Koichi Moriguchi, and Junki Katsube

*Sumitomo Pharmaceuticals Research Center, 1-98, Kasugadenaka 3-chome, Konohana-ku, Osaka 554-0022, Japan


A series of dioxacage tricyclic systems with an amino function was synthesized in order to examine their chemical, physicochemical and biological properties.

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1117 - 1122
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DOI: 10.3987/R-1983-06-1117
Reactions of 3-Methyl-8H-cyclohept[d]isoxazol-8-one with 1,2-Alkanediamines

Yasunori Sudoh and Kimiaki Imafuku

*Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan


3-Methyl-8H-cyclohept[d]isoxazol-8-one (1) reacted with 1,2-ethanediamine to afford 3-methyl-5,6-dihydroisoxazolo[4,5-a]pyrazino[2,3-c]cycloheptene (2a) and 6-acetyl-1,2,3,4-tetrahydro-5H-cyclohepta[b]pyrazin-5-one (3a). The reaction with 1,2-propanediamine also gave two mixtures of methyl-substituted compounds [(2b and 2c) and (3b and 3c)]. The mixture of 3b and 3c was dehydrogenated to afford a mixture of 6-acetyl-2-methyl- and 6-acetyl-3-methyl-5H-cyclohepta[b]pyrazin-5-one (4b and 4c).

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Report | Regular issue | Vol 20, No. 6, 1983, pp. 1123 - 1126
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DOI: 10.3987/R-1983-06-1123
A New Versatile Synthesis of 4-Acyl-5-methyl-4-isoxazolin-3-ones

Soji Sugai, Kazuo Sato, Takashi Ueda, Kumiko Kataoka, and Kazuo Tomita

*Agroscience Research Laboratories, Sankyo Co., Ltd., 1041 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342, Japan


Treatment of N-substituted N-hydroxyacetoacetamides 1 with acyl chlorides in the presence of two equivalents of triethylamine gave 4-acyl-5-methyl-4-isoxazolin-3-ones 5. The reaction was thought to proceed via acyl rearrangement as shown in 8 and 9.

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Review | Regular issue | Vol 20, No. 6, 1983, pp. 1127 - 1171
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DOI: 10.3987/R-1983-06-1127
Cycloaddition, Ring-opening, and Other Novel Reactions of Thiophenes

Brian Iddon

*Department of Chemistry and Applied Chemistry, The Ramage Laboratories, University of Salford, Salford M5 4WT, U.K.


Synthetically useful reactions of thiophenes and benzo[b]thiophenes are reviewed in which the aromaticity of the thiophene ring is lost either permanently or temporarily, i.e. so-called “non-benzenoid” reactions. These include cycloadition reactions with arynes, hetarynes, carbenes, nitrenes, olefins, acetylenes, ketones, and other substrates and various ring-opening reactions, e.g. of organometallic derivatives and 2-aminothiophenes. Also reviewed are C-2 protonation and reactions of thiophenes at the sulphur atom, e.g. alkylation. Brief reference is made to thiophene l,l-dioxides and attention is drawn to other little-used reactions of thiophenes of potential synthetic usefulness, e.g. inverted reactivity of thienyl-lithium compounds.

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28 data found. 1 - 28 listed