Regular Issue

Vol. 22, No. 5, 1984

46 data found. 31 - 46 listedFirst Previous
Report | Regular issue | Vol 22, No. 5, 1984, pp. 1137 - 1142
Published online:
DOI: 10.3987/R-1984-05-1137
2,3,8-Triazabicyclo[3.3.1]non-3-ene. A New Heterocyclic System

Joan Bosch,* Mario Rubiralta, Natividad Valls, and Anna Diez

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain


The formation of 2,3,8 -triazabicyclo[3.3.1]non-3-ene system by reaction of 4-acyl-1,2,3,4-tetrahydropyridines with hydrazine is described.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1143 - 1146
Published online:
DOI: 10.3987/R-1984-05-1143
Synthesis of 7-Substituted 4H-1,4-Benzothiazines

Radha Raman Gupta,* Rakesh Kumar Gautam, and Rakesh Kumar

*Department of Chemistry, University of Rajasthan, Jaipur 302 004, India


One step synthesis is reported for 7-substituted 4H-1,4-benzothiazines involving the condensation of 5-substituted 2-aminobenzenethiols with p-methoxy and p-methylbenzoylacetone in DMSO which causes oxidative cyclisation.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1147 - 1153
Published online:
DOI: 10.3987/R-1984-05-1147
Heterocycles. XIV. Efficient Stereocontrolled Synthesis of Racemic Flavonoids

Hiroshi Takahashi, Yumiko Kubota, Hiroko Miyazaki, and Masayuki Onda*

*School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan


Stereocontrolled synthesis of the flavonoids (2, 4 and 5) is described. Racemlc taxiolin (dihydroquercetin) (14) is synthesized by application of this method.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1155 - 1159
Published online:
DOI: 10.3987/R-1984-05-1155
A Novel Preparation of the 1,3-Benzoxazepine Ring System

Alan R. Katritzky,* Olga Rubio, Radi Awartani, Nazih Latif, Nawal Mishriky, and Fahmy M. Assad

*Center for Drug Discovery, College of Pharmacy, University of Florida, Gainesville, Florida 32611-7200, U.S.A.


Novel 1,3-benzoxazepines (5) are obtained by a new ring expansion rearrangement of benzinones (1).

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1161 - 1167
Published online:
DOI: 10.3987/R-1984-05-1161
Unsaturated β-Lactams

Marion Thielmann and Ekkehard Winterfeldt*

*Institut fur Organische Chemie, Universität Hannover, Schneiderberg 1 B, D-30167 Hannover, Germany


Lithium enolates of β-lactams are shown to exclusively yield 1,2-addition products to propargylic aldehyde. Products of subsequent Peterson elimination and propargylic rearrangements are described.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1169 - 1173
Published online:
DOI: 10.3987/R-1984-05-1169
Studies on Phenothiazines. Part 10: Synthesis of 1-Ethoxy-7-substituted Phenothiazines

Radha Raman Gupta* and Rakesh Kumar

*Department of Chemistry, University of Rajasthan, Jaipur 302 004, India


Synthesis of 1-ethoxy-7-substituted phenothiazines via Smiles rearrangement is reported. 2-Amino-3-ethoxybenzenethiol was condensed with halonitrobenzenes and the substituted diphenylsulphides, so obtained, were converted into substituted formyl derivatives by formic acid. The latter on treatment with alcoholic KOH underwent Smiles rearrangement and yield 1-ethoxy-7-substituted phenothiazines. The structure of the synthesized compounds have been confirmed by their elemental analysis and spectral studies.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1175 - 1178
Published online:
DOI: 10.3987/R-1984-05-1175
Ring Bromination in the Attempted Nitration of 2,5-Dibromo-3-dibromomethylthiophen

John D. Coyle,* Edmund J. Haws, Olufemi Oduntan, and John T. Rogers

*Chemistry Department, The Open University, Milton Keynes MK7 6AA, U.K.


Treatment of 2,5-dibromo-3-dibromomethylthiophen with mixed nitric and sulphuric acids or with fuming (>96%) nitric acid gives 2,4,5-tribromothiophen-3-carbaldehyde after aqueous work-up.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1179 - 1187
Published online:
DOI: 10.3987/R-1984-05-1179
Pseudoesters and Derivatives. XXI. The Reaction of 4-Bromo-5-methoxy-3-pyrrolin-2-one with Nucleophiles

M. Angeles Jiménez, M. Carmen Ortega, Amelia Tito, and Francisco Fariña*

*Instituto de Quimica Organica General, Consejo Superior Investigaciones Cientificas, Calle Juan de la Cierva, 3, E-28006 Madrid, Spain


Nucleophilic substitution of the halogen in 4-bromo-5-methoxy-3-pyrrolin-2-one (1) is observed by using dimethylamine, azide, phenylmethanethiolate and 2-propanethiolate ions. The reaction of 1 with methoxide ion affords 5,5-dimethoxy-3-pyrrolin-2-one (2). As a general rule, secondary amines react with 1 yielding the respective 4,5-diaminosubstituted 5-pyrrolin-2-one (5). Although the initial reaction of 1 with thiolate ions is the halogen substitution, further reaction with thiolate affords the respective 3-(alkylthio)pyrrolidine-2,5-dione (8) .

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1189 - 1193
Published online:
DOI: 10.3987/R-1984-05-1189
A Facile Synthesis of Novel Heterocycle-conjugated Quinoxalines

Yoshihisa Kurasawa,* Shoko Nakamura, Kayano Moriyama, Kumi Suzuki, and Atsushi Takada

*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan


Novel pyrazole- and 1,3,4-oxadiazole-conjugated quinoxalines (5-9) were synthesized selectively from 3-hydrazinocarbonylmethylene-2-oxo-1,2,3,4-tetrahydoquinoxaline (1).

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1195 - 1210
Published online:
DOI: 10.3987/R-1984-05-1195
Iodination of Some Diazines and Diazine N-Oxides

Misa V. Jovanovic*

*Department of Chemistry, Southern Methodist University, P.O. Box 750314, Dallas, TX 75275-0314, U.S.A.


A number of monosubstituted pyrazines, pyrimidines, and their N-oxides having the electron-donating amino groups were successfully iodinated. Depending on the reaction conditions, the 3-substituted pyrazine 1-oxides having a bulky dialkylamino group yielded the 6-iodo and 2,6-diiodopyrazine N-oxide derivatives together with some deoxygenated products. The mechanism with supportive evidence was presented to account for these chemical transformations.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1211 - 1216
Published online:
DOI: 10.3987/R-1984-05-1211
p-Toluensulfonic Acid and Cation Exchange Resin in Aprotic Solvent: Valuable Catalysts for Fischer Indolization

Yasuoki Murakami,* Yuusaku Yokoyama, Tomoko Miura, Hiroko Hirasawa, Yuuko Kamimura, and Miyoko Izaki

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


p-Toluenesulfonic acid and cation exchange resin (Amberlyst-15) in aprotic solvent were found to serve as a good catalyst for Fischer indolization in many cases. With this condition ethyl indole-2-carboxylate was prepared more conveniently in better yield than by previous methods.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1217 - 1224
Published online:
DOI: 10.3987/R-1984-05-1217
Formation of Anomalous Products in tne Leuckart Reaction of the 2-Bromo-4,5-dimethyoxybrnzyl 2-Hydroxy-3,4-dimethoxyphenyl Ketone

Esther Domínguez,* Esther Lete, M. Jesús Villa, and Carmen Iriondo

*Departamento de Física Aplicada, Facultad de Ciencias, Universidad del País Vasco, Apartado 450, 01080 Vitoria-Gasteiza, Spain


The Leuckart reaction of the 2-bromo-4,5-dimethoxybenzyl 2-hydroxy-3,4-dimethoxyphenyl ketone (2) afforded, not the expected amine, but three anomalous products: the stilbene (3), the isoflavone (4) and the pyrimidine (5). Their structures have been established on the basis of their spectral data.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1225 - 1230
Published online:
DOI: 10.3987/R-1984-05-1225
A Facile Route to Fused Heterocycles with an Exocyclic by Intramolecular Nucleophilic Aminations to Acetylene

Tadashi Sasaki* and Ikuo Shimizu

*Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


The novel method for synthesis of fused heterocycles with an exocyclic methylene was investigated. The terminally acetylene-substituted heterocycles 3a-c and 6a-d were converted to the fused heterocycles with an exocyclic methylene 4a-c and 7a-d by intramolecular nucleophilic amination to acetylene part.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1231 - 1234
Published online:
DOI: 10.3987/R-1984-05-1231
A Convenient Synthesis of Pyrimido[5,4-g]pteridinetetrones

Yoshihisa Okamoto,* Kuniyoshi Ogura, Yoshihisa Kurasawa, and Toshio Kinoshita

*Center for Natural Sciences, Kitasato University, 1-15-1, Kitasato, Sagamihara, Kanagawa 228-8555, Japan


The oxidation reactions of 5,6-diaminouracil derivatives with ferric chloride gave pyrimido[5,4-g]pteridinetetrones in good yield.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1235 - 1247
Published online:
DOI: 10.3987/R-1984-05-1235
Syntheses of 2-Alkyl-3-(4-dialkylaminoalkoxy-benzoyl)-thieno[3,2-c]pyridines

Daniel Fréhel,* Robert Boigegrain, and Jean-Pierre Maffrand

*Linge Hémobiologie, Sanofi Recherche, 195 route d’Espagne, 31036 Toulouse, France


This paper deals with the syntheses of thieno(3,2-c)pyridinic isosteres 4 of two potent anti-anginal and/or antiarrythmic agents : amiodarone 1 and butoprozin 2. The corresponding tetrahydrogenated analogs are also synthesized.

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Report | Regular issue | Vol 22, No. 5, 1984, pp. 1249 - 1252
Published online:
DOI: 10.3987/R-1984-05-1249
Further Studies on the Colorination Reaction of 7-Substituted Theophylline Derivativces

Tetsuji Kametani,* Setsu Saitou, and Toshio Honda

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


The colorination reaction of 7-substituted theophylline derivatives was described.

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46 data found. 31 - 46 listedFirst Previous