Regular Issue

Vol. 12, No. 10, 1979

17 data found. 1 - 17 listed
Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1269 - 1273
Published online:
DOI: 10.3987/R-1979-10-1269
Studies in the Dihydropyridine Series III. Piperideine Synthons by Nucleophilic Substitution to Dihydropyridinetricarbonyl Chromium (0) Complexes

James P. Kutney,* Masaki Noda, and Brian R. Worth

*Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, B.C. V6T 1Z1, Canada


Overall nucleophilic substitution of N-methyl-3-ethyl-1,2-dihydropyridinetricarbonylchromium (0) complex afforded the corresponding 2,5-disubstituted, complexed, unit. Oxidative work-up conditions provided the parent heterocycles. In a similar fashion, N-methyl-3-ethyl-1,6-dihydropyridinetricarbonylchromium (0) provided 3,5-disubstituted products.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1275 - 1279
Published online:
DOI: 10.3987/R-1979-10-1275
Configurational and Chemical Studies on (—)-6,8-Dibromobornane-2-one

Shin-ichi Nagai, Noriichi Oda, and Isoo Ito*

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


The absolute configuration of C6-bromine in (-)-6,8-dibromobornane-2-one (2) was confirmed by the spectral data. Condensation of 2 with hydrazine hydrate gave diazatricyclo[4,4,0,05,9]dec-7-one (7) which provided Diels-Alder adducts (9a,b) with dienes.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1281 - 1284
Published online:
DOI: 10.3987/R-1979-10-1281
2-(2-Iminoacetic Acid)-3-(2H)-benzofuranone: A New Metabolite from Shorea robusta Seeds

Devendra Kumar*

*Polymers and Special Chemical Division, Vikram Sarabhai Space Centre, Trivandrum-695022, India


A new metabolite, 2-(2-Iminoacetic acid)-3-(2H)-Benzofuranone has been isolated from the ethyl acetate extract of the defatted SHOREA ROBUSTA seeds. Its structure has been established using spectroscopic methods and by synthesis of its dimethyl derivative.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1285 - 1288
Published online:
DOI: 10.3987/R-1979-10-1285
Reaction of N,N’-Carbonyldiimidazole and N,N’-Thionyldiimidazole with Amides: An Imidazole Transfer Reaction

Masaru Ogata,* Hiroshi Matsumoto, and Shiro Kida

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan


Reaction of N,N’-thionyldiimidazole with amides effects the formation of imidoylimidazoles in moderate yield under neutral conditions. The hydrogen bonding in o-hydroxybenzamides activates the amide group (carbonyl function) in its reaction with N,N’-carbonyldiimidazole.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1289 - 1295
Published online:
DOI: 10.3987/R-1979-10-1289
On the Structures of Mulberrin, Mulberrochromene, Cyclomulberrin, and Cyclomulberrochromene

Taro Nomura* and Toshio Fukai

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


Direct comparison of mulberrin with kuwanon C, and mulberrochromene with morusin were carried out. Mulberrin and mulberrochromene were proved to be identical with kuwanon C and morusin, respectively. The linear structures of mulberrin and mulberrochromene as well as cyclomulberrin and cyclomulberrochromene should be reversed to the angular structures, I, II, III, and IV, respectively.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1297 - 1299
Published online:
DOI: 10.3987/R-1979-10-1297
Synthesis of 3-Hydroxy-5-methylisoxazole and 5-Substituted 4-Oxazolin-2-one

Hiroshi Fukumi,* Kazuhiko Oohata, and Kazuo Takada

*Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan


An improved synthesis of 3-hydroxy-5-methylisoxazole and some rearrangements of O-benzoyl β-keto-propionohydroxamates with the formation of 5-substituted 4-oxazolin-2-one are described.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1301 - 1303
Published online:
DOI: 10.3987/R-1979-10-1301
A Formal Total Synthesis of Thienamycin

Tetsuji Kametani,* Shyh-Pyng Huang, Yukio Suzuki, Shuichi Yokohama, and Masataka Ihara

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


Careful hydrolysis of the amino alcohol (3), obtained from trans-4-methoxycarbonyl-3-(2’,2’-dimethoxyethyl)-5-methylisoxazoline (2), followed by treatment with dicyclohexylcarbodiimide gave two trans-azetidinones (4 and its epimer) together with the cis-isomer (5). Reaction of 3 with methylmagnesium iodide yielded the trans-azetidinone (4) along with the cis-one (5). The trans-azetidinone (4) was converted into the alcohol (7) and the thioacetal (8), which had been correlated to thienamycin (1).

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1305 - 1310
Published online:
DOI: 10.3987/R-1979-10-1305
Enantioselective Thiolysis of α-Amino Acid p-Nitrophenyl Ester Salts by Thiol-bearing Chiral Crown Ethers

Shigeki Sasaki and Kenji Koga*

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan


Studies have been made on the design, synthesis, and test of thiol-bearing chiral crown ethers that work enantioselectively in the thiolysis of α-amino acid ester salts. It is shown that crown ethers (3 and 4), prepared from (+)-(1R,2R,3S,4S)-camphane-2,3-diol (12) and (-)-(1R,2S,3R,4S)-camphane-2,3-diol (16) respectively, exhibit enantiomeric discrimination by a factor of 1.7-1.9 in the rates of p-nitrophenol release from alanine p-nitrophenyl ester salts.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1311 - 1313
Published online:
DOI: 10.3987/R-1979-10-1311
Cyclisation of γ-Phenylpropyl Isocyanate to 1H-2-Benzazepin-1-one: An Improved Synthesis of Alkaloid Elwesine

Tamaki Fushimi, Hironori Ikuta, Hiroshi Irie,* Kazuyuki Nakadachi, and Shojiro Uyeo

*Faculty of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan


Treatment of γ-(3,4-dimethoxyphenyl)propyl isocyanate with phosphorous oxychloride followed by stannic chloride gave 1H-7,8-dimethoxy-2-benzazepin-1-one in fair yield, providing a convenient method for constructing 1H-benzazepin-1-one derivatives. Application of the procedure on β-[4-acetoxy-1-(3,4-methylenedioxyphenyl)cyclohexyl]propionic acid furnished an improved synthesis of alkaloid elwesine (dihydocrinine) isolated from Amaryllidaceae plant.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1315 - 1318
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DOI: 10.3987/R-1979-10-1315
Syntheses of Some Dithioketene Acetal Azetidinone Derivatives

Masayuki Shibuya* and Seiju Kubota

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi 1, Tokushima 770-8505, Japan


Dithioketene acetal azetidinone derivatives (3)-(8) were prepared by the base induced reaction of 4-acetoxyazetidin-2-one (1) with β-hydroxydithiocinnamic ester and its analogues. The E and Z isomers of the products were separated and their configurations were determined in NOE experiments. Both isomers of compounds (3)-(7) showed moderate synergistical activity with penicillins against some resistant strains of bacteria.

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1319 - 1322
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DOI: 10.3987/R-1979-10-1319
Reaction of Thiobenzoyl Isocyanates with Trimethylsilyl Cyanide

Otohiko Tsuge* and Satoshi Urano

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


Thiobenzoyl isocyanates were found to react with trimethylsilyl cyanide to afford the corresponding 2-phenyl-5-thiobenzoyl-7-trimethylsilylimino-4,5,6,7-tetrahydro-1,3,5-thiadiazepine-4,6-diones (2:1 adducts).

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Communication | Regular issue | Vol 12, No. 10, 1979, pp. 1323 - 1326
Published online:
DOI: 10.3987/R-1979-10-1323
Synthesis and Metabolism of 5-Alkylpyrimidine-2-carboxylic Acids

Hiroshi Yamanaka,* Michinao Mizugaki, Mataichi Sagi, Kiyoto Edo, Hiroshi Miyazaki, Hideki Takayama, and Yukiko Minatoagwa

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


The metabolism of 5-propylpyrimidine-2-carboxylic acid, an azalogue of fusaric acid, has been investigated. The chain-elongated metabolites in the carboxyl group at the 2-position on the ring were identified in rat urine. The synthesis of the substrate and its main metabolite is also described.

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Report | Regular issue | Vol 12, No. 10, 1979, pp. 1327 - 1330
Published online:
DOI: 10.3987/R-1979-10-1327
Synthesis of Heterocycles via Lactones. Part III. A Synthesis of Berbines — Synthesis of (±)-Scoulerine and Pseudoepitetrahydroberberine

Ganesh D. Pandey and Kamla P. Tiwari*

*Department of Chemistry, University of Allahabad, Allahabad, 211002, India


The utilization of the bromo esters (I) and (VII) for the functionalization of the ring D can provide an interesting synthetic entry to the berbines.

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Report | Regular issue | Vol 12, No. 10, 1979, pp. 1331 - 1333
Published online:
DOI: 10.3987/R-1979-10-1331
Synthesis of 1,2,11,12-Tetrathia[2.2](2,7)naphthalenophane

Francesco Bottino* and Sebastiano Pappalardo

*Istituto Dipartimentale di Chimica, Chimica Industriale, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy


Mild oxidation of 2,7-dimercapto-naphthalene under highly dilute conditions has afforded the title compound (4), which has been found to exist in a stepped anti conformation.

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Report | Regular issue | Vol 12, No. 10, 1979, pp. 1335 - 1337
Published online:
DOI: 10.3987/R-1979-10-1335
A Novel Reaction of Dichlorocarbene with 2-Chlorosubstituted Nitrogen Heteroaromatic Bases under Phase Transfer Conditions

Anna Arnoldi, Remo Galli,* and Angela Zagni

*Laboratorio di Chimica Organica, Facoltà di Agraria, Istituto di Biochimica Generale, Università digli Studi di Milano, via Celoria 2, 20133 Milano, Italy


Some 2-chlorosubstituted heteroaromatic bases, under phase-transfer catalysis conditions, suffer the attack of dichlorocarbene and the substitution of the chlorine giving rise to the corresponding N-dichloromethyl-2-oxo-derivatives.

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Report | Regular issue | Vol 12, No. 10, 1979, pp. 1339 - 1341
Published online:
DOI: 10.3987/R-1979-10-1339
A New Route for Synthesis of 4 (or 5)-Propylimidazole

Ashutosh, N. D. Pandey, and J. K. Mehrotra*

*Chemical Laboratories, M. N. R. Engineering College, Allahabad 211004, India


Ethyl 1-ethyl-3-phthalimidoacetate was prepared by condensation of ethyl 3-phthalimidoacetoacetate and acetaldehyde followed by reduction. The substituted acetoacetate was hydrolysed by dil.HCl and the corresponding aminoketone treated with potassium thiocyanate to yield 2-mercapto-4 (or 5)-propylimidazole. The later was oxidised to the corresponding imidazole.

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Review | Regular issue | Vol 12, No. 10, 1979, pp. 1343 - 1368
Published online:
DOI: 10.3987/R-1979-10-1343
Synthetic Reactions Using Isoxazole Compounds

Choji Kashima*

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


The activation of C-5 methyl group of 3,5-dimethylisoxazoles is discussed by MINDO/2 calculation and H-D exchange reaction. The regioselective substitution reaction of 5-methylisoxazoles with electrophiles such as alkyl halides, carbon dioxide, carbonyl compounds, Schiff bases, nitriles, nitrites and nitroso compounds is reviewed. Also the conversions of resulting isoxazole derivatives to β-diketones, enones and some heterocyclic compounds are reviewed.

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17 data found. 1 - 17 listed