Regular Issue

Vol. 12, No. 2, 1979

10 data found. 1 - 10 listed
Communication | Regular issue | Vol 12, No. 2, 1979, pp. 217 - 225
Published online:
DOI: 10.3987/R-1979-02-0217
Photocyclization and Photooxygenation of 1,3,4,5-Tetraarylimidazolin-2-ones

Otohiko Tsuge,* Koji Oe, and Hisataka Inoue

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


Irradiation of 1,3,4,5-tetraarylimidazolin-2-ones in benzene, under nitrogen, with or without iodine gave the corresponding phenanthroimidazolinones. In the presence of oxygen, however, the imidazolinone was photochemically converted to the corresponding benzanilide, N-benzoyl-N ,N’-diphenylbenzamidine and p-benzoylphenyl isocyanate, besides the phenanthroimidazolinone. On the other hand, the dye-sensitized photooxygenation afforded the benzanilide, amidine, N,N’-dibenzoyl-N,N’-diphenylurea, and/or 1,4-diaza-1,3-butadiene derivative, whose yields depended on the nature of substituents of the imidazolinone and of the solvent employed. Mechanistic consideration of the photooxygenation was also described.

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Communication | Regular issue | Vol 12, No. 2, 1979, pp. 227 - 230
Published online:
DOI: 10.3987/R-1979-02-0227
A Facile Method for the Preparation of 4-Nitropyridine and -quinoline Derivatives: Reduction of Aromatic Amine N-Oxides with Trimethylphosphite under Irradiation

Chikara Kaneko,* Atsushi Yamamoto, and Michiko Gomi

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


Irradiation (> 300 nm) of pyridine and quinoline 1-oxides having a nitro group at the 4-position in dichloromethane containing trimethylphosphite of relatively high concentration (> 10-2mol/l) resulted in an almost quantitative formation of the deoxygenated products.

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Communication | Regular issue | Vol 12, No. 2, 1979, pp. 231 - 237
Published online:
DOI: 10.3987/R-1979-02-0231
Cycloaddition Reactions of Diphenylketene with 1-Aza-1,3-diene and Conjugated Sulfilimines

Masanori Sakamoto,* Kyoko Miyazawa, Keiko Kuwabara, and Yoshio Tomimatsu

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


The cycloaddition reactions of diphenylketene (I) with several azadienes have been examined. 2-Styrylthiazoline (IIa-c) and I generally underwent a 4+2 cycloaddition to give thiazolo[3,2-a]pyridines (IIIa-c). On the other hand, reaction of I with 2-styrylquinoline and 2-styrylpyridine gave rise to a 2+2+2 cycloaddition products (Va, b), respectively. Similar reaction of I with 6-styrylphenanthridine gave pyrido[1,2-f]phenanthridine (VII) and a lactone (Vc).
The orientation of the addition products of I with sulfilimines (VIII, XI, XII) which we reported in our previous paper was the error and the reverse.

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Communication | Regular issue | Vol 12, No. 2, 1979, pp. 239 - 242
Published online:
DOI: 10.3987/R-1979-02-0239
A Synthesis of 3-Hydroxyiminoacryl-4-quinazolines and Transformation into 1,2,4-Oxadiazoles

Katsuhiko Nagahara* and Atsushi Takada

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


Treatment of N-hydroxyiminobenzyl-2-aminobenzamides (I) with ortho esters afforded the corresponding 2-alkyl-3-hydroxyiminoacyl-4-quinazolones (II) and 3,5-diaryl-1,2,4-oxadiazoles (III), respectively. Furthermore, treatment of II with ethanolic hydrochloric acid caused the ring transformation to give the corresponding III.

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Communication | Regular issue | Vol 12, No. 2, 1979, pp. 243 - 246
Published online:
DOI: 10.3987/R-1979-02-0243
An Azabycyclo[3.3.1]nonanone Apprpach to Tecoma Alkaloids: A Stereoselective Synthesis of (±)-7-Demethyltecomanine

Takefumi Momose,* Masahiko Kinoshita, and Takeshi Imanishi

*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


A stereoselective synthesis of (±)-7-demethyltecomanine (2) via a 3-azabicyclo[3.3.1]nonane precursor (4) which has the same configuration at the 3,5-position on the piperidine ring as that for tecomanine (1) is described.

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Communication | Regular issue | Vol 12, No. 2, 1979, pp. 247 - 251
Published online:
DOI: 10.3987/R-1979-02-0247
Biotransformation of Some 2-Methylpapaverinium Derivatives with Rat Liver Enzymes in Vitro

Dana Walterová,* Alice Nemecková, Vladimír Preininger, Vilím Simánek, and Ladislav Dolejs

*Institute of Medical Chemistry, Palacky University, 3, Hnevotínská, 775 15 Olomouc, Czech Republic


2-Methyl-3,4-dihydropapaverinium derivatives (1-3) and 2-methylpapaverinium chloride (4) have been converted into the corresponding isoquinolones and carbonyl compounds by incubation with rat liver preparations. The role of pseudobase formation in this biotransformation is discussed.

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Report | Regular issue | Vol 12, No. 2, 1979, pp. 253 - 257
Published online:
DOI: 10.3987/R-1979-02-0253
Reaction of Citral with Homophthalic Anhydrides

Suneel Y. Dike and Jaysukhlal R. Merchant*

*Department of Organic Chemistry, Institute of Science, 15, Madam Cama Road, Bombay-400 032, India


Syntheses of 2-methyl-2-(4-methylpent-3-enyl)-5-(2-carboxyphenyl)-pyran-6-one from homophthalic acid and anhydrides with citral is described.

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Report | Regular issue | Vol 12, No. 2, 1979, pp. 259 - 261
Published online:
DOI: 10.3987/R-1979-02-0259
The Reaction of 4-Hydroxycoumarin with Acetic Anhydride and Pyridine

V. K. Ahluwalia,* Devendra Kumar, and Suman Mehta

*Department of Chemistry, University of Delhi, Delhi-110 007, India


The reaction of 4-hydroxycoumarin (I) with acetic anhydride - pyridine afforded 4-acetoxy-3-(N-acetyl-1’,2’-dihydro-2’-pyridyl)coumarin (III) in contrast to the expected 4-acetoxycoumarin (IV). The structure of compound has been established spectroscopically.

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Report | Regular issue | Vol 12, No. 2, 1979, pp. 263 - 268
Published online:
DOI: 10.3987/R-1979-02-0263
Reactions of Azepine and Diasepine Derivatives with Chlorosilanes in the Presence of Magnesium: 4,5-Double Addition Reactions to Azepine Derivatives

Katsuhiro Saito* and Kensuke Takahashi

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


The reactions of 1-ethoxycarbonyl-1H-azepine (1) and chlorosilanes (Xa-c) in HMPA in the presence of magnesium afforded 1:2 adducts, trans-4,5-disubstituted-4,5-dihydroazepines (2a-c), which upon heating gave siloxane derivatives (3a-b) almost quantitatively. In the same reactions with 1-ethoxycarbonyl-1H-1,2-diazepine (8), a nitryl compound (9) was obtained. The dihydroazepines and the nitryl compound are considered to be formed via radical anions 5 and 10, respectively.

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Review | Regular issue | Vol 12, No. 2, 1979, pp. 269 - 299
Published online:
DOI: 10.3987/R-1979-02-0269
Absorption Spectra of Phytoxanthones

M. Afzal,* Jassim M. Al-Hassan, and Farida N. Al-Masad

*Biochemistry Department, Kuwait University, Safat 13060 P.O. Box 5969, Kuwait


The Ultraviolet Absorption Spectra of Phytoxanthones are reviewed.

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10 data found. 1 - 10 listed