Regular Issue

Vol. 6, No. 4, 1977

18 data found. 1 - 18 listed
Communication | Regular issue | Vol 6, No. 4, 1977, pp. 379 - 382
Published online:
DOI: 10.3987/R-1977-04-0379
Reaction of Pyrisinium and Isoquinolinium N-Imines with Ketenethihoacetals

Hiroshi Fujito, Yoshinori Tominaga, Yoshiro Matsuda, and Goro Kobayashi*

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


Pyridinium and isoquinolinium N-vinylimine and azaindolizine derivatives were synthesized by a reaction of pyridinium and isoquinolinium N-imine with ketenethioacetals.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 383 - 386
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DOI: 10.3987/R-1977-04-0383
Rearrangement of 9-Alkyltheophyllines to the 7-Alkyl amalogues

John H. Lister*

*John Curtin School of Medical Research, Canberra City 2601, Australia


Under thermal conditions 9-benzyltheophylline (1) with either benzyl bromide or hydrobromic acid undergoes rearrangement in dimethylformamide to the 7-benzyl isomer (3).

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 387 - 390
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DOI: 10.3987/R-1977-04-0387
Convenient Synthesis of S-Containing Heterobicycles

Shiro Ikegami,* Jun-ichi Ohishi, and Yasuo Shimizu

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1, Sagamiko, Kanagawa 199-0195, Japan


6-exo-Chloro-2-thiabicyclo[2.2.l]heptane and its 1-methyl analog, and 4-exo-chloro-6-thiabicyclo[3.2.1]octane are synthesized by the intramolecular cyclization of sulfenyl chlorides formed in situ from the reaction of the corresponding cycloalkenyl disulfides with chlorine.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 391 - 394
Published online:
DOI: 10.3987/R-1977-04-0391
A New Synthesis of (±)-7-Epideoxynupharidine and (±)-1-Epi-7-epideoxynupharidine

Shingo Yasuda, Miyoji Hanaoka, and Yoshio Arata*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


The Mannich reaction of the amino-ketone (VIII) with 3-furylaldehyde followed by the isomerization afforded stereoselectively the trans-quinolizidine (X), the Wolff-Kishner reduction of which provided (±)-7-epi- and (±)-1-epi-7-epideoxynupharidine (I and II).

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 395 - 397
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DOI: 10.3987/R-1977-04-0395
Nitrous Acid Deamination of (R)-β-Aminoadipic Acid

Toshio Wakabayashi* and Yoshinori Kato

*Bio-Medical Research, Teijin Institute, Asahigaoka 4-3-2, Hino, Tokyo 191, Japan


Intramolecular participation by carboxyl group in diazotization processes has received much attention. The deamination of (R)-β-aminoadipic acid in aqueous nitrous acid affords (S)-carboxymethylbutanolide (2) with 69% net inversion.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 399 - 404
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DOI: 10.3987/R-1977-04-0399
Thalipine, a New Aporphine-benzylisoquinoline Alkaloid

M. Shamma,* J. L. Moniot, and P. Chinnasamy

*Department of Chemistry, The Pennsylvania State University, York Campus, P1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.


(+)-Thalipine (1) has been obtained from Thalictrum polygamum Muhl. Like most other alkaloids of this plant, it is derived biogenetically from (+)-reticuline without recourse to O-demethylation.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 405 - 410
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DOI: 10.3987/R-1977-04-0405
Alkaloids of Thalictrum. XIX. Revolutopine and Thelipine, New Arophinebenzylisoquinoline Dimers from Thalictrum revolutum

Jinn Wu, Jack L. Beal, Wu-Nan Wu, and Raymond W. Deskotch*

*Division of Pharmacognosy and Natural Products Chemistry, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, U.S.A.


Revolutopine and thalipine, new alkaloids from the tops of Thalictrum revolutum have been assigned the aporphine-benzylisoquinoline structures 1 and 2 on the basis of physical and chemical evidence.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 411 - 414
Published online:
DOI: 10.3987/R-1977-04-0411
2-Substituted Acenaphtho[1,2-d]oxazoles

Otohiko Tsuge* and Masahiro Koga

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


Irradiation of 2-diazoacenaphthenone (1) in nitriles such as acetonitrile, propionitrile, benzonitrile, p-tolunitrile, and acrylonitrile afforded the corresponding 2-substituted acenaphtho[l,2-d]oxazoles (3). In pyrolysis of 1 in benzonitrile 2-phenyloxazole derivative 3c was formed, together with traces of 2,2’-diacenaphthylidene-1,1’-dione.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 415 - 421
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DOI: 10.3987/R-1977-04-0415
Biotransformation of Reticuline into Morphinandienone, Aporphine, and Protoberbaerine Alkaloids with Rat Liver Enzyme

Tetsuji Kametani,* Yohko Ohta, Makoto Takemura, Masataka Ihara, and Keiichiro Fukumoto

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


(±)-Reticuline (1a) was biotransformed into morphinandienone alkaloid, pallidine (4a), and aporphine alkaloid, isoboldine (5a) in addition to protoberberine alkaloids, coreximine (3a) and scoulerine (2a). The transformation was stimulated by the presence of the following cofactors, NAD, NADP or NADPH. Deuterium labelled experiment revealed that the N-methyl group of (±)-reticuline was not intactly incorporated into protoberberines.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 423 - 429
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DOI: 10.3987/R-1977-04-0423
Photochemical Reactions of 2-Benzylidenehydrazinopyrimidines

Teruaki Tsujikawa* and Motomi Tatsuta

*Central Research Division, Takeda Chemical Industries, Ltd., 17-85 Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan


Under a nitrogen atmosphere, anti-isomers of 2-benzylidenehydrazinopyrimidines easily underwent isomerization to their syn-isomers by irradiation with an ultraviolet light over a benzene solution, but in thb presence of oxygen, photosensitized auto-oxidation occurred to afford 3-aryl-1,2,4-triazolo[4,3-a]pyrimidines. When irradiated in the same manner, 2-benzylidenehydrazino-1,3,5-triazine derivative decomposed into benzaldehyde and 2-hydroxy-1,3,5-triazine.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 431 - 434
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DOI: 10.3987/R-1977-04-0431
A Synthesis of Flavins by the Reaction of 6-(N-Alkylanilino)-5-nitrouracils with Diethyl Azodicarboxylate in the Presence of Base

Fumio Yoneda* and Yoshiharu Sakuma

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan


The treatment of 6-(N-alkylanilino)-5-nitrouracils with diethyl azodicarboxylate (DAD) in the presence of bases gave the corresponding isoalloxazines (flavins).

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 435 - 442
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DOI: 10.3987/R-1977-04-0435
Studies on the Synthesis of Bisindole Alkaloids. IX. The Synthesis of Novel Vindoline Derivatives

James P. Kutney,* Ka Kong Chan, William B. Evans, Yutaka Fujise, Toshio Honda, Frederick Karl Klein, and Joao Pedro de Souza

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada


A detailed study involving the degradation of vindoline (1) provides a series of novel vindoline derivatives which are important intermediates in the synthesis of bisindole alkaloids.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 443 - 448
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DOI: 10.3987/R-1977-04-0443
Studies on the Synthesis of Bisindole Alkaloids. X. The Synthesis of Novel Vinblastine Derivatives

James P. Kutney,* William B. Evans, and Toshio Honda

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada


The coupling of catharanthine-Nb-oxide with various novel vindoline derivatives provides a series of novel vinblastine derivatives. These compounds provide an opportunity to evaluate the importance of the functionality in the dihydroindole unit of the bisindole system in terms of anti-tumor activity.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 449 - 457
Published online:
DOI: 10.3987/R-1977-04-0449
Pteridines. Part XLII. Synthesis of Some Banzo[g]pteridines. A Novel Aromatization Reaction

Edward C. Taylor* and John V. Berrier

*Department of Chemistry, Princeton University , Princeton, New Jersey 08544, U.S.A.


Condensation of 6-chloro-2-oximinocyclohexanone with aminomalononitrile gave 2-amino-3-cyano-5-chloro-5,6,7,8-tetrahydroqinoxaline 1-oxide (1), which upon heating in acetic acid underwent a novel aromatization reaction, with loss of HCl and H2O, to give 2-amino-3-cyanoquinoxaline (3). An analogous aromatization reaction was observed with 3-amino-2-cyano-5,6-dihydrobenzo(h)quinoxaline 1-oxide (9), which gave 3-amino-2-cyanobenzo(h)quinoxaline (10) upon heating with a trace of HCl or H2SO4. These o-aminonitriles were then converted to variously substituted fused pteridine derivatives by conventional cyclization techniques.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 459 - 462
Published online:
DOI: 10.3987/R-1977-04-0459
Electro-oxidation of 1-Phenethylisoquinolines

Ahmad Najafi and Malcolm Sainsbury*

*School of Chemistry, University of Bath, Bath, Avon. BA2 7AY, U.K.


An examination of methoxylated derivatives of 1-phenethylisoquinoline has shown that the mode of eleotrochemical oxidation undergone by such compounds is different to that exhibited by analogous 1-benzylisoquinolines: in particular, intramolecular cyclisation through C-C bond formation is not observed.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 463 - 467
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DOI: 10.3987/R-1977-04-0463
Neopelline. A Partial Synthesis of 8-Acetyl-14-benzoylneoline

S. William Pelletier,* J. Bhattacharayya, and Naresh V. Mody

*Department of Chemistry, Institute for Natural Products Research, The University of Georgia, Chemistry Building, Athens, Georgia 30602-2556, U.S.A.


A synthesis of 8-acetyl-14-benzoylneoline has been effected in five steps from the known alkaloid, delphisine. On the basis of the reported data for “neopelline”, the suggested structure of 8-acetyl-14-benzoylneoline is in error and the existence of “neopelline” in nature is doubtful.

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Communication | Regular issue | Vol 6, No. 4, 1977, pp. 469 - 474
Published online:
DOI: 10.3987/R-1977-04-0469
Reaction of N-Benzenesulfonyl-9-azabicyclo[3.3.1]nona-2,6-diene with Diborane: Failure of Cyclic Hydroboration in the Intramolecularly Faces Diene System

Takefumi Momose* and Shohgo Atarashi

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan


Hydroboration of N-benzenesulfonyl-9-azabicyclo[3.3.1] nona-2,6-diene gave 2,6-diols and exo,exo-2,7-diol in the ratio of ca. 2.3 : 1, but neither exo,exo-3,7-diol nor the products derived from a boraadamantane were formed. A marked site-selectivity in the hydroxylation was discussed in terms of inductive or spatial effects of the N-substituent.

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Review | Regular issue | Vol 6, No. 4, 1977, pp. 475 - 497
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DOI: 10.3987/R-1977-04-0475
Pseudobase Formation from Quaternary Pyridinium, Quinolinium and Isoquinolinium Cations

Vilím Simánek* and Vladimír Preininger

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


A review of recent studies of addition reactions of the hydroxide ion with some quaternary aromatic nitrogen compounds has been presented.

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18 data found. 1 - 18 listed