Regular Issue

Vol. 16, No. 4, 1981

24 data found. 1 - 24 listed
Communication | Regular issue | Vol 16, No. 4, 1981, pp. 521 - 524
Published online:
DOI: 10.3987/R-1981-04-0521
Synthesis of 17β-Pyridyl- and 17β-Pyridonyl-androstane Derivatives

Jerzy Wicha* and Marek Masnyk

*Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O.Box 58, PL-01-224 Warszawa 42, Poland


Bufadienolide analogues 11 - 14 were synthesized from the 17-oxocompound 3.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 525 - 528
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DOI: 10.3987/R-1981-04-0525
Preparation of 2S-Dioxo Isosters of N-Methylated Isoguanines

Pilar Goya, Carmen Ochoa, and Manfred Stud*

*Instituto de Química Médica, C. S. I. C., Calle Juan de la Cierva 3, E-28006 Madrid, Spain


Preparation of 7-amino-3,6-dimethylimidazo[2,3-c]-1,2,6-thiadiazine 5,5-dioxide which involves formylation of the corresponding furazano[3,4-c]thiadiazine derivative, reductive cleavage of the furazan moiety and subsequent cyclization to the imidazole ring is described. For the synthesis of 1-methyl- and 3-methyl-7-amino-4H-imidazo[2,3-c]-1,2,6-thiadiazine 5,5-dioxide, the corresponding 4-benzyl-imidazo[2,3-c]thiadiazine was prepared and methylated to give a mixture of the 4-benzyl-1-methyl and 4-benzyl-3-methyl isomers which were finally debenzylated by catalytic hydrogenation. The structures of the newly synthesized compounds are discussed on the basis of their spectroscopic data.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 529 - 531
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DOI: 10.3987/R-1981-04-0529
Zur Struktur und Stereochemie des Clivojulins aus Clivia niniata Regal

Werner Döpke* and Sial Ali Roshan

*Sektion Chemie, Universität zu Berlin, Humboldt, Germany


The structure, stereochemistry and fragmentation of the new alkaloid Clivojuline is described.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 533 - 536
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DOI: 10.3987/R-1981-04-0533
Structure and Synthesis of 6-Iminosanguinarine, a New Benzophenanthridine Artefact

Luis Castedo,* Domingo Domínguez, Manuel Pereira, Jósé Saá, and Rafael Suau

*Facultad de Química y Sección de Alcaloides, Deparamento de Química Orgánica, C. S. I. C., Santiago de Compostela, Spain


6-iminosanguinarine (5), a novel benzophenanthridine artefact was isolated from the roots of Glaucium flavum Cr. var. vestitum. The structure was determined by spectral data and synthesis.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 537 - 538
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DOI: 10.3987/R-1981-04-0537
Cycloaddition of Thiazolo[3,2-a]benzimidazole and Imidazo[2,1-b]benzothiazole with Methyl Propiolate; Formation of Thiazolo[3,2-a][1,5]benzodiazepine and [1,4]Diazepino[7,1-b]benzothiazole

Noritaka Abe* and Tarozaemon Nishiwaki

*Department of Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan


3-Methylthiazolo[3,2-a]benzimidazole and 2-methylimidazo[2,1-b]benzothiazole, respectively, react with methyl propiolate to give 1:2-adducts which are characterized as methyl (Z)-11-(methoxycarbonyl)-3-methyl-10-thiazolo[3,2-a][1,5]benzodiazepinacrylate and methyl (Z)-5-(methoxycarbonyl)-2-methyl-4-[1,4]diazepino[7,1-b]benzothiazolacrylate.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 539 - 547
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DOI: 10.3987/R-1981-04-0539
Stereoselective Conversions of cis-4-(2’,2’-Dimethoxyethyl)-3-[(1’S*)-1’-hydroxyethyl]-2-azetidinone into the Corresponding trans-(1’R*)- and (1’S*)-Azetidinones

Tetsuji Kametani,* Takayasu Nagahara, and Masataka Ihara

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


Stereoselective conversions of cis-4-(2’,2’-dimethoxyethyl)-3-[(1’S*)-1’-hydroxyethyl]-2-azetidinone into the corresponding trans-(1’R*)- and (1’S*)-azetidinones were achieved by the modification of the Merck’s method. Furthermore, selective protection of the secondary amide group of the β-lactam ring and the hydroxyl group on the same molecule with dimethyl-tert.-butylsilyl group is also described.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 549 - 554
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DOI: 10.3987/R-1981-04-0549
Cyclohexadienones. 5. Reaction of 4-Halo-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-ones with Imidazoles

Gouki Fukata, Takashi Itoh, and Masashi Tashiro*

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


Reactions of 4-bromo-(1a) and 4-chloro-2,4,6-tri-t-butyl-2,5-cyclohexadien-1-one (1b) with imidazole (6b), 1-methyl-(6a), 2-methyl-(6c), 4-methylimidazole (6d), benzimidazole (6e), and 2-methylbenzimidazole (6f) were carried out under various conditions. It was found in these reactions that many products such as the 1-(4-oxo-2,5-cyclohexadienyl)-, 1-(2-hydroxyphenyl)- and 1-(4-hydroryphenyl)imidazoles were formed and that the type of the products depended upon the structures of imidazoles 6.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 555 - 558
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DOI: 10.3987/R-1981-04-0555
Erythlaurine and Erythramide, Two New Erythrinan Alkaloids Possessing a Directrly Attached C1-Unit to the Aromatic Ring

Motoharu Ju-ichi,* Yukari Fujitani, Tetsuro Shingu, and Hiroshi Furukawa

*Faculty of Pharmaceutical Science, Mukogawa-Women’s University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan


Two new erythrinan alkaloids named erythlaurine and erythramide were isolated from the leaves of Cocculus laurifolius DC. (Menispermaceae) and their structures were elucidated by chemical and spectral studies as (1) and (2), respectively.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 559 - 561
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DOI: 10.3987/R-1981-04-0559
A New Synthesis of Pyrimido[5,4-e]-as-triazine Derivatives

Keitaro Senga* and Sadao Nishigaki

*Pharmaceutical Institute, School of Medicine, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan


The reaction of 5-arylazo-6-arylidenehydrazino-1,3-dimethyluracils (II), prepared by the diazotization of 6-arylidenehydrazino-1,3-dimethyluracils (I), with dimethylformamide dimethylacetal afforded the corresponding 3-arylfervenulins (3-aryl-6,8-dimethylpyrimido[5,4-e]-as-triazine-5,7(6H, 8H)-diones) (V).

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 563 - 571
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DOI: 10.3987/R-1981-04-0563
Synthesis of 2-Amino-6-phenyl-4(3H)-pyrimidinone-1-oxide

Wendell Wierenga,* Harvey I. Skulnick, Robert L. Dow, and Constance G. Chidester

*Experimental Chemistry Researchm Physical and Analytical Chemistry Rresearch, The Upjohn Company, Kalamazoo, Michigan 49001, U.S.A.


Introduction of a 2,4-dichlorophenoxy group at the 4-position of 2-amino-6-phenylpyrimidine allowed a regioselective oxidation to the N1-oxide. The resultant pyrimidine oxide, derived from m-chloroperoxybenzoic acid treatment, was converted to the pyrimidinone by acidic hydrolysis. The structure was unambiguously determined by x-ray crystallographic analysis.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 573 - 576
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DOI: 10.3987/R-1981-04-0573
Oxidation of 2,4-Disubstituted Pyrimidines with Organic Peracids

Hiroshi Yamanaka,* Shigeru Ogawa, and Takao Sakamoto

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


While 4,6-disubstituted (alkyl, aryl, alkoxyl) pyrimidines easily afforded the corresponding mono-N-oxides with hydrogen peroxide in glacial acetic acid, pyrimidine derivatives whose 6-position is free, are partly oxidatively degradated during N-oxidation reaction. The oxidation of the latter compounds under the above conditions gave 2,4-disubstituted imidazoles together with their mono-N-oxides. A likely mechanism of this ring-contraction and the improved conditions for the synthesis of the N-oxides are also described.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 577 - 580
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DOI: 10.3987/R-1981-04-0577
Reaction of 3-Aminocrotonamide with Nitriles

Tetsuzo Kato,* Takuo Chiba, and Makoto Sasaki

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


The reaction of 3-aminocrotonamide (5) with some nitriles, such as acetonitrile, propiononitrile, iso-butyronitrile, and benzonitrile, gave the corresponding 2-substituted 6-methyl-4(3H)-pyrimidones (2a - 2d). Phenylacetonitrile reacted with (5) to give 2-benzyl-6-methyl-4(3H)-pyrimidone (7) and 6-amino-4-methyl-5-phenyl-2(1H)-pyridone (8a). Malononitrile, however, reacted with (5) to afford 6-amino-5-cyano-4-methyl-2(1H)-pyridone (8b).

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 581 - 590
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DOI: 10.3987/R-1981-04-0581
Oxidation of the 2,16 Double Bond of Vincadifformine

Georgette Hugel, Jean-Yves Laronze, Jacqueline Laronze, and Jean Lévy*

*Facluté de Pharmacie, UPRES-A/CNRS 6013, Insitut des Biomoleculés, 51, rue Cognacq-Jay, F-51096 Reims Cedex, France


Chemical vs photochemical oxidation of the 2,16 double bond of vincadifformine 1 and 3-oxo vincadifformine 2 yielded inter alia, respectively the ketoöxindoles 7 and 8. Attempts of partial synthesis of vincatine 15 from these derivatives were unsuccessful. The structure of the LAH reduction product of vincatine is revised to 21. The stereochemical course of an earlier total synthesis of vincadifformine is examined.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 591 - 594
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DOI: 10.3987/R-1981-04-0591
Total Synthesis of Optically Active Protoberberine Alkaloid, Xylopinine, by 1,3-Asymmetric Induction in Photolysis

Tetsuji Kametani,* Nanami Takagi, Masahiro Toyota, Toshio Honda, and Keiichiro Fukumoto

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


Total synthesis of optically active xylopinine (11) was achieved by irradiation of the enamide (4) as a key reaction.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 595 - 598
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DOI: 10.3987/R-1981-04-0595
Ring Transformations of 4-Aryl-3-haloacylthio-3-isothiazoline-5-thiones as a New Access to the 4(5H)-Thiazolone and 5,6-Dihydro-4H-1,3-thiazin-4-one Rings

Tarozaemon Nishiwaki,* Etsuko Kawamura, Noritaka Abe, Hirafumi Kochi, Yoshiro Sasaoka, and Kazumi Soneda

*Department of Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan


The reactions of 4-aryl-3-haloacylthio-3-isothiazoline-5-thiones with reactive acetylenes (e.g. dimethyl acetylenedicarboxylate and dibenzoylacetylene) afford 2-[1,3-dithiol-2-ylidene(aryl)methyl]-4(5H)-thiazolones and 5,6-dihydro-2-[1,3-dithiol-2-ylidene(aryl)methyl]-4H-1,3-thiazin-4-ones mostly in high yields.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 599 - 603
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DOI: 10.3987/R-1981-04-0599
Synthesis of 1-Oxa Analogues of Naturally Occurring Cephalosporins and Cephamycins

Yuji Sendo,* Toshiro Konoike, Masayuki Murakami, and Mitsuru Yoshioka

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


The title compounds 15a-c and 16a-c were synthesized from a 3-exomethylene-1-oxacepham compound 4. Its chlorohydroxylation provided a key intermediate 5e in synthesis of the 3’-oxygen-functionalized 1-oxacephems.

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Communication | Regular issue | Vol 16, No. 4, 1981, pp. 605 - 608
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DOI: 10.3987/R-1981-04-0605
An Efficient Synthesis of cis-Oxabicyclo[3.3.0]oct-6-en-3-one

Seiichi Takano,* Chiyoshi Kasahara, and Kunio Ogasawara

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


An efficient synthesis of a prostaglandin synthon (±)-cis-oxabicyclo[3.3.0]oct-6-en-3-one (1) has been developed using cyclopentadiene (2) as starting material. Employing the same methodology optically active (1) is also synthesized in low optical purity.

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Report | Regular issue | Vol 16, No. 4, 1981, pp. 609 - 611
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DOI: 10.3987/R-1981-04-0609
A New Synthesis of 1,4-Dihydro-3(2H)-isoquinolinones by the Cyclization of N-Hydroxymethylarylacetamides

Yasuo Watanabe,* Yasuko Komachi, and Tokumitsu Miyazaki

*Daiichi College of Pharmaceutical Sciences, 22-1 Tamagawa-cho, Minami-ku, Fukuoka 815-0037


A new and facile synthesis of 1,4-dihydro-3(2H)-isoquinolinones by the intramolecular amidomethylation with pyrophosphoric acid is described.

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Report | Regular issue | Vol 16, No. 4, 1981, pp. 613 - 620
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DOI: 10.3987/R-1981-04-0613
Synthetic Studies on Tetrapenoids — Part IV. Synthesis of (±)-Podocarpa-8,11,13-triene-13-methoxy-19,20-dioic Acid

Ajoy K. Banerjee* and Héctor E. Hurtado

*Centro de Química, Instituto Venezolano de Investigaciones Científicas, I.V.I.C., Apartado 21827, Caracas 1020-A, Venezuela


An alternate approach for the titled compound (I), a potential intermediate for the synthesis of racemic atisine and veatchine is described.

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Report | Regular issue | Vol 16, No. 4, 1981, pp. 621 - 629
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DOI: 10.3987/R-1981-04-0621
Studies on Thioquinazolinones and Synthesis of 9-Iodo-3,4-diphenyl[1,2,4,5]tetrazepino[3,2-b]quinazolin-7(1H)-one

M. R. Chaurasia and Surendra K. Sharma*

*Department of Chemistry, D. A. V. (P. G.) College, Dehra Dun, India


Various 6,8-disubstituted 3 (aryl) or (alkyl)-2s-(substituted)-4(3H)-quinazolinones, 6-bromo-2-methyl-4-s-(substituted)-4(3H)-qinazolin ones, bis(6,8-dibromo-3-benzyl-4-oxo-quinazolin-2-yl)disulphide, 9-iodo-3,4-diphenyl[1,2,4,5]tetrazepino(3,2-b)quinazolin-7(1H)-one and 6-iodo-2-(p-methylphenylamino)-4H-3,1-benzothiazin-4-one have been prepared. Their structures have been established on the basis of various studies.

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Report | Regular issue | Vol 16, No. 4, 1981, pp. 631 - 635
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DOI: 10.3987/R-1981-04-0631
Kinetics of Alkylation Reactions of Pyrrolizidine Alkaloid Derivatives

Joseph J. Karchesy and Max L. Deinzer*

*College of Veterinary Medicine, Oregon State University, Gilbert Hall 153, Corvallis Oregon 97331, U.S.A.


Comparison is made of the alkylating activities of a series of semi-synthetic pyrrole esters and pyrrole derivatives of pyrrolizidine alkaloids under pseudo-first-order reaction conditions. Examination of the rate data indicates two reaction patterns; those compounds whose rate data fit a simple first-order rate expression and a second group of compounds whose rate data fit a biexponential expression.

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Report | Regular issue | Vol 16, No. 4, 1981, pp. 637 - 639
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DOI: 10.3987/R-1981-04-0637
Oxidative Cyclization of 3-Cinnamoyltropolones with Manganese(III) Acetate and Lead(IV) Acetate

Kimiaki Imafuku,* Kazunori Suezaki, and Hisashi Matsumura

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


3-Cinnamoyltropolones (1a-i) were oxidized with manganese(III) acetate and lead(IV) acetate to give 2-arylidene-3,8-dihydro-2H-cyclohepta[b]furan-3,8-diones (4a-i), which have an aurone-like structure.

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Report | Regular issue | Vol 16, No. 4, 1981, pp. 641 - 644
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DOI: 10.3987/R-1981-04-0641
Synthese Eines Neuen “Push-Pull”-stabilisierten Molekülsystems mit Zentraler Bicyclo[4.4.1]undeca-1(10),3,5,8-tetraen-2,7-diyliden-gruppe

Richard Neidlein* and Hartmut Zeiner

*Pharmazeutisch-Chemishces Institut, Universität Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany


The violet title compound (3) has been synthesized from the bis-thioacetal (4) in two steps, the last of which involves a based catalyzed vinylogous Pummerer dehydration of a sulfoxide. Some chemical and physical properties of (3), which may be viewed as a “push-pull” stabilized quinodimethane, are described.

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Report | Regular issue | Vol 16, No. 4, 1981, pp. 645 - 646
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DOI: 10.3987/R-1981-04-0645
Partial Synthesis of Baloxine

Catherine Caron, Louisette Le Men-Olivier, Michel Plat and Jean Lévy*

*Laboratoire d’Isolement, Transformation et Synthese de Substances Naturelles, UFR de Pharmacie, associe au CNRS, Université de Champagne-Ardenne, 51 rue Cognacq-Jay-F 51096 Reims Cedex, France


Baloxine 1 (19S-hydroxy 14-oxo vincadifformine) was obtained from vindolinine 2.

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24 data found. 1 - 24 listed