Regular Issue

Vol. 16, No. 11, 1981

25 data found. 1 - 25 listed
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1855 - 1857
Published online:
DOI: 10.3987/R-1981-11-1855
First Examples of Isoxazolidin-4-ones

Anup Bhattacharjya*

*Department of Chemistry, Washington University, St. Louis, Missouri 63130, U.S.A.


First examples of isoxazoldin-4-ones were prepared from 2,4-dibromo-2,4-dimethylpentan-3-one and hydroxylamine and N-acylhydroxylamines.

PDF (80KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1859 - 1862
Published online:
DOI: 10.3987/R-1981-11-1859
Structure-activity Relationships of Oxygenated Morphinas. II. Synthesis and Biological Properties of 4-Methoxymorphinan-6-ones with Narcotic Antagonist Side-chains on Nitrogen

Helmut Schmidhammer, Arthur E. Jacobson, Louise Atwell, and Arnold Brossi*

*Laboratoryof Chemistry, Medical Chemistry Section, National Arthritis Institute, National Institute of Health, Behesda, Maryland 20892, U.S.A.


The synthesis of narcotic antagonists from the 4-methoxymorphinan-6-one series is described. The synthesis started from optically active 4-hydroxy-6-keto-N-formylmorphinan prepared from morphine, by employing conventional procedures. The compounds have pentazocine-like agonist activity and N-cyclopropylmethyl-4-methoxymorphinan-6-one is somewhat more potent than nalorphine as a narcotic antagonist.

PDF (79KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1863 - 1871
Published online:
DOI: 10.3987/R-1981-11-1863
Isomerization and Hydrogenation of Nitrogen-containing Organic Compounds Catalyzed by Heterogeneous Catalysts

Hideshi Hattori and Kozo Tanabe*

*Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan


The double-bond isomerization of 1-N-pyrrolidino-2-propene and N,N-dimethyl-2-propenylamine were studied at 40°C over MgO, CaO, SrO, BaO, La2O3, ThO2, ZrO2, ZnO etc. It was found that MgO and CaO which have strong basic sites on the surfaces exhibited a high catalytic activity, the selectivity for the formation of 1-N-pyrrolidino-1-propene being more than 80 %. The double-bond migration of the allylamines is suggested to proceed via anionic intermediates in which the cis form is much more stable than the trans form. For the hydrogenation of N,N-dimethyl-2-propenylamine, the activity as well as the selectivity of nickel catalysts supported on MgO, CaO, La2O3, ThO2, TiO2, ZrO2 etc. was examined at 0°C. Nickel on MgO was found to give 100 % conversion and almost 100 % selectivity for the formation of N,N-dimethylpropenylamine. It is suggested that nickel catalyst becomes active when supported on basic oxides. The reaction path is discussed on the basis of experiments using deuterium as a tracer.

PDF (204KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1873 - 1877
Published online:
DOI: 10.3987/R-1981-11-1873
Synthesis of Quinoline Alkaloids and Related Compounds. Synthesis of Zanthophylline and a New Synthesis of 3,3-Bis(γ,γ-Dimethylallyl)-N-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline

Pietro Venturella,* Aurora Bellino, and Maria Luisa Marino

*Instituto de Chimica Organica , Facolta de Scienze, Università digli Studi di Palermo, 20 via Archirafi, 90123 Palermo, Italy


The alkaloid zanthophylline (I) was synthesized from the 8-methoxyflindersine (III) by N-alkylation with chloromethylacetate. The 3,3-bis(γ,γ-dimethylallyl)-N-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline (II) was also synthesized by direct methylation of (V).

PDF (131KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1879 - 1882
Published online:
DOI: 10.3987/R-1981-11-1879
On Cardioactive Steroids V. Synthesis of the Pyridone Analogue of Bufalin

Min-Jen Shiao, Thomas Y. R. Tsai, and Karel Wiesner*

*Natural Products Research Center, Department of Chemistry, University of New Brunswick, Bag Service #45222, Fredericton, New Brunswick, E3b 5A3, Canada


An efficient and simple synthesis of azabufalin (2) from compound (4) derived from testosterone is reported.

PDF (76KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1883 - 1887
Published online:
DOI: 10.3987/R-1981-11-1883
Reduction of 1-Substituted 3-Oxidopyridiniums

William R. Ashcroft and John A. Joule*

*Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, U.K.


1-Substituted 3-oxidopyridiniums are smoothly reduced by sodium borohydride in ethanol to give 1-substituted 3-hydroxypiperidines but much less efficiently by lithium aluminium hydride in hot tetrahydrofuran to give mainly, 1-substituted 5-hydroxypiperid-3-eines.

PDF (99KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1889 - 1892
Published online:
DOI: 10.3987/R-1981-11-1889
Novel Syntheses of Dihydrooxazines, Tetrahydropyrimidines and Tetrahydropyridines from Allenyl Nitriles

Stephen R. Landor,* Phyllis D. Landor, Z. Tanee Fomum, and J. Tanyi Mbafor

*Department of Chemistry, Mona Campus, , University of the West Indies, Mona, Kingston 7, Jamaica


α-Allenylnitriles give dihydrooxazines and tetrahydropyridines with 3-hydroxypropylamine whereas with 1,3-diaminopropane they afforded tetrahydropyrimidines.

PDF (64KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1893 - 1897
Published online:
DOI: 10.3987/R-1981-11-1893
13C-NMR Shift Increments for 3-Substituted Pyridines

Roger Dommisse, Eddy Freyne, Eddy Esmans, Josef Lepoivre, and Frank Alderweireldt*

*Labratory of Organic Chemistry, University of Antwerp (RUCA), Groenenborgerlaan 171, B-2020 Antwerp, Belgium


The 13C-NMR spectra of some 3-substituted and 3,5-disubstituted pyridines are examined. It appears that the shift increments for the 3-acetyl group previously published in the literature were based on a wrong assignment of the spectra. A new set of shift increments for 3- or 5-substituents are derived from the spectra of such compounds, most of which were not described before.

PDF (76KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1899 - 1900
Published online:
DOI: 10.3987/R-1981-11-1899
Synthesis of Cannabichromanone

Laura Chiodini, Mauro Di Ciommo, and Lucio Merlini*

*Istituo di Biochimica Generale, Università digli Studi di Milano, Via Venezian 21, 20133 Milano, Italy


The synthesis of the cannabis constituent cannabichromanone is reported.

PDF (67KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1901 - 1905
Published online:
DOI: 10.3987/R-1981-11-1901
Asymmetric Transformation of 2-Chloroalkanoic Acids via Oxazoline Derivatives

Saizo Shibata,* Hajime Matsushita, Hajime Kaneko, Masao Noguchi, Masahiko Saburi, and Sadao Yoshikawa

*Central Reseasrch Institute, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227-8512, Japan


Asymmetric transformation of 2-chloroalkanoic acids via oxazoline derivatives were examined using (S)-phenylalaninol as a chiral auxiliary. After the transformation optical purities of the acids were appreciably improved compared with those of the acids obtained before the transformation.

PDF (104KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1907 - 1912
Published online:
DOI: 10.3987/R-1981-11-1907
How Regioselective Are 1,3-Dipolar Cycloadditions with Carbonyl Ylides?

Jürgen Brokatzky-Geiger and Wolfgang Eberbach*

*Chemusches Laboratorium, Universität Freiburg, Albertstr. 21, D-7800 Freiburg, Germany


Several cycloaddition reactions of asymmetrically substituted carbonyl ylides are described.

PDF (134KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1913 - 1917
Published online:
DOI: 10.3987/R-1981-11-1913
Tetrahydropyridines in the Prins Reaction: A Novel 3-Oxa-7-azabicyclo[3.3.1]nonane Derivative

Alan Casy* and Francis Ogungbamila

*School of Pharmacy and Pharmacology, University of Bath, Bath, BA2 7AY, U.K.


Reaction of tetrahydropyridines obtained by the dehydration of a diastereoisomeric mixture of 1-benzyl-3,4-dimethyl-4-piperidinols with excess of aqueous formaldehyde and sulphuric acid (Prins reaction) gave 7-benzyl-1,9-dimethyl-9-hydroxy-3-oxa-7-azabicyclo[3.3.1]nonane. The stereochemistry of the bicyclic product (cis N/9-OH, piperidine boat-chair) and of the precursor 4-piperidinols is established from nmr (13C and 1H) and ir spectroscopic evidence.

PDF (138KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1919 - 1921
Published online:
DOI: 10.3987/R-1981-11-1919
Synthesis of Optically Active 6α-Methoxy Penem

Maurizio Foglio, Giovanni Franceschi,* Cosimo Scarafile, and Pierangelo Zini

*Ricerca&Sviluppo Chimico, Farmitalia Carlo Erba SpA, Via dei Gracchi 35, 20146 Milano, Italy


Synthesis of 6α-methoxy-2-acetoxymethyl-2-penem-3-carboxylic acid starting from penicillin V is described.

PDF (83KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1923 - 1926
Published online:
DOI: 10.3987/R-1981-11-1923
An New Photochemical Synthetic Route to 2,3-Benzodiazepines from Isoquinoline N-Imides

Michiko Enkaku, Jyoji Kurita, and Takashi Tsuchiya*

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Photolysis of the isoquinoline N-imides (6) under a basic condition gave the corresponding 5H-2,3-benzodiazepines (7), which were converted to the 3-acetyl-3H-2,3-benzodiazepines (11) by treatment with acetic anhydride.

PDF (88KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1927 - 1932
Published online:
DOI: 10.3987/R-1981-11-1927
Utilization of Sulfoxides Containing Pyridine Nuclei as Phase Transfer Catalysis: III

Naomichi Furukawa, Satoshi Ogawa, Tsutomu Kawai, Keiko Kishimoto, Hisashi Fujihara, and Shigeru Oae*

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


Several sulfoxides bound to pyridine were prepared. These sulfoxides were found to promote nucleophilic substitution reactions of alkyl halides markedly in solid-liquid biphase system.

PDF (118KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1933 - 1936
Published online:
DOI: 10.3987/R-1981-11-1933
Novel Rearrangement of 8H-Isoquino[2,1-b][2]benzazocines to 3-Phenylpyrrolo[2,1-a]isoquinolines and Related Compounds

Miyoji Hanaoka,* Akimori Wada, Yasuhiko Sakamoto, Michie Ichihara, Shingo Yasuda, and Takeshi Imanishi

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


The 8H-isoquino[2,1-b][2]benzazocines (1) were efficiently transformed to the 3-phenylpyrrolo[2,1-a]isoquinolines (3) and related compounds by transannular reactions.

PDF (99KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1937 - 1946
Published online:
DOI: 10.3987/R-1981-11-1937
Studies on the Syntheses of Heterocyclic and Natural Compounds. Part 949. A Total Synthesis of (±)-Corynantheidol

Tetsuji Kametani,* Naoaki Kanaya, Toshio Honda, and Masataka Ihara

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


A facile synthesis of (±)-corynantheidol (17) has been achieved by the application of enamine annelation using 3,4-dihydro-1-methyl-β-carboline (5) and dimethyl 3-methoxyallylidenemalonate (6). Stereochemical assignment for catalytic hydrogenation products of the corresponding enamides has also been investigated.

PDF (236KB)
Communication | Regular issue | Vol 16, No. 11, 1981, pp. 1947 - 1950
Published online:
DOI: 10.3987/R-1981-11-1947
Alternative Syntheses of (±)-Epi- and (±)-Desethyl-ibogamine Using a Diels-Alder Reaction of 1-Benzyl-2(1H)-pyridone

Hiroshi Tomisawa,* Hiroshi Hongo, Hideki Kato, Kumi Sato, and Reiko Fujita

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


The Diels-Alder reaction of 1-benzyl-2(1H)-pyridone (1) with methyl acrylate (2) gave methyl 2-benzyl-3-oxo-2-azabicyclo[2.2.2]oct-7-ene-6-endo-carboxylate (3) as a main product. Using this compound a short total synthesis of (±)-epi-ibogamine was achieved. (±)-Desethylibogamine was also synthesized formally from the Diels-Alder adduct (11) of 1 with maleic anhydride.

PDF (83KB)
Report | Regular issue | Vol 16, No. 11, 1981, pp. 1951 - 1954
Published online:
DOI: 10.3987/R-1981-11-1951
On the Reaction of Ethylene Oxide with cAMP

József Béres,* Ernö Moravcsik, and Lajos Radics

*NMR Laboratory, Central Research Institute of Chemistry, H-1525, Budapest, Hungary


Contrary to recent suggestions, proton coupled carbon-13 spectra show that the title reaction occurs on N1 of the base rather than on the phosphate diester group.

PDF (100KB)
Report | Regular issue | Vol 16, No. 11, 1981, pp. 1955 - 1962
Published online:
DOI: 10.3987/R-1981-11-1955
Studies of Potential Heterocyclic Sulfones as Antimicrobial Agents. Synthesis and Antimicrobial Activity of Some Novel Substituted Arylsulfonylbenzo[h]quinoline Derivatives

Rajendra Prasad Bahuguna, Yogesh Chandra Joshi, Mahaveer Prasad Dobhal, Bhuwan Chandra Joshi,* and Hari Narain Mangal

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


A series of substituted arylthiobenzo[h]quinoline (sulfides, Ia~If and IIa~IIc) synthesised earlier were oxidised (with 1% KMnO4) to get their corresponding sulfones (IA~IF and IIA~IIC). All these compounds have been characterised by their elemental analysis, molecular weight determination (Rast Method) and spectral studies (IR and 1H NMR). These compounds have been screened for antimicrobial activity against Gram positive Cocci and Gram negative Bacilli.

PDF (148KB)
Report | Regular issue | Vol 16, No. 11, 1981, pp. 1963 - 1974
Published online:
DOI: 10.3987/R-1981-11-1963
Photochemical Reaction of 2-Bromo-3-methoxy-1,4-naphthoquinone with Sily Enol Ether — One-pot Synthesis of Polycyclic Aromatic Compounds

Kazuhiro Maruyama,* Seiji Tai, Masahiro Tojo, and Tetsuo Otsuki

*Department of Chemistry, Faculty of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan


5-Hydroxybenz[a]anthracene, 2-aryl-2,6-dihydroxy-5-fomyl-2,3-dihydronaphtho[1,2-b][1,4]dioxin, and 4-arylnaphtho[2,3-d][1,3]dioxepin derivatives were synthesized by one-pot photochemical reaction of 2-bromo-3-methoxy-1,4-naphthoquinone with trialkylsilylenolether.

PDF (315KB)
Report | Regular issue | Vol 16, No. 11, 1981, pp. 1975 - 1985
Published online:
DOI: 10.3987/R-1981-11-1975
Furanomycin Analogs: Optically Active Norfuranomycins

Hosein R. Divanfard, Zenon Lysenko, J. Edward Semple, Pen-Chung Wang, Madeleine M. Joullié,* and John F. Blount

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.


The total synthesis of the four stereoisomeric forms of norfurnanomycin is described. The absolute stereochemistry of these novel amino acids was established by X-ray crystallography.

PDF (182KB)
Report | Regular issue | Vol 16, No. 11, 1981, pp. 1987 - 1992
Published online:
DOI: 10.3987/R-1981-11-1987
Synthesis of 5-Hydroxy-3-methyl-3-pyrrolin-2-one [(±)-Jatropham, an Antitumor Alkaloid] and Its 4-Methyl Isomer

Tatsuo Nagasaka,* Sayuri Esumi, Naganori Ozawa, Yoshiyuki Kosugi, and Fumiko Hamaguchi

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


5-Hydroxy-3-methyl-3-pyrrolin-2-one (1), which is known as jatropham; an antitumor alkaloid, is conveniently synthesized from succinimide. One step synthesis of 5-hydroxy-4-methyl-3-pyrrolin-2-one (2) by the regioselective reduction of methylmaleimide with NaBH4/H+ is also described.

PDF (162KB)
Report | Regular issue | Vol 16, No. 11, 1981, pp. 1993 - 1994
Published online:
DOI: 10.3987/R-1981-11-1993
Preparation and Decomposition of 1,4,6-Trisubstituted 3-Nitroso-tetrahydro-2(1H)-pyrimidinones

Choji Kashima,* Akira Katoh, and Yoshimori Omote

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


1,4,6-Trisubstituted tetrahydro-2(1H)-pyrimidinones (1) were treated with sodium nitrite in acidic conditions to afford the corresponding 3-nitroso-2(1H)-pyrimidinones (2) in high yields. The decomposition of 2a with potassium hydroxide was also discussed.

PDF (49KB)
Review | Regular issue | Vol 16, No. 11, 1981, pp. 1995 - 2034
Published online:
DOI: 10.3987/R-1981-11-1995
The Chemistry of 4,5-Dihydro-5-oxo-1,3-oxazoles

Arya K. Mukerjee* and Pradeep Kumar

*Chemistry Department, Faculty of Science, Banaras Hindu University, Varanasi-221 005, India


4,5-Dihydro-5-oxo-1,3-oxazoles are important class of heterocycles and interest in their chemistry continues unabated because of their usefulness as synthons. In this review an attempt has been made to present the chemistry of this class in an integrated form and in proper perspective under the following headings:

PDF (893KB)
25 data found. 1 - 25 listed