HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 23, No. 12, 1985
Published online:
■ The Isolation and Structure of Ervaticine, a New Indole Alkaloid from Ervatamia coronaria
Atta-ur-Rahman* and Anjun Muzaffar
*H. E. J. Postgraduate Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan
Abstract
A new 2-acylindole alkaloid “ervaticine” was isolated from the leaves of Ervatamia coronaria and its structure was determined as (I) on the basis of spectral studies.
Published online:
■ Nevadenine and Nevadensine, Two New Diterpenoid Alkaloids from Aconitum nevadense Vechtr.
Antonio G. González,* Gabriel de la Fuente, Tomás Orribo, and Rafael Díaz Acosta
*Instituto de QUímica Orgánica, Instituto de Productos Naturales Orgánicos, C. S. I. C./ Unversidad de La Laguna, La Laguna, Tenerife, Canary Islands, Spain
Abstract
Neoline, chasmanine, isotalatizidine, and two new C-19 diterpenoid alkaloids, nevadenine and nevadensine, were isolated from Aconitum nevadense. The structures of the new bases were established by 1H and 13C-nmr spectroscopy, and chemical derivation to known alkaloids.
Published online:
■ Nitroles in Heterocyclic Synthesis: New Routes for Synthesis of Pyran, Pyridine and Pyrrole Derivatives
Galal A. M. Nawwar,* Saad A. Osman, Khairy A. M. El-Bayouki, Galal E. H. Elgemeie, and Mohamed H. Elnagdi
*Natural Products Department, National Research Centre, Dokki, Cairo, Egypt
Abstract
Synthesis of pyran, pyridine and pyrrole derivatives utilising cinnamoylacetonitrile as starting component is reported.
Published online:
■ New Boron Heteropentacyclic Compounds of C2 Symmetry Bearing Two Chiral Atoms: Nitrogen and Boron
Nerberto Farfán and Rosalinda Contreras*
*Centro de Investigación y de Estudios Avanzados, Departmento de Química , I.P.N, Apartado 14-740, México, D.F., 07000, Mexico
Abstract
The preparation and spectroscopic characterization of two new boron heteropentacyclic compounds derived from 2,5-diaminohydroquinone ephedrines is described. Although the nitrogen boron coordination affords four new chiral centers, stereoselective ring closure proceeds to give only one isomer.
Published online:
■ Synthesis of a 2,6-Dithia-6b,8c-diazadicyclopent[ef,kl]s-indacene as a Pentacyclic 16π Heteroannulene of Bis Nitrogen-Bridged Type
Shoji Kajigaeshi, Yoichi Kawano, Shizuo Fujisaki, and Shuji Kanemasa*
*Instituete of Advanced Material Study, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan
Abstract
As a new 16Π heteroannulene with two nitrogen bridges, a 2,6-dithia-6b,8c-diazadicyclopent[ef,kl]s-indacene was synthesized through the repeated acetic anhydride cyclizations of 3,8-dimethyl-5,10-dihydrodithiazolo[3,4-a,3’,4’-d]pyrazine-4,9-diium salts, the dimer of 4-halomethyl-2-methylthiazoles.
Published online:
■ Witting Reaction of Azabicyclo-ketones in Various Two-phase Systems
Gregorio G. Trigo and Emilio F. Llama*
*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain
Abstract
The present study is concerned with a comparison of variants of the phase transfer catalytic (PTC) Wittig reaction performed over azabicyclo-ketone systems, in attemt to extend the scope of the reaction and to learn whether an additional catalyst is required.
Published online:
■ Idenfication of Isomeric 2-Dialkylaminoethylthio-thieno[2,3-c] and [3,2-d]Isothiazoles with Antifungine Activity by Electron Impact Mass Spectrometry
Pasquale Agozzino,* Ennio Bousquet, Leopoldo Ceraulo, and Giuseppe Romeo
*Instituto di Chimica Farmaceutica e Tossicologica, Università digli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy
Abstract
The EI mass spectra of sixteen title compounds were studied. The 5-acyl and the 2-dialkylaminoethylthio substituents are responsible of the main fragmentation processes of thieno[2,3-c] and thieno[3,2-d]isothiazoles. An easy criterion of distinction between the two types of heterocyclic compounds results from the comparison of the relative abundances of some ionic species.
Published online:
■ A New Spremidine Alkaloid from Capparis decidua
Viqar Uddin Ahmad,* Shoib Arif, Aziz-ur-Rahman Amber, Khan Usmanghani, and Ghulam Abbas Miana
*H. E. J. Postgraduate Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan
Abstract
A new spermidine alkaloid, named capparidisine, has been isolated from the root bark of Capparis decidua and its structure was eluciated by spectral studies.
Published online:
■ Reaction of Diimide-diacids Trimellitimide Derivatives with 1-Chloro-2,3-epoxypropane
Pedro-Alberto Martínez, Virginia Cádiz,* Angels Serra, and Ana Mantecón
*Departamento de Química Orgánica, Facultad de Química de Tarragona, Universidad de Barcelona, Pl. Imperial Tarraco s/n, Tarragona, Spain
Abstract
The synthesis of various esters containing imide and oxirane cycles has been improved from potassium salts of several diimide-diacids instead of their free carboxylic diacids using 1-chloro-2,3-epoxypropane in excess and a quaternary ammonium halide as catalyst. The spectral data and physical and chemical characteristics were discussed.
Published online:
■ Approaches to the Total Synthesis of the Montanine (Amaryllidaceae) Alkaloids. Preparatiion of Isomeric 3-Aryloctahydroindoles
Ignacio H. Sánchez,* María Isabel Larraza, Irma Rojas, Francisco Breña, Humberto J. Flores, and Krzysztof Jankowski
*Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitatria, Coyoacán 04510, Mexico
Abstract
The preparation of various isomeric 3-aryloctahydroindoles, potential synthons for the total synthesis of the montanine-like Amaryllidaceae alkaloids, is described.
Published online:
■ A New Synthesis of 2-Imidazolones
Pen-Chung Wang*
*Designed Latexes and Resins Research, Michigan Division, 1604 Building, The Dow Chemical Company, Midland, MI 48640, U.S.A.
Abstract
2-Imidazolones were synthesized from ethylene ureas utilizing anodic oxidation as the key step.
Published online:
■ Electrophilic Substitution of Indoles: Part 7 — Application of HOMCOR (COSY) - 2D NMR Sprectoroscopy in Structure Elucidation
Julie Banerji,* Munmun Saha (née Kumar), and James N. Schoolery
*Chemistry Department, University College of Science, 92 Acharya Prafulla Chandra Road, Calcutta-700009, India
Abstract
The electrophilic substitution of 2-methylindole with acetone in the presence of BF3·Et2O has been discussed and the application of the HOMCOR (COSY) 2D NMR spectroscopy in settling the structure of the product.
Published online:
■ Transformation of Phenylchlorodiazirines to 1,3-Dioxolanes and a 1,3-Dithiolane
Michael T. H. Liu* and Joseph Kokosi
*Department of Chemistry, University of Prince Edward Island, Charlottetown, Prince Edward Island, C1A 4P3, Canada
Abstract
Chlorophenylcarbene reacts with bifunctional or polyfunctional alcohols and ethanedithiol to form 2-phenyl-1,3-dioxalanes and 2-phenyl-1,3-dithiolane.
Published online:
■ 11-Nor-4,9-anhydrotetrodotoxin-6,6-diol: A Synthon for Tetrodotoxin Analogs
Ronald J. Nachman and Harry S. Mosher*
*Department of Chemistry, Stanford University, 735 Dolores Street, Stanford, CA 94305-5080, U.S.A.
Abstract
Tetrodotoxin (1), the sodium channel-blocking agent, is converted to non-toxic 4,9-anhydrotetrodotoxin (4), which is oxidized to 11-nor-4,9-anhydrotetrodotoxin-6,6-diol (5). This inactive derivative can be hydrolyzed to pharmacologically active 11-nortetrodotoxin-6,6-diol (3). Preliminary studies have been made with the title compound to determine its suitability for the preparation of tetrodotoxin analogs.
Published online:
■ Application of Furan Oxidations in Synthesis: Total Synthesis of (±)-Coriolic Acid
Bruce P. Gunn*
*Pharmaceutical Product Division, Abbott Laboratories, D-47B, AP 10, 100 Abbott Park Road, Abbott Park, Illinois 60064-3500, U.S.A.
Abstract
As a general synthetic approach to compounds containing the cis-trans allylhydroxy functionality (subunit A), an appropriately substituted furan nucleus is oxidatively cleaved to provide an unsaturated 1,4-dicarbonyl moiety suitably disposed for further elaboration. The total synthesis of (±)-coriolic acid demonstrates the utility of the approach.
Published online:
■ Synthetic Studies of 1-Azapenem
Tomoyuki Shibata, Yukio Sugimura,* Sadao Sato, and Kayoko Kawazoe
*Research Institute, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan
Abstract
Total synthesis of 1-azapenem (5) is reported. The key intermediate 24 was synthesized by the intramolecular cyclization of 17 and subsequent desilylation. Alkylation of 24 and subsequent hydrogenolysis gave 5.
Published online:
■ A Direct Conversion of Phenanthrenes to Aporphinoids
Julio A. Seijas, Angel Rodríguez de Lera, Carmen Villaverde, and Luis Castedo*
*Facultad de Química y Sección de Alcaloides, Deparamento de Química Orgánica, C. S. I. C., Santiago de Compostela, Spain
Abstract
We describe a single-step conversion of phenanthrene alkaloid derivatives into oxoaporphines based on the cyclization of 9,10-phenanthrenediones with ethanamine side-chains under basic conditions.
Published online:
■ Transformation from Aporphine X-Oxides to 1-(N-Methyl-N-hydroxylaminoethyl)phenanthrene Derivatives
Sheng-Teh Lu* and Yang-Chang Wu
*School of Pharmacy, Kaohsiung Medical College, 100 Shih Chuen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.
Abstract
Neat treatment of aporphine N-oxides prepared by the m-chloroperbenzoic acid (m-CPBA) oxidation of aporphines afforded 1-(N-methyl-N-hydroxylaminoethyl)phenanthrene derivatives which were characterized by the physical and chemical evidences. The biogenetic pathway from aporphines to phenanthrenes is also discussed.
Published online:
■ Saturated Heterocycles. 93. Facile Dehydrogenation and an Unexpected Catalytic Hydrogen Transfer Reaction of 1,2,5,6,7,8-Hexahydroquinazolin-4(3H)-ones
Ferenc Fülöp and Gábor Bernáth*
*Institute of Pharmaceutical Chemistry, University Medical School, Szeged, Hungary
Abstract
2-Phenyl-1,2,5,6,7,8-hexahydroquinazolin-4(3H)-one (2) and the related 2-(3’-cyclohexenyl) derivative (4) were observed to undergo a facile dehydrogenation and an intermolecular catalytic hydrogen transfer in the presence of Pd/C, even in a hydrogen atmosphere.
Published online:
■ Novel Rearrangement of a 3-Amino-1,3-thiazole-2-thione
Alan R. Katritzky* and Shibli Bayyuk
*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, U.S.A.
Abstract
Some new derivatives of 3-amino- and 3-phenylamino-4-phenyl-1,3-thiazole-2-thione have been prepared and characterized. When 3-(N-phenylbenzamido)-4-phenyl-1,3-thiazole-2-thione in rearranged thermally it gives 3-(2-benzoylphenylamino)-4-phenyl-1,3-thiazole-2-thione and 4-[4-(N-phenylbenzamido)phenyl]-1,3-thiazole-2-thione.
Published online:
■ A Novel Synthesis of 4-H-Thiopyrans: Unexpected Products of Reaction of Cyanothioacetamide with Cinnamonitrile Derivatives
Galal Eldin Hamza Elgemeie,* Mohamed Mohamed Mohamed Sallam, Sherif Mourad Sherif, and Mohamed Hilmy Elnagdi
*Chemistry Department, Faculty of Science, Minia University, Minia, Egypt
Abstract
The reaction of arylidenemalononitrile with cyanothioacetamide afforded either thiopyrans or pyridine derivatives depending on reaction conditions. 13C NMR was utilised to elucidate the proposed structures of the reaction products.
Published online:
■ Structure of Solaparnaine, a New Spirosolane Alkaloid from the Green Berries of Solanum asperum Vahl
Jnanabrata Bhattacharyya*
*Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraiba, 58051-970 João Pessoa, PB, Brazil
Abstract
The structure of a new spirosolane alkaloid, solaparnaine, isolated from the green berries of Solanum asperum Vahl as an aglycone has been determined mainly with the aid of 13C NMR spectroscopy and MS.
Published online:
■ Syntheses of 7-Substituted Indoles
Masanori Somei* and Yoshihiro Saida
*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan
Abstract
A facile synthetic method for 7-iodoindole was established. Its versatility for the syntheses of 7-substituted indoles was shown by leading it to 7-methoxyindole and methyl 3-(indol-7-yl)acrylate.
Published online:
■ Hydrogenation of Biopterin and Its Analogues: Application for the Convenient Procedure of Biopterin Cafactor and Related 5,6,7,8-tetrahydropterins
Sadao Matsuura,* Shizuaki Murata, and Takashi Sugimoto
*Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan
Abstract
A large scale and stereoselective hydrogenation of biopterin to (6R)-5,6,7,8-tetrahydrobiopterin was developed. The procedure was applied for various hydroxyalkylpterins such as neopterin [(1’S,2’R)-6-(1’,2’,3’-trihydroxypropyl)pterin] and diastereomers of biopterin.
Published online:
■ Recent Developments in the Synthesis of Pyrazole Derivatives
Mohamed Hilmy Elnagdi, Galal Eldin Hamza Elgemeie,* and Fatma Abd-Elmaksoud Abd-Ellal
*Chemistry Department, Faculty of Science, Minia University, Minia, Egypt
Abstract
The recently reported approaches for synthesis of pyrazoles are surveyed. Reactions of theoretical or practical importance are discussed in some detail.