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. 24, No. 5, 1986
Published online:
■ Synthesis of Novel Hexahydroquinolines and Hexahydroacridines
Magid Abou-Gharbia*
*Medical Chemistry Section, Wyeth Laboratories, P.O.Box 8299, Philadelphia, Pennsylvania 19101, U.S.A.
Abstract
Novel hexahydroquinolines and hexahydroacridines were prepared as potential antihypertensive agents.
Published online:
■ Synthesis of Protein Complexes of Bis-indole Alkaloids from Catharanthus roseus
Mauri Lounasmaa,* Reija Jokela, Aarre Huhtikangas, Seppo Lapinjoki, Jukka Heiskanen, Timo Lehtola, and Toivo Naaranlahti
*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland
Abstract
Conjugation of vincristine (VCR) 1 and vinblastine (VBL) 2 to proteins through the C-10’ position of the “catharanthine moiety” is described. The procedure was applied to the production of immunogenic complexes of the drugs and bovine serum albumin (BSA), and to the synthesis of an enzyme-linked tracer from VCR 1 and alkaline phosphatase.
Published online:
■ Sensitized Photooxidation of 2-Furfuryl Benzoate in Methanol
Yueh-Hsiung Kuo* and Kae-Shyang Shih
*Department of Chemistry, National Taiwan University, Roosevelt Road Section 4, Taipei 106, Taiwan, R.O.C.
Abstract
Sensitized photooxidation of 2-furfuryl benzoate in methanol gave eight products. The mechanism for their formations are discussed.
Published online:
■ Studies on the Synthesis of Heterocyclic Compounds. Part XI. A Novel Access to Some 2-Substituted 4(3H)-Quinazolinones
Maria Luisa Bajardi, Giuseppe Daidone, Domentrio Raffa, and Salvatore Plescia*
*Instituto di Chimica Farmaceutica e Tossicologica, Università digli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy
Abstract
Hydrogenolysis of N-(3-R-4-R’-isoxazol-5-yl)-2-nitrobenzamides 1a,b,c with iron powder in acetic acid afforded directly the 2-substituted 4(3H)-quinazolinones 5a,b,c. Additionally, the structure of the methylation product of 2-acetonyl-4(3H)-quinazolinone is elucidated. An attempt devoted to achieve an alternative synthesis of compound 6a by reaction of anthranilamide with ethyl acetoacetate failed to give the desired benzodiazocine but only 2-methyl-4(3H)-quinazolinone 7a was obtained. Products 5a and 9 were evaluated for their antimicrobial activity.
Published online:
■ An Easy Route to a Chiral Diol in the Furan Series from 2-Deoxyaldohexoses
Catharine Fayet and Jacques Gelas*
*Ecole National Supérieure de Chimie de Clermont-Ferrand, BP45, 63170 Aubière, France
Abstract
A preparative access to a furan substituted by a chiral 1,2-dihydroxyethyl group at position 2 is described. The very simple procedure uses the dehydration of 2-deoxyaldohexoses by heating the sugar with anhydrous pyridinium chloride. This reaction allows comments about general mechanism of dehydration of sugars to furan.
Published online:
■ Nuclear Transformations by Hydrogenolysis: Synthesis of Pyrimidinones from Isoxazoles Derivatives
Sergio Caronna, Onofrio Migliara, and Salvatore Petruso*
*Tecnologie Farmaceutiche, Dipartimento di Chimica, Università digli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy
Abstract
Pyrimidinones derivatives are obtained by catalytic hydrogenation of the products resulting from the condensation of 3,5-dimethylisoxazole-4-carboxylic acid chloride with urea (or benzamidine).
Published online:
■ Structure of Mulberrofuran P, a Novel 2-Arylbenzofuran Derivative from the Cultivated Mulberry Tree (Morus alba L.)
Yoshio Hano and Taro Nomura*
*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan
Abstract
A novel 2-arylbenzofuran derivative, mulberrofuran P, was isolated from an acetone extract of the reddish violet powder obtained from the surface of the root bark of cultivated mulberry tree (Ichinose, a cultivated variety of Morus alba L.). Its structure was shown to be 1 on the basis of spectral evidence. Mulberrofuran P is regarded biogenetically as a variation of a Diels-Alder type adduct of a chalcone derivative and a dehydroprenyl-2-arylbenzofuran derivative.
Published online:
■ Formation of an Unexpected Product, a Functionalized Dioxane, under Aprotic Acetalization Conditions
Jack Chiarello, Shin-Yih Chen, and Madeleine M. Joullié*
*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.
Abstract
The formation of a substituted dioxane under aprotic acetalization conditions is observed.
Published online:
■ Heterocyclic Spiro Compounds. II. Synthesis of 1’-Substituted 1,3,4,6,7,11b-Hexahydrospiro[benzo[a]quinolizine-2,3’-pyrrolidine]-2’,5’-diones
J. Carlos Menéndez, Gregorio G. Trigo, and Mónica M. Söllhuber*
*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain
Abstract
The synthesis of 1’-substituted derivatives of 1,3,4,6,7,11b-hexahydrospiro[benzo[a]quinolizine-2,3’-pyrrolidine]-2’,5’-dione is achieved starting from a suitable cyanohydrin 4 and ethyl sodiocyanoacetate, according to reaction Scheme 1. The structure of the intermediate of the cyclization reaction that leads to the target compounds 2 is described.
Published online:
■ A Convenient Synthesis of 4-Oxo-4H-quinolizines
Luciana Forti, Maris Luisa Gelmi, Donato Pocar, and Marinella Varallo*
*Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi di Milano, Via Venezian 21, I-20133 Milano, Italy
Abstract
By reacting α-substituted picolines (1) (or their synthetic equivalents) with β,β-dichlaroprapenals (4) (or their synthetic equivalents) substituted 1-(2-pyridyl)-4,4-dichloro-1,3-butadienes (6) were produced. Compounds (6) were smoothly cyclized to the corresponding 4-oxo-4H-quinolizines (8) bearing substituents in the 1 and/or 3 positions.
Published online:
■ On the Reaction of 1-Ethoxycarbonyl-1H-1,2-diazepine with Molybdenum and Iron Carbonyl Complxes
Makoto Nitta* and Hiroyuki Miyano
*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan
Abstract
The reaction of 1-ethoxycarbonyl-1H-1,2-diazepine (3) with [Mo(CO)3 (MeCN)3] resulted in the N-N bond cleavage of the seven-membered ring to give dienaminocarboxaldehyde 4 and dienaminonitriles, 5 and 6. On the other hand, the reaction of 3 with [Fe2 (CO)9] or with [Fe(CO)5] afforded 4 and 6, or 2-(ethoxycarbonylamino)pyridine and N,N’-di(2-pyridyl)urea, in addition to [diene]-Fe(CO)3 complex.
Published online:
■ Preparation of New 4,4’-Linked Bis-acridines, 9,9’-Linked Bis-acridines and 4,4’-9,9’ Bi-linked Bis-acridines
Richard Vidal, Jean Pierre Galy,* Emile Jean Vincent, Anne Marie Galy, and Jacques Barbe
*Laboratoire de Chimie Organique Physique, Facluté des Sciences et Techniques de Saint Jérôme, Université d‘Aix-Marseille III, Avenue Escardille Normandie Niemen (Case 552), 13397 Marseille Cedex 13, France
Abstract
New bis-derivatives belonging to the acridine series have been prepared. These compounds are bis(4-amino-9-acridanones) and bis(4-amino-9-thioacridanones) linked in positions 4,4’ or 9.9’. There are also some 4,4’-diaminoacyl-9,9’-dithioalkyl bi-linked bis-acridines. In any case, chemical structures are discussed with reference to the 13C NMR chemical shifts, as well as to the HSAB concept.
Published online:
■ A Laboratory Synthesis of 4-Hydroxy-2(5H)-furanone (β-Tetronic Acid)
Takefumi Momose,* Naoki Toyooka, and Yumi Takeuchi
*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan
Abstract
A ‘one pot’-fashioned preparation of 4-hydroxy-2(5H)-furanone (β-tetronic acid) was conducted in 38-40% overall yield starting from ethyl acetoacetate.
Published online:
■ Dihydropyrimidines: Synthesis, Structure and Tautomerism
Alexander L. Weis* and Henk C. van der Plas
*Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel
Abstract
This review describes the preparation of the dihydropyrimidines, the structure, stability and tautomerism of these systems and the rearrangements in which these compounds can be involved.