Regular Issue

Vol. 24, No. 5, 1986

44 data found. 31 - 44 listedFirst Previous
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1347-1353
Published online:
DOI: 10.3987/R-1986-05-1347
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.

PDF (116KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1355-1360
Published online:
DOI: 10.3987/R-1986-05-1355
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.

PDF (125KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1361-1366
Published online:
DOI: 10.3987/R-1986-05-1361
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.

PDF (129KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1367-1372
Published online:
DOI: 10.3987/R-1986-05-1367
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.

PDF (155KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1373-1376
Published online:
DOI: 10.3987/R-1986-05-1373
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.

PDF (95KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1377-1380
Published online:
DOI: 10.3987/R-1986-05-1377
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).

PDF (85KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1381-1386
Published online:
DOI: 10.3987/R-1986-05-1381
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.

PDF (126KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1387-1391
Published online:
DOI: 10.3987/R-1986-05-1387
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.

PDF (129KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1393-1399
Published online:
DOI: 10.3987/R-1986-05-1393
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.

PDF (165KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1401-1410
Published online:
DOI: 10.3987/R-1986-05-1401
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.

PDF (233KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1411-1418
Published online:
DOI: 10.3987/R-1986-05-1411
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.

PDF (201KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1419-1427
Published online:
DOI: 10.3987/R-1986-05-1419
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.

PDF (206KB)
Paper | Regular issue | Vol 24, No. 5, 1986, pp.1429-1431
Published online:
DOI: 10.3987/R-1986-05-1429
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.

PDF (77KB)
Review | Regular issue | Vol 24, No. 5, 1986, pp.1433-1455
Published online:
DOI: 10.3987/R-1986-05-1433
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.

PDF (514KB)
44 data found. 31 - 44 listedFirst Previous