Regular Issue

Vol. 41, No. 7, 1995

15 data found. 1 - 15 listed
Communication | Regular issue | Vol 41, No. 7, 1995, pp. 1381 - 1384
Published online:
DOI: 10.3987/COM-95-7089
Dimerization of Norisoacronycine

Shinji Funayama, Tomoko Aoyagi, Kaori Tadauchi, Tzu-Yun Pan, Shigeo Nozoe*, and Geoffrey A. Cordell

*Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980, Japan


A new type of acridone dimer with a C-C junction between the prenyl moieties was obtained by treating norisoacronycine under acidic conditions. The chemical structure was deduced mainly by the comparison of its nmr spectral data with those of the acridone dimers which had been prepared previously.

PDF (104KB)
Communication | Regular issue | Vol 41, No. 7, 1995, pp. 1385 - 1388
Published online:
DOI: 10.3987/COM-95-7095
A Concise Approach to Antifertility Agents; Structural Analogues of Yuehchukene

Minoru Ishikura*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-02, Japan


Palladium catalyzed carbonylative cross-coupling reaction using lithium triethyl(1-methylindol-2-yl)borate (1) was applied in a concise formation of structural analogues of yuehchukene.

PDF (91KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1389 - 1397
Published online:
DOI: 10.3987/COM-94-6916
Synthesis and Antibacterial Activity of 1-Cyclopropyl-6,8-difluoro-7-(2-substituted 4,6-dihydro-1H-pyrrolo[3,4-d]thiazol-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

Wan-Joo Kim*, Bong-Jin Kim, Tae-Suk Lee, Keun-Soo Nam, and Keun-Jae Kim**

*Korea Research Institute of Chemical Technology, Pharmaceutical Division, P.O. box 107, Yu-Sung ku, Taejon, Korea 305-606


Quinolone derivatives (9 and 10) substituted with bicyclothiazole (7) and (8) at C-7 position were synthesized. Bicyclothiazole derivatives (7 and 8) were prepared through 9 steps by way of the 4-bromo-3-oxopyrrolidine (16) was a key intermediate and introduced into the title compounds as new C-7 substituents. In vitro antibacterial activity of 9 and 10 was also reported.

PDF (263KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1399 - 1419
Published online:
DOI: 10.3987/COM-94-6941
Simultaneous Conversion of N(1)-(2-Aminoethyl)adenosine to N6-(2-Aminoethyl)adenosine and Tricyclic 1. N6-Ethanoadenosine under Mild Aqueous Conditions

Andreas F. Bückmann,* Victor Wray, and Henk C. van der Plas

*Department of Enzymology, GBF, Gesellschaft für Biotechnologische Forschung mbH, Mascheroder Weg 1, D-38124 Braunschweig, Germany


Under mild aqueous conditions (50 °C, pH range 6 - 7) N(1)-(2AE)-adenosine (2) can be converted to N6-(2AE)-adenosine (7) by Dimroth rearrangement at unexpectedly high rate. In a parallel reaction tricyclic 1,N6-ethanoadenosine (6) is formed. The latter reaction is new in heterocyclic organic chemistry and is strongly catalysed by the monoanions of phosphoric and arsenic acid and, less strongly, by the acetate anion.

PDF (462KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1421 - 1424
Published online:
DOI: 10.3987/COM-94-7019
Design and Synthesis of Imidazolium Cyclophane

Meiming Luo, Shengjin Guo, Chenghe Zhou, and Rugang Xie*

*Department of Chemistry, Sichuan University, Chengdu 610064, P. R. China


1,4-Diimidazol-1-ylbutane (2) was prepared by PTC technique. Treatment of 2 with α,α’-dibromoxylene afforded novel imidazolium cyclophanes (3a,b) in good yields.

PDF (108KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1425 - 1430
Published online:
DOI: 10.3987/COM-94-7022
Alkaloids from the Neutral Fraction of Telitoxicum krukovii

Mary D. Menachery*, Geoffrey W. Blake, Cathleen Beiswenger, and Alan Freyer

*Penn State Altoona, 3000 Ivyside Park, Altoona, Pennsylvania 16601-3760, U.S.A.


Two new aporphinoids N-formyldehydroanonaine (1), telikovinone (2), and the known alkaloids N-demethyl-N-formyldehydronuciferine, N-formylnuciferine, 7-chloro-6-demethylcepharadione B, and norcepharadione B have been isolated and identified from the neutral fraction of Telitoxicum krukovii.

PDF (165KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1431 - 1434
Published online:
DOI: 10.3987/COM-95-7031
Reaction of Pentafluoropyridine and α-Lithiated Arylacetonitriles with n-Butyllithium and Methyllithium in Ether

Edward R. Biehl,* Hala Mohammed Refat, and Amamed A. Fadda

*Department of Chemistry, Southern Methodist University, Dallas, TX 75275, U.S.A.


Treatment of one equivalent each of pentafluoropyridine (6) and n-butyllithium with two equivalents of lithioarylacetonitriles (3) gave α-aryl-4-n-butyl-3,5,6-trifluoro-2-pyridylacetonitrile (9) in good yields (83-85%). Similar treatment of equivalent amounts of 6, 3, and methyllithium gave α-aryl-2,3,5,6-tetrafluoro-4-pyridylacetonitriles (11) also in good yields (79-87%). The introduction of the n-butyl and α-arylacetonitrile groups most likely arise through nucleophilic aromatic substitution pathways.

PDF (126KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1435 - 1444
Published online:
DOI: 10.3987/COM-95-7065
An Efficient Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines by Chiral Binaphthol-Titanium Complex Catalysis

Masayuki Sato,* Satoshi Sunami, Yoshiaki Sugita, and Chikara Kaneko

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


The asymmetric aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dioxines or the 6-ethylidene analogue with achiral aldehydes proceeds in a highly enantioselective manner under chiral binaphthol-titanium complex catalysis to afford 6-substituted 1,3-dioxin-4-ones which serve as chemical equivalents of δ-hydroxy-β-keto esters, potential chiral building blocks. An explanation for the stereoselectivity is also presented.

PDF (259KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1445 - 1459
Published online:
DOI: 10.3987/COM-95-7063
[4+2]Cycloaddition Reactions of 1,4-Bis(trifluoromethyl)pyrido[3,4-d]pyridazine with Indole-Type Dienophiles

Norbert Haider,* Kurt Mereiter, and Richard Wanko

*Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse14, A-1090 Vienna, Austria


[4+2] Cycloaddition reactions of the title compound (1) with electron-rich indole-type dienophiles afford — besides different types of side products — tetracyclic compounds with a pyridocarbazole skeleton, structurally related to the alkaloid ellipticine or its isomer, isoellipticine. Three of the reaction products (compounds 4, 5, and 10) were characterized by X-ray structure determination.

PDF (418KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1461 - 1470
Published online:
DOI: 10.3987/COM-95-7067
Pyridazines, 74. Synthesis of Novel 4,5-Disubstituted Pyridazines by Homolytic Substitution and Structure Determination of Unexpected Reaction Products

Gottfried Heinisch,* Barbara Matuszczak, Kurt Mereiter, and Josef Soder

*Institute of Pharmaceutical Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria


Synthesis of the 5-aryloxymethyl-4-pyridazinecarboxylic acid derivatives (1a-d) and of the analogous thioethers (1e,f) by radical reactions in a two-phase system is reported. The stereochemical assignment of unexpected dimeric reaction products formed in the absence of an organic layer is presented.

PDF (239KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1471 - 1478
Published online:
DOI: 10.3987/COM-95-7070
A Versatile Synthesis of Substituted Indazoles

Jin Il Kim, Byung Chul Kim, Seung Wook Moon, and Yurngdong Jahng*

*College of Pharmacy, Yeungnam University, Kyongsan 712-749, Korea


A four-step synthetic sequence for substituted indazoles was presented from 2-acylcyclohexane-1,3-diones via either simultaneous or stepwise dehydration and dehydrogenation of 4-substituted 4-hydroxy-4,5,6,7-tetrahydroindazoles as a key step.

PDF (236KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1479 - 1490
Published online:
DOI: 10.3987/COM-95-7071
Reactivity of N1-Acylacetamidrazones towards Diethyl Acetylenedicarboxylate: Cyclization to Ethyl Pyrroleacetates and 1-Acylaminopyridones

Angela Maria Bernard, Maria Teresa Cocco,* Cenzo Congiu, Valentina Onnis, and Pier Paolo Piras

*Dipartimento Farmaco Chimico Tecnologico, Via Ospedale n° 72, I-09124 Cagliari, Italy


The reaction between N1-acylacetamidrazones (1) and diethyl acetylenedicarboxylate (2) is described. The nucleophilic addition of the β-carbon atom of 1 on the triple bond affords the non isolable intermediate (3). Depending on the reaction conditions and on the substitution pattern of the amidrazone, 3 gives rise to ethyl 5-(2-acylhydrazino)-4-(ethoxycarbonyl)-2-oxo-2H-pyrrole-3-acetates (4) and / or diethyl 1-acylamino-2-amino-1,6-dihydro-6-oxo-3,4-pyridinedicarboxylates (5).

PDF (267KB)
Paper | Regular issue | Vol 41, No. 7, 1995, pp. 1491 - 1501
Published online:
DOI: 10.3987/COM-95-7082
Heterocyclic Amidines: I. A One-Step Synthesis of New α-Substituted Imidazolylphenylacetic Acids

Carmela Saturnino, Mustapha Abarghaz, Martine Schmitt, Camille-Georges Wermuth, and Jean-Jacques Bourguignon*

*Laboratoire de Pharmacochimie Moléculaire, UPR 421 du CNRS, Centre de Neurochimie, 5 rue Blaise Pascal 67084 Strasbourg Cedex, France


The reaction of α-phenyl-β-formylacrylic derivatives with various amidines (benzamidine, acetamidine) and heterocyclic amidines (2-aminopyridines, 3-aminopyridazines), yields α-substituted imidazolylphenylacetic acids and imidazo[1,2-x]azines bearing a phenylacetic acid residue in position 3. Some mechanistic aspects of the cyclocondensation reaction will be discussed.

PDF (287KB)
Review | Regular issue | Vol 41, No. 7, 1995, pp. 1503 - 1524
Published online:
DOI: 10.3987/REV-93-SR15-1
Optimization of Synthesis of Nitroimidazoles and Nitropyrazoles Based on Polarographic Investigations

Dragica Dumanovic*, Djuro Kosanovic, and Petr Zuman

*ICN Galenika Institute, 29., novembar 111, 11000 Belgrade, Yugoslavia


Direct, simple, fast and inexpensive polarographic method enables selective determinations of nitroimidazoles or nitropyrazoles (nitroazoles) in mixtures which can be used for monitoring synthetic processes and selecting optimal conditions for synthesis.

PDF (367KB)
Review | Regular issue | Vol 41, No. 7, 1995, pp. 1525 - 1574
Published online:
DOI: 10.3987/REV-95-468
Synthesis and Reactions of Lithiated Monocyclic Azoles Containing Two or More Hetero-atoms. Part VI: Triazoles, Tetrazoles, Oxadiazoles, and Thiadiazoles

M. Ross Grimmett and Brian Iddon*

*The Ramage Laboratories, Department of Chemistry and Applied Chemistry, University of Salford, Salford M5 4WT, England


The metallation and halogen → metal exchange reactions of 1,2,3- and 1,2,4-triazoles, tetrazoles, 1,2,3-, 1,2,4-, 1,2,5-, and 1,3,4-oxadiazoles, and 1,2,3-, 1,2,4-, 1,2,5-, and 1,3,4-thiadiazoles and the reactions of the resulting organometallic derivatives, particularly lithiated derivatives, are reviewed comprehensively.

PDF (743KB)
15 data found. 1 - 15 listed