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  • Organic Chemistry  (47)
  • J64
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  • 1
    Electronic Resource
    Electronic Resource
    2,3-Donor-Acceptor-Substituted 1,3-Butadienes. Synthesis by SO2-extrusion from 3-sulfolenes and diels-alder reactions (1994)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 336 (1994), S. 343-349 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The thermal extrusion of SO2 from disubstituted 3-sulfolenes 3 leads to 2,3-donor-acceptor-substituted 1,3-butadienes 4. These dienes react with acrylic acid ester and ethyl vinyl ether to the corresponding Diels-Alder adducts 5 and 6 and with themselves to the cyclic dimerization products 7 and 8. The regiochemistry of the cycloadducts has been determined by chemical- and NMR-methods.The pyrolysis of 3-sulfolene 11 afforded the thiolactone 13 whose structure has been verified by X-ray diffraction analysis. In addition, the influence of Lewis acid catalysts on the Diels-Alder reaction and an approach to transition state calculation by means of the semiempirical AM 1 method has also been investigated.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19943360413
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  • 2
    Electronic Resource
    Electronic Resource
    Copper(I) complexes of mono- and bis-ferrocenyl-vinyl 2,2′-bipyridine-ligands: Synthesis and electrochemical properties (1996)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 338 (1996), S. 549-552 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New 2,2′-bipyridine ligands with one or two vinyl-ferrocenyl moieties (2, 3) have been synthezised. The coordination of the bipyridine by copper(I) ions allows the assembly of up to four ferrocenes in a defined arrangement. Although the ferrocene moieties are in close proximity, they are electronically independent, as is shown by UV-spectroscopy and cyclic voltammetry.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.199633801103
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  • 3
    Electronic Resource
    Electronic Resource
    Umlagerung von 3-Thioxo-Δ1,4-steroiden, ein neuer Zugang zu Steroidthiolen (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1397-1399 
    Details
    ISSN: 0947-3440
    Keywords: 3-Thioxoandrosta-1,4-dien-17-one, rearrangement of ; Thioestratriene ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Rearrangement of 3-Thioxo-Δ1,4-steroids, a New Approach of Steroid Thiols3-Thioxoandrosta-1,4-dien-17-one (1) is subjected to a dienthion-thiophenol rearrangement in aprotic and protic solvents in the presence of an acid catalyst resulting in the formation of 1-(acetylthio)-4-methylestra-1,3,5(10)-trien-17-one (2). 1-mercapto-4-methylestra-1,3,5(10)-trien-17-one (3), and the dimer 1,1′-(dithio)bis[4-methylestra-1,3,5(10)-trien-17-one] (4) as the reaction products. The mercapto compound 3 tends to be autoxidized to the sulfide 4.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199507189
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  • 4
    Electronic Resource
    Electronic Resource
    A new class of network-polymeric chiral stationary phases (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 7 (1995), S. 248-256 
    Details
    ISSN: 0899-0042
    Keywords: chiral discrimination ; chiral stationary phase ; network polymer ; DATD ; hydrogen bonding ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A strategy based on the use of homo bi- and multifunctional building blocks for the synthesis of a new class of network-polymeric chiral stationary phases has been evaluated. The key steps comprise acylation of N,N′-diallyl-L-tartardiamide (DATD) and reaction with a multifunctional hydrosilane, yielding a network polymer incorporating the bifunctional C2-symmetric chiral selector. Covalent bonding to a functionalized silica takes place during the latter process. Many of these chiral sorbents show interesting enantioselective properties toward a wide variety of racemic solutes under normal-phase (hexane-based) conditions. The retention is mainly caused by the hydrogen-bonding ability of the analyte, which is regulated by mobile phase additives like alcohol or ether cosolvents. The most interesting chiral stationary phases, in terms of broad enantioselectivity, were obtained from O,O′-diaryol-DATD-derivatives, particularly those containing the 3,5-dimethylbenzoyl and the 4-(tert-butyl)benzoyl moieties. Since high column efficiencies can be obtained with these chiral sorbents, an α-value of ca. 1.2 is usually sufficient to produce baseline separation. A large number of neutral as well as acidic or basic drug racemates are resolved without derivatization. © 1995 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530070411
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis and Spectroscopic Characterization of 4-Chlorophenyl Isocyanate (= 1-chloro-4-isocyanatobenzene) Adducts with Amino Acids as Potential Dosimeters for the Biomonitoring of Isocyanate Exposure (1998)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 81 (1998), S. 1254-1263 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Blood-protein adducts are used as dosimeter for modifications of macromolecules in the target organs where the disease develops. The functional groups of cysteine, tyrosine, serine, lysine, tryptophan, histidine and N-terminal amino acids are potential reaction sites for isocyanates. Especially the N-terminal amino acids, valine and aspartic acid of hemoglobin and albumin, respectively, are reactive towards electrophilic xenobiotics. To develop methods for the quantification of such blood-protein adducts, we treated 4-chlorophenyl isocyanate (1) with the tripeptide L-valyl-glycyl-glycine (2a) and with single amino acids yielding N-[(4-chlorophenyl)carbamoyl]valyl-glycyl-glycine (3a), N-[(4-chlorophenyl)carbamoyl]valine (3b), N-[(4-chlorophenyl)carbamoyl]aspartic acid (3c), N-(4-chlorophenyl)carbamoyl glutamic acid (3d), N-acetyl-S-[(4-chlorophenyl)carbamoyl]cysteine (3e), and N-acetyl-O-[(4-chlorophenyl)carbamoyl]serine (3f), Nα-acetyl-Nε-[(4-chlorophenyl)carbamoyl]lysine (3g). For several chemicals, it was shown that blood-protein adducts are good dosimeters of exposure and dosimeters for the target dose. The hydrolysis of the N-terminal adducts of isocyanates release hydantoins which can be separated from the rest of the protein and analyzed using GC/MS or HPLC. This was achieved with 3a. The released hydantoin could be analyzed using GC/MS. We propose to analyze the N-terminal adducts of isocyanates with blood protein to distinguish between arenamine and arylisocyanate exposure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19980810536
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  • 6
    Electronic Resource
    Electronic Resource
    Pyrazolo[3,4-d]pyrimidine 2′ -Deoxy- and 2′,3′ -Dideoxyribonucleosides: Studies on the glycosylation of 4-methoxypyrazolo[3,4-d]pyrimidine (1993)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 76 (1993), S. 1450-1458 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The glycosylation of the 4-methoxypyrazolo[3,4-d]pyrimidine (5) anion with 1-halo-2-deoxyribose 6 in MeCN/TDA-1 gives N2-deoxynucleoside 9 (29%) together with N1-isomer 7 (48%) and its anomer 8 (6%) [7]. The α-D-anomer 8 is not formed and the yield of the ß-D-anomer 7 increased to 62% when dimethoyethane is used as solvent and [18]crown-6 as catalyst. Employing 1-halo-2,3-dideoxyribose 10 instead of halogenose 6, the 2′,3′ -didexoynucleosides 12 and 14 were formed which desilylated (→ 1b and 2b) and converted into the ddI and ddA derivatives 3b (c7z8Idd), 15b (c7z8Add), and 17 (c7z8A′dd). Contrary to 7-deazapurine nucleotides, the triphosphates of 3b and 15b showed on appreciable activity against HIV-reverse transcriptase.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19930760405
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  • 7
    Electronic Resource
    Electronic Resource
    Benzofuran dioxetanes, a new class of mutagenic agents: Synthesis by photooxygenation of benzofuran derivatives (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 33-40 
    Details
    ISSN: 0170-2041
    Keywords: Benzofurans ; Singlet oxygen ; Photooxygenation ; Dioxetanes ; Mutagenicity ; Ames test ; Salmonella typhimurium ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Tetraphenylporphine-sensitized photooxygenation of benzofuran derivatives 1 afforded the corresponding benzofuran dioxetanes 2 in good yields. Allylic hydroperoxides 3 were formed regioselectively from 2,3-dimethyl-substituted benzofurans as minor products, except in the case of the benzofuran 1d, which gave predominantly the hydroperoxide 3d. The relative reactivities of the benzofurans toward singlet oxygen depended on the nature of substituents at the C-2 and C-3 positions of the furan rings. The benzofuran dioxetanes 2 were strongly mutagenic in the Salmonella typhimurium strain TA 100, their mutagenicity depending on the type of substituents of the dioxetane and of the benzo rings.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199119910106
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  • 8
    Electronic Resource
    Electronic Resource
    Synthesis and Application of a New Fluorescein Derivative for Fluorescent Labelling of Oligonucleotides and as a Novel Tool for Non-radioactive DNA Sequencing (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1051-1056 
    Details
    ISSN: 0170-2041
    Keywords: Xanthenes ; Fluorescein labelling ; Dyes ; Phosphoramidite synthesis ; Oligonucleotides ; DNA sequencing ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of 4(5)-(bromomethyl)fluorescein, which can be used as its 3′,6′-dibenzoyl derivative 7 for the labelling of nucleosides is described. Pyrimidine nucleosides such as 3′-and/or5′-protected 2′-deoxyuridine and thymidine are labelled by 7 at N3 of the heterocyclic base. The resulting base-labelled 3′-benzoyl-5′-dimethoxytrityl nucleosides may, on the one hand, be converted, after cleavage of the protective dimethoxytrityl group, into the 5′-phosphoramidite 11 by normal phosphorylation; on the other hand, 5′-triphosphates 13 are prepared by phosphorylation with 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one and pyrophosphate. The phosphoramidites 11 were sucessfully used for the fluorescent labelling of oligonucleotides during automatic DNA synthesis. The oligonucleotides can be used as primer in automatic non-radioactive DNA sequencing. The 5′-triphosphates 13 are potential substrates for DNA polymerases or terminal transferase.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301169
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  • 9
    Electronic Resource
    Electronic Resource
    Ringschlußreaktionen von syn-(E)- und anti-(E)-(2-Chinolylmethyl)- und -(1-Isochinolylmethyl)ketoximen zu Pyrazolo-[1,5-a]chinolinen und Pyrazolo[5,1-a]isochinolinenHerrn Prof. Dr. G. Manecke zum 65. Geburtstag gewidmet. (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1751-1759 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Ring Closures of syn-(E)- and (E)-(2-Quinolylmethyl)- and -(1-Isoquinolylmethyl)ketoximes to Pyrazolo[1,5-a]quinolines and Pyrazolo[5,1-a]isoquinolinesThe (2-quinolylmethyl)- and (1-isoquinolylmethyl)ketoximes 2a -e and 4a -d have been prepared and the oxime configurations determined. The Pyrazolo[1,5-a]quinolines 7a, b and the pyrazolo[5,1-a]isoquinoline 8a are formed by Beckmann reaction of the anti-isomers 2a, b and 4a, while O mesitylsulfonylhydroxylamine yields the pyrazolo compounds 7 and 8, independent of the oxime configuration.
    Notes: Die (2-Chinolylmethyl)- und (1-Isochinolylmethyl)ketoxime 2a-e und 4a-d wurden synthetisiert und die Oximkonfigurationen ermittelt. Durch Beckmann-Reaktion entstehen aus den anti-Isomeren 2a, b und 4a die Pyrazolo[1,5-a]chinoline 7a, b bzw. das Pyrazolo[5,1-a]isochinolin 8a, während mit O-Mesitylsulfonylhydroxylamin die Pyrazoloverbindungen 7 und 8 unabhängig von der Oximkonfiguration entstehen.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119811003
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  • 10
    Electronic Resource
    Electronic Resource
    P(III)-Acridinderivate als Synthesebausteine für die Festphasensynthese nichtradioaktiv markierter Oligonucleotide (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 1221-1225 
    Details
    ISSN: 0170-2041
    Keywords: Acridine labelling ; Phosphoramidites ; H-Phosphonates ; Oligonucleotide synthesis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: P(III)-Acridine Derivatives as Building Blocks for the Solid-Phase Synthesis of Non-Radioactively Labelled OligonucleotidesIn contrast to 9-(2-hydroxyethyl)-10-methylacridinium salts 5 9-(2-hydroxyethyl)acridine (2) proved to be a useful intermediate for the synthesis of 2-(9-acridinyl)ethyl phosphoramidites 8 or 2-(9-acridinyl)ethyl H-phosphonates 9 suitable for the introduction of acridine into oligonucleotides. The phosphorous compounds 8 and 9 were synthesized by modified standard procedures. The phosphoramidites and H-phosphonates of 2 are attached to the 5′ end of different oligonucleotides in the last cycle of the solid-phase synthesis.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001220
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