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  • 1
    Electronic Resource
    Electronic Resource
    Zur Synthese von (Z)- und (E)-3-(1H-Imidazol-4-yl)-2-propenamin und einigen 3-(1H-Imidazol-4-yl)propanaminen (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 317-323 
    Details
    ISSN: 0170-2041
    Keywords: Homohistamine ; Imidazole derivatives ; 2-Propenamine derivatives ; Impromidine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of (Z)- and (E)-3-(1H-imidazol-4-yl)-2-propenamine and Some 3-(1H-imidazol-4-yl)propanamines3-(1H-Imidazol-4-yl)propanamine (6, homohistamine), an essential intermediate for the synthesis of potent impromidine-type histamine H2 receptor agonists, is efficiently prepared from trans-urocanic acid (1) by reduction of the methyl ester 2 and conversion to the saturated amide 4. Dehydration with thionyl chloride yields the nitrile 5 which is subsequently reduced to 6. Side-chain methylated 3-(1H-imidazol-4-yl)propanamines 12 are available from 1H-imidazole-4-carbaldehyde (7) and 1-(1H-imidazol-4-yl)ethanone (8), respectively, via unsaturated nitriles 10 and stepwise reduction. Cyclization of the appropriate 4-bromo-5-oxohexanenitriles 14α with formamidine in liquid ammonia and reduction of the obtained nitriles 15 furnishes ring-methylated amines 16. (E)-3-(1H-Imidazol-4-yl)-2-propenamine [(E)-23] is obtained in six steps from the trans-ester 2 while (Z)-23 is accessible by treating 7 with triphenyl(2-phthalimidoethyl)phosphonium bromide (17) and final deprotection. These primary amines are valuable intermediates for the synthesis of impromidine analogues.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199219920158
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  • 2
    Electronic Resource
    Electronic Resource
    Racemattrennung, Kristallstruktur und histaminartige Wirkung von 4-[1-(2-Aminoethylthio)ethyl]-5-methylimidazol (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 678-683 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Resolution, Crystal Structure, and Histamine-like Activity of 4-[1-(2-Aminoethylthio)ethyl]-5-methylimidazoleThe resolution of racemic 4-[1-(2-aminoethylthio)ethyl]-5-methylimidazole (1) using optically active Di-O-(P-toluoyl)tartaric acid as well as the histamine-like activity of the enantiomers are described. The crystal structure of (+)-1 · 2HCl · H2O has been determined and refined until R = 0.0483. Accordingly, (+)-1 is R configurated. Only (S)-(-)-1 possesses H1-agonistic activity.
    Notes: Es wird die Racemattrennung von 4-[1-(2-Aminoethylthio)ethyl]-5-methylimidazol (1) mittels optisch aktiver Di-O-(p-toluoyl)weinsäure sowie die histaminartige Wirksamkeit der Enantiomeren beschrieben. Von (+)-1 · 2HCl · H2O wurde die Kristallstruktur bestimmt und bis zu einem R-Wert von 0.0483 verfeinert. Danach ist (+)-1 R-konfiguriert. Von den beiden Enantiomeren besitzt nur (S)-(-)-1 H1-agonistische Aktivität.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830416
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