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  • 1
    Electronic Resource
    Electronic Resource
    Fünfringheterocyclen, VI. 3-Organylamino-1,3-thiazolin-2-one und -2-thione (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 656-674 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Five-Membered Heterocycles, VI. - 3-Organylamino-1,3-thiazolin-2-ones and -2-thionesS-Potassium (N'-organylhydrazino)monothio- and potassium (N-organylhydrazino)dithioformates 1A and 1B are alkylated at the mercapto sulfur atom with α-halo ketones to form the acylmethyl (hydrazino)thioformates 2 A and 2B, which can be obtained pure, or their cyclic derivatives 2'A and 2'B, respectively. In acidic solution these products are transformed into 3-organylamino-1,3-thiazolin-2-ones 3A or -2-thiones 3B, respectively. Proof for the five-membered ring structure comes from chemical reactions and UV spectroscopy. The syn-anti-diastereomeric S,S'-dialkyl dithiocarbonate tosylhydrazones Z-5 and E-5 have been prepared and their stereochemistry assigned.
    Notes: S-Kalium-[(N-organylhydrazino)monothio- und Kalium-[(N-organylhydrazino)dithioformiate] 1A bzw. 1B lassen sich mit α-Halogenketonen am Mercapto-Schwefel zu rein isolierbaren (Hydrazino)thioameisensäure-acylmethylestern 2Abzw. 2B oder deren cyclischen Derivaten 2'A bzw. 2'B alkylieren. Diese ergeben in saurer Lösung 3-Organylamino-1,3-thiazolin-2-one 3A bzw. -2-thione 3B. Der Beweis für das Vorliegen der fünfgliedrigen Ringstruktur wurde durch chemische Reaktionen und UV-spektroskopisch erbracht. Die syn-anti-diastereomeren Dithio-kohlensäure-S,S'-dialkylester-tosylhydrazone Z-5 und E-5 wurden hergestellt und zugeordnet.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790510
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  • 2
    Electronic Resource
    Electronic Resource
    Fünfringheterocyclen, IV. Ringverengung von 5-Aryl-6H-1,3,4-thiadiazin-2(3H)-onen zu 4-Aryl-1,2,3,-thiadiazolen (1977)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 791-799 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Five-Membered Heterocycles, IV.  -  Ring Contraction of 5-Aryl-6H-1,3,4-thiadiazin-2(3H)- ones to 4-Aryl-1,2,3-thiadiazoles5-Aryl-6H-1,3,4-thiadiazin-2(3H)-ones 3α have been prepared via two different routes (A and B). Oxidation with chlorine-containing tert-butyl hypochlorite led via ring contraction and extrusion of carbon dioxide to the 4-aryl-1,2,3-thiadiazoles 9.
    Notes: 5-Aryl-6H-1,3,4-thiadiazin-2(3H)-one 3α wurden auf zwei verschiedenen Wegen (A und B) dargestellt. Die Oxidation mit chlorhaltigem tert-Butylhypochlorit führte unter Ringverengung und Abspaltung von Kohlendioxid zu den 4-Aryl-1,2,3-thiadiazolen 9.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197719770509
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