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- W1984674986 abstract "Bei der Umsetzung von 2-Thiocytosin (3) mit Jodacetamid in Wasser wird die Carbonsaure 5, in alkoholischer Losung der Ester 6 bzw. 7 gebildet. Die Darstellung des Amids 4 gelingt nur in alkalischer Losung. Nach Alkylierung von 3 mit 3-Jodpropionamid (12) anstelle von Jodacetamid verlangsamt sich die Hydrolyse deutlich. Die Amidhydrolyse wird vollstanding unterdruckt, wenn 2-Thiocytosin an N-1 alkyliert ist. Die kinetische Analyse der pH-abhangigen Amidhydrolyse fuhrt zu einem Mechanismus-Vorschlag fur die intramolekulare Katalyse unter Beteiligung des Pyrimidinsystems.Intramolecular Catalysis of Hydrolysis of (Pyrimidinylthio)carboxamides by PyrimidineRing-SystemsOn treatment of 2-thiocytosine (3) with iodoacetamide, in water the formation of the carboxylic acid 5 and in alcoholic solution the formation of ester 6 or 7 respectively was observed. The amide 4 could only be prepared in alkaline medium. After alkylation of 3 with 3-iodopropionamide (12) instead of iodoacetamide a marked reduction in the rate of hydrolysis is observed. The amide hydrolysis is completely prevented, if the N-1-nitrogen of 3 is alkylated. Kinetic analysis of the pH-dependent amide hydrolysis suggests a mechanism for intramolecular catalysis by pyrimidine ring-systems." @default.
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- W1984674986 date "1976-11-01" @default.
- W1984674986 modified "2023-09-26" @default.
- W1984674986 title "Intramolekulare Katalyse des Pyrimidin-Systems bei der Hydrolyse von (Primidinylthio)carbonsäureamiden" @default.
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- W1984674986 doi "https://doi.org/10.1002/cber.19761091115" @default.
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