✦ LIBER ✦

Heterocyclensynthesen mit 5-Phenyl-isoxazoliumsalzen; Synthese von 1H-2-Benzoylmethylen-2,3,6,7-tetrahydro-3,6,7,7-tetramethyl -pyrrolo[3,4-d]pyrimidin-4,5-dion

✍ Scribed by Hans-Georg Henning; Kerstin Rothe

Publisher: Wiley (John Wiley & Sons)
Year: 2010
Weight: 280 KB
Volume: 28
Category: Article
ISSN: 0044-2402
DOI: 10.1002/zfch.19880280913

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✦ Synopsis

Alkylierungsmittel vom Typ der a-Brom-a-ethoxyessigsaurederivate [l] erwiesen sich in vorangegangenen Untersuchungen als geeignete Synthone zur reversiblen Blockierung von Carboxylgruppen iiber enzymatisch spaltbare Alkoxycarbonyl-ethoxymethylester [a] sowie zur Herstellung entsprechender bioabbaubarer Polyester [3]. In Fortfuhrung dieser Arbeiten interessierten uns weitere 0und C-Alkylierungsreaktionen der leicht zugiinglichen Amide und Ester 1 [l]. Wir fanden, dad a-Brom-a-ethoxy-acetamide mit Triethylammoniumsalzen von Carbonsawen in Dichlormethan bei 2O-4O0C in guten Ausbeuten die entsprechenden Alkylaminocarbonylethoxymethylester bilden. So entsteht aus dem Piperidid 1 (X = C,H,,N) und Propionat in 7l%iger Ausbeute der Ester 2. Bei der Einwirkung von Esterasen, 2.B. einer wiiBrigen Losung von lyophilisiertem Normalserum vom Pferd, wird 2 bei 35°C in 2 h

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