Synthese und Reaktionen von 3‐Acyl‐2‐methylthio‐chromonen¹)

Abstract

Die 3-Acyl-2-methylthio-chromone 5a, Sc und 5d reagieren mit Hydroxid-und Alkoxidionen sowie Aminen unter Verdrangung der Methylthio-Gruppe zu den in 2-Stellung substituierten 3-Acyl-chromonen 8 und 1Oa-lop bnv. den 3-Acyl-4-hydroxy-cumarinen 6a und 6b. Mit Hydrazin, Hydroxylamin, o-Phenylendiamin, Guanidin und Amidin-Derivaten entstehen die anellierten Chromone lla-llc, U , 1 3 und 14a-14e. Synthesis and Reactions of 3-Acyl-2-(methylthio)chromones3-Acyl-2-(methylthio)chromones 5a, 5c and 5d react with hydroxide or alkoxide ions or with amines to yield the substituted 3-acylchromones 8,10a-lOp, or the 3-acyl-4-hydroxycoumarins 6a and 6b. With hydrazine, hydroxylamine, o-phenylenediamine, guanidine or amidine derivatives the fused chromones lla-llc, U , 1 3 and 14-14e are obtained.Wir haben vor einiger Zeit gefunden, daB beim Umsetzen des Bis-(hydroxybenzoy1)methans 1 mit Schwefelkohlenstoff, Kaliumhydroxid und Dimethylsulfat das Chromonochromon 3 entsteht*). Dabei ergab sich, daR 3-Acyl-2-methylthio-chromone von der Art des hier formulierten Zwischenprodukts 2 dann in guten Ausbeuten isolierbar sind, wenn die Benzoylgruppe unsubstituiert ist Da 3-Acylchromone antiallergisch wirken sollen4) und man bei 2-Aminochromon-Derivaten zentrale, insbesondere antikonvulsive Eigenschaften gefunden hat5), haben wir die 3-Acyl-2-methylthio-chromone 5a,5c und 5d nach dem angegebenen Verfahren'') aus den 1,3-Dicarbonylverbindungen 4a, 4c und 4d hergestellt und untersucht, ob sie sich zur Synthese von 3-Acyl-2-amino-chromonen eignen.oder an Stelle der Hydroxyl-eine Methoxylgruppe sitzt (5b)".

Centro‐symmetric copper complex as a novel antitumor drug for therapeutic applications: Fabrication, structure, theoretical calculations, cytotoxicity, DNA binding/cleavage, and molecular docking

“…Upon coordination, the stretching vibrations of (C=O) acetyl and (C‐O) phenolic groups have been shifted to low frequency, signifying the coordination of these groups with copper ions. [ 47 ] The involvement of previously shifted groups has been further supported by the appearance of nonligand bands at 575 and 597 cm −1 , which is associated with ν(M‐O). [ 48–50 ] Finally, the AHC is coordinated to the metal ion in a monoanionic form with bidentate through O, O donor atoms, as can be seen from the description previously.…”

New Potent SARS‐CoV 3C‐Like Protease Inhibitors Derived from Thieno[2,3‐d]‐pyrimidine Derivatives

“…The reaction of compound 1 with indole‐3‐carbaldehyde ( 2a ) and with 4,9‐dimethoxy‐5‐oxo‐5 H ‐furo[3,2‐g]chromene‐6‐carbaldehyde ( 2b ) was conducted in DMF in the presence of hydrochloric acid. Apparently, under these conditions the initially formed azomethines (cf.…”

3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and applications

“…The structure of 3-acetyl-4-hydroxycoumarin has been assigned by UV (Klutchko et al, 1974;Traven et al, 1997), IR (Naceur et al, 2011;Eiden and Rademacher, 1983;Babin et al, 1981), MS (Naceur et al, 2010;Fischmeister et al, 2011;Sukdolak et al, 2004), NMR (Li et al, 2012a;Athanasellis et al, 2004;Kravchenko et al, 1999), fluorescence (Li et al, 2012a) and photoelectron (Traven et al, 2000) spectroscopy. The UV-Vis absorption and photoluminescence spectra of 3-acetyl-4-hydroxycoumarin in dilute dichloromethane solutions revealed a sharp absorption peak at 300 nm, with a shoulder at 341 nm (Li et al, 2012a).…”