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Eine breit anwendbare Synthese fluoreszierender kondensierter α-Pyrone
Authors:Wolfbeis  Otto S  Ziegler  Erich  Knierzinger  Andreas  Wipfler  Helmut  Trummer  Iris
Institution:(1) Institut für Organische Chemie, Universität Graz, A-8010 Graz, Österreich
Abstract:In a two step procedure and in usually good yield an agr-pyrone ring can be annelated to (enolized) cyclic beta-dicarbonyl compounds like 4-hydroxy-2-pyrones, 4-hydroxycoumarins, 4-hydroxy-2-quinolones and more complex malonylheterocycles, but also to beta-naphthole.In a first step the combined action of triethyl orthoformate and arylamines upon the dicarbonyl system affords the anilinomethylene derivativesB in usually high yields.B is reacted with an active methylene nitrile (like alkyl cyano-acetates) and one equivalent of a strong base (like sodium methoxide or potassium hydroxide) in a polar aprotic solvent (like dimethylformamide). Subsequent acidification with dilute aqueous acid gives the corresponding agr-pyroneD with yields from 18 to 84%.The reaction sequence is broadly applicable, which is demonstrated by the synthesis of a series of known (3, 7, 16, 31) and novel (10, 19, 22, 25, 28, 34) heterocyclic systems. Most of them exhibit strong fluorescence in the visible with emission maxima between 450 and 510 nm.
208. Mitt.:H. Wittmann undF. Günzl, Z. Naturforsch.33b, 1540 (1978).
Keywords:Enamines  Fluorescence  agr-Pyrone" target="_blank">gif" alt="agr" align="BASELINE" BORDER="0">-Pyrone  synthesis
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