7 research outputs found
An anomalous behaviour of polychloroalicyclic ketones in gas chromatography and gas chromatography-mass spectrometry
No full textSynthesis of 7-Hydroxy(phenyl)ethylguanines by Alkylation of 2-Amino-6-chloropurine with Allyl-Protected Bromohydrins
No full textNew Modification of the Perkow Reaction: Halocarboxylate Anions as Leaving Groups in 3-Acyloxyquinoline-2,4(1H,3H)-dione Compounds
Get PDFSubstituovanĂ© 3-(fluoracyloxy)chinolin-2,4(1H,3H)-diony, mezi něž patřà 3-(fluorjodacetoxy)deriváty reagujĂ s triethyl-fosfitem za vzniku produktu Perkowovy reakce nebo odpovĂdajĂcĂho 4-ethoxychinolin-2(1H)-onu. V obou reakcĂch je jako odstupujĂcĂ skupina poprvĂ© pozorován fluorkarboxylátovĂ˝ anion. Toto pozorovánĂ omezuje vyuĹľitĂ intramolekulárnĂ Hornerovy-Wadsworthovy-Emmonsovy syntĂ©zy k modifikaci chinolin-2,4(1H,3H)-dionĹŻ uzavĹ™enĂm fluorovanĂ˝ch but-2-enolidovĂ˝ch kruhĹŻ.Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the first observed leaving group. This observation restricts the application of the intramolecular Horner-Wadsworth-Emmons synthesis to modify quinoline-2,4(1H,3H)-diones by the annulation of fluorinated but-2-enolide rings
