Friedel-Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S2O82−) in the presence of the visible light catalyst, Ru(bpy)3Cl2, at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron–rich arenes served as effective nucleophiles, forming new C–O or C–C bonds. In general, photocatalysis provided higher yields and better selectivities.
The 6-desfluoroquinolones (6-DFQs) are anti-HIV agents that target Tat-mediated transcription. This particular mechanism of action makes this class of compounds very attractive for further structural investigations. Identification of the pharmacophore required for inhibition will ultimately result in the design of more selective analogues for use in combination therapy for the treatment of HIV infections. We have focused on the pyridone ring of the quinolone nucleus present in these compounds, designing new modifications to broaden the structure-activity relationship knowledge base. Herein, we present novel and very potent anti-HIV quinolones, most notably those bearing an amino or vinyl group at the N1 position. Attempts were made to determine the structural parameters necessary to impart potent anti-HIV activity to the vinyl derivatives.
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