Reactions of Piroxicam with Alkyl Iodides.
1989
Alkylation of piroxicam with a homologous series of alkyl iodides gave reversibly formed O-alkyl products 1 as well as unexpected, irreversibly formed zwitterionic compounds 2, alkylated on the pyridine nitrogen, and O,N-bis-alkyl products 3. Proof of structure was accomplished by nmr and X-ray crystal analysis. Product distribution ratios were determined by hplc and are explained by the Hard-Soft Acid-Base principle.
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