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Reactions of piroxicam with alkyl iodides
Author(s) -
Hammen Philip D.,
Berke Helen,
Bordner Jon,
Braisted Andrew C.,
Lombardino Joseph G.,
Whipple Earl B.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260103
Subject(s) - chemistry , alkyl , alkylation , piroxicam , pyridine , homologous series , base (topology) , medicinal chemistry , organic chemistry , catalysis , pathology , medicine , mathematical analysis , alternative medicine , mathematics
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.