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Reaction of N ‐(2‐pyridylmethyl)‐3,5‐dimethylbenzamide and N ‐(3‐pyridylmethyl)‐3,5‐dimethylbenzamide N ‐oxides with acetic anhydride
Author(s) -
Braña Miguel F.,
Rodriguez María Luz López
Publication year - 1982
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.5570190607
Subject(s) - acetic anhydride , chemistry , pyridine , medicinal chemistry , oxide , acetic acid , pyridine n oxide , pummerer rearrangement , organic chemistry , catalysis
As a continuation of our work on the reaction of N ‐pyridylmethyl‐3,5‐dimethylbenzamide N ‐oxides with acetic anhydride, we now report a study of the reaction of N ‐(2‐pyridylmethyl)‐3,5‐dimethylbenzam.de N ‐oxide ( 5 ) and N ‐(3‐pyridylmethyl)‐3,5‐dimethylbenzamide N ‐oxide ( 6 ) with acetic anhydride. Compound 5 gave N,N ′‐di(3,5.dimethylbenzoyl)‐1,2‐di(2.pyridyl)ethenediamine ( 7 ) and 3,5‐dimethylbenzamtde ( 8 ). Compound 6 afforded three products formulated as 2‐acetoxy‐3‐(3,5‐dimethylbenzoylaminomethyl)pyridine ( 12 ), 3‐(3,5‐dimethylbenzoylaminomethyl)‐2‐pyridone ( 13 ) and 5‐(3,5‐dimethylbenzoylaminomethyl)‐2‐pyridone ( 14 ). Analytical and spectral data are presented which support the structures proposed.