Reaction of  N ‐(2‐pyridylmethyl)‐3,5‐dimethylbenzamide and  N ‐(3‐pyridylmethyl)‐3,5‐dimethylbenzamide  N ‐oxides with acetic anhydride | Zendy

Braña Miguel F. | Zendy; Rodriguez María Luz López | Zendy

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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.

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