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Preparation of pyrido[3,4‐ f ]‐1,4‐oxazepines O → N smiles rearrangement in 4‐substituted 3‐benzoylpyridines
Author(s) -
Radinov Rumen,
Haimova Marietta,
Simova Ekaterina,
Simova Svetlana
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880309
Subject(s) - chemistry , smiles rearrangement , reagent , selectivity , medicinal chemistry , potassium , stereochemistry , organic chemistry , catalysis
Preferential attack of mixed N,O‐dinucleophiles on 3‐benzoyl‐4‐chloropyridine ( 2 ) through the hydroxy function is achieved applying the potassium fluoride‐alumina reagent. This selectivity presents a route to pyrido[4,3‐ b ][1,5]benzoxazepines 5 and pyrido[3,4‐ f ]‐1,4‐oxazepines 12 . O→N Smiles rearrangement in the intermediate 4‐(2‐aminophenoxy)‐ and 4‐(2‐aminoethoxy)‐3‐benzoylpyridines 4 and 10 , respectively, is studied.