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Dibenz [b, f]‐1, 4‐oxazepin‐11 (10 H )‐one und Dibenz [b, e]‐1, 4‐oxazepin‐11 (5 H )‐one. 12. Mitteilung über siebengliedrige Heterocyclen
Author(s) -
Künzle F.,
Schmutz J.
Publication year - 1969
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19690520310
Subject(s) - chemistry , ring (chemistry) , medicinal chemistry , hydrolysis , stereochemistry , benzoic acid , closure (psychology) , product (mathematics) , organic chemistry , geometry , mathematics , economics , market economy
The syntheses of dibenzo [b, f]‐1, 4‐oxazepin‐11 (10 H )‐ones (I) with electron‐attracting substituents in position 2 by ring closure of the sodium salts of 2‐halogeno‐2′‐hydroxy‐benzanilides (II) are described. The reaction of II (R = SO 2 ·N(CH 3 ) 2 ) in N‐methylpyrrolidone also led, by S MILES rearrangement, to the isomeric minor product dibenzo [b, e]‐1, 4‐oxazepin‐11 (5 H )‐one (III; R = SO 2 ·N(CH 3 ) 2 ), whose constitution was proven by synthesis from VI. In the case of II (R = SO 2 ·CH 3 ), the 5‐methylsulfonyl‐2‐(2‐hydroxyanilino)‐benzoic acid (VI; R = SO 2 ·CH 3 ) was obtained directly after hydrolysis. The lactam I (R = NO 2 ) was rearranged to the corresponding acid VI by heating with dilute caustic soda.