ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 = SO2·N(CH3)2) in N-methylpyrrolidone also led, by SMILES rearrangement, to the isomeric minor product dibenzo [b, e]-1, 4-oxazepin-11 (5 H)-one (III; R = SO2·N(CH3)2), whose constitution was proven by synthesis from VI. In the case of II (R = SO2·CH3), the 5-methylsulfonyl-2-(2-hydroxyanilino)-benzoic acid (VI; R = SO2·CH3) was obtained directly after hydrolysis. The lactam I (R = NO2) was rearranged to the corresponding acid VI by heating with dilute caustic soda.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19690520310
