Abstract:
<jats:p>3-Substituted salicyloyl chlorides were converted to salicyloyl azides (R = Br, NO<jats:sub>2</jats:sub>) which underwent thermal rearrangement and intramolecular cyclization to benzoxazolinones. The crystal structures of 7-substituted benz[d]oxazolin-2-ones (R = Br, NH<jats:sub>2</jats:sub>), intermediate salicyloyl azides and byproducts, i. e. 3-(2-hydroxy-3-nitrophenyl)-8-nitrobenz[e][1,3]oxazine-2,4-dione and 2-hydroxy-N- (2-hydroxy-3-nitrophenyl)-3-nitrobenzamide, have been determined. 7-Aminobenzoxazolinone was obtained by catalytic hydrogenation of the nitro compound as the hemihydrate or in anhydrous form, depending on the temperature of the crystallization</jats:p>
Description:
<jats:p>3-Substituted salicyloyl chlorides were converted to salicyloyl azides (R = Br, NO<jats:sub>2</jats:sub>) which underwent thermal rearrangement and intramolecular cyclization to benzoxazolinones. The crystal structures of 7-substituted benz[d]oxazolin-2-ones (R = Br, NH<jats:sub>2</jats:sub>), intermediate salicyloyl azides and byproducts, i. e. 3-(2-hydroxy-3-nitrophenyl)-8-nitrobenz[e][1,3]oxazine-2,4-dione and 2-hydroxy-N- (2-hydroxy-3-nitrophenyl)-3-nitrobenzamide, have been determined. 7-Aminobenzoxazolinone was obtained by catalytic hydrogenation of the nitro compound as the hemihydrate or in anhydrous form, depending on the temperature of the crystallization</jats:p>