• Media type: E-Article
  • Title: Synthesis of Substituted Benzoxazolinones by the Curtius Rearrangement: Crystal Structures of Intermediates and By-Products
  • Contributor: Laus, Gerhard; Kahlenberg, Volker; Wurst, Klaus; Nerdinger, Sven; Schottenberger, Herwig
  • Published: Walter de Gruyter GmbH, 2011
  • Published in: Zeitschrift für Naturforschung B
  • Extent: 479-486
  • Language: English
  • DOI: 10.1515/znb-2011-0507
  • ISSN: 1865-7117; 0932-0776
  • Keywords: General Chemistry
  • 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>
  • Footnote:
  • Access State: Open Access