Synthesis of 6,7-dihydroxy-3-aryl-5-undecyl-4,1,2-benzoxadiazines

Abstract

<smarttagtype namespaceuri="urn:schemas-microsoft-com:office:smarttags" name="metricconverter"> Condensation of Embelin <b>1</b> with different aromatic acid hydra­zides <b>2</b> in glacial acetic acid to give N¹-5-hydroxy-6-unde­cyl-<i>p</i>-benzoaquinone-2-yl)-benzohydrides <b>3</b>. Reductive cycli­za­tion of the product <b>3</b> with simultaneous acetylation <i>in situ</i> resulted in the formation of the compound <b>4</b> 1-N-acetyl-6,7-diacetyl-3-aryl-5-undecyl-4,1,2-benzoxadiazine. In the final step the compound <b>4</b> is deacetylated to give the title products <b>5</b>. The structures of the newly prepared compounds have been confirmed from analytical and spectral data. Some of the compounds exhibited antibacterial and antifungal activity. </smarttagtype>