Propionic acids in organic synthesis: Novel synthesis of benzimidazole, 3,1-benzoxazine, 3-aminoquinazoline and 3-aminothieno[2,3-<i>d</i>]pyrimidine derivatives containing 2-naphthyl propionyl moiety

Abstract

Naproxenoyl chloride <b style="">2</b> is reacted with some nucleophilic reagents as ammonium thiocyanate and sodium azide to produce the novel isothiocyanate <b style="">3</b> and azide <b style="">4</b> derivatives, respectively. Interaction of isothiocyanate <b style="">3</b> with 1,2-phenylenediamine and anthranilic acid has produced the corresponding benzimidazole <b style="">5</b> and 3,1-benzoxazine <b style="">7</b> derivatives, respectively. Treatment of acid azide <b style="">4</b> with <i>p</i>-toluidine afforded urea derivative <b style="">9</b>. The novel quinazolinone <b style="">11</b> was synthesized by acylation of methyl anthranilate with acid chloride <b style="">2</b> followed by treatment with hydrazine hydrate.