2,2′-(1,4-Phenylene)bis(7-nitro-1<i>H</i>-benzimidazole 3-oxide)

Abstract

Bis(benzimidazol-2-yl-3-oxide)benzene derivatives have potential applications as energetic or photoactive materials. By using a two-step one-pot approach employing microwave heating as a tool, 2,2′-(1,4-phenylene)bis(7-nitro-1H-benzimidazole 3-oxide) (1) has been prepared in 94% yield. In the first step an SNAr reaction is performed using p-xylylenediamine as the central building block. Without isolating the intermediate, a base-mediated cyclization reaction follows in the second step. The product was isolated in analytically pure form by means of a pH-controlled precipitation.

Keywords

• benzimidazole
• benzimidazole <i>N</i>-oxide
• microwave heating
• two-step one-pot
• precipitation