Synthesis of 2-Aminobenzoxazoles from 2-Aminophenols

Significance

Reported is the synthesis of 2-aminobenzoxazoles from the corresponding 2-aminophenols using orthocarbonate lynchpin reagents. Broad scope for the reaction was established, with cyclic secondary amines giving the highest yields, while volatile or hindered amines performed poorly. Substitution of the amino­phenol component is well tolerated. The use of 1,1-dichlorodiphenoxymethane in place of the ­orthocarbonate proved efficacious when side reactions such as amide formation were observed.