Scheme 1.
The synthetic pathway to generate naphthoquinone derivatives 9–16. Compounds 9–16 are synthesized from the corresponding aromatic amines and 2,3-dichloronaphthoquinone [1,4,19,20,21]. By using aryl urea in this reaction instead of an aromatic amine, we hoped to form an oxazole ring, but we failed to form 2-chloro-3-(phenylamino)-1,4-naphthoquinones 9–15 or 2-(4-hydroxyphenylamino)-1,4-naphthoquinone 16.