SYNTHESIS OF 1,4-NAPHTHOQUINONE DERIVATIVES VIA REACTION WITH ARYLAMIDOXIMES
1,4-naphthoquinone, arylamidoxime, oxadiazine
The aim of this work was to synthesize 1,4-naphthoquinones containing an imidazole heterocyclic nucleus. Initially, 2,3-dibromo-1,4-naphthoquinone (49b), 2-bromo-1,4-naphthoquinone (49a) and different arylamidoximes (9a-g) were synthesized. In the first stage, the reaction between compound 49b and arylamidoximes 9a-g took place, resulting in seven new compounds containing the oxadiazine core 51a-g, obtaining yields of 59-84%. Using compound 49a in the reaction with arylamidoximes 9a-g, another seven novel compounds were obtained, 53a-g, showing yields of 62-94%. In the second part, the oxygen of the arylamidoximes was protected with benzoyl chloride, leaving only the amino group available, in an attempt to reach intermediate 56a and, subsequently, the imidazole ring. However, it was not possible to reach intermediate 56a due to the cyclization of compound 57a.