This paper describes our recent efforts to synthesize novel compound scaffolds integrating 2-quinoxalinolwith privileged structures of 1,3-dihydro-benzoimidazol-2-one, 1,3-dihydro-benzoimidazole-2-thione, 3-hydroxy-1
H-quinoxalin-2-one, 2
H-benzo[1,4]oxazin-3-ol, 2
H-benzo[1,4]thiazin-3-ol, and 1,3,4,5-tetrahydro-benzo[1,4]diazepin-2-one, respectively. Eight novel benzofused tricycles and their substituent diversity pointswere developed. These include pyrazino[2,3-
g]quinoxaline-2,8-diol (
I), 3-hydroxy-6,8,9,10-tetrahydro-1,4,6,10-tetraaza-cyclohepta[
b]naphthalen-7-one (
II), 6-hydroxy-4
H-1-oxa-4,5,8-triaza-anthracen-3-one (
III), 6-hydroxy-4
H-1-thia-4,5,8-triaza-anthracen-3-one (
IV), 6-hydroxy-1,1-dioxo-1,4-dihydro-2
H-1
6-thia-4,5,8-triaza-anthracen-3-one (
V), 6-hydroxy-1,3-dihydro-imidazo[4,5-
g]quinoxalin-2-one (
VI), 6-hydroxy-1,3-dihydro-imidazo[4,5-
g]quinoxaline-2-thione (
VII), and 7-hydroxy-1,4-dihydro-pyrazino[2,3-
g]quinoxaline-2,3-dione(
VIII). This strategy of integrating two benzofused privileged structures into one molecule may provide agreater chance for the discovery of novel lead compounds.