© 2019 Chemical Society of Pakistan. All rights reserved.Summary: In this study, new 1,4-naphtho- and 5-nitro-1,4-naphtho derivatives containing N- and N,N-substituted groups which has not been reported yet, have been synthesized from 2,3-dichloronaphthalene-1,4-diones (1,9). Compounds of 2-choloro-3-((2,4,6-triflorophenyl)amino)naphthalene-1,4-dione (3) and 2-chloro-3-((4-florophenyl)amino)naphtalene-1,4-dione (7) were obtained by reactions of 2,3-dichloronaphthalene-1,4-dione 1 with 4-fluoroaniline (6) and 2,4,6-trifloroaniline (2), respectively involving a Michael addition. We reported the cyclization reactions of compounds 1 to benzo[g]pirido[3,2-b]quinoxaline-6,11(5H,12H)-dione (5) synthesized. The N-substituted naphthoquinone 7 was reacted with sodium azide in dimethylformamide and 2-florobenzo[b]phenazin-6,11-dione (8) was obtained as the one cyclized compound. Regioisomers 3-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-2-chloro-5-nitronaphthalene-1,4-dione 11 and 2-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-chloro-5-nitronaphthalene-1,4-dione 12 were obtained from reaction of 2,3-dichloro-5-nitronaphthalene-1,4-dione 9 with 1-piperonylpiperazine (10).