8-chloro-5-methyl-11-(2-(m-tolyl)hydrazineyl)-5H-indolo[2,3-b]quinoline (**B7**)

Yield, 80%; gray solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 8.78 (s, 1H), 8.55 (d, *J* = 8.8 Hz, 1H), 8.18 (d, *J* = 8.8 Hz, 1H), 8.09–8.02 (m, 1H), 7.70 (t, *J* = 7.8 Hz, 1H), 7.57 (s, 1H), 7.22 (d, *J* = 9.0 Hz, 1H), 7.13 (t, *J* = 7.8 Hz, 1H), 6.76 (d, *J* = 2.3 Hz, 1H), 6.72 (d, *J* = 7.5 Hz, 2H), 4.23 (s, 3H), 2.23 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 152.79, 148.12, 139.19, 138.44, 136.94, 133.49, 130.94, 129.46, 124.61, 122.38, 121.90, 120.24, 116.85, 114.06, 113.85, 111.40, 110.85, 97.50, 56.51, 35.17, 18.18. MS-ESI *m*/*z*: calcd for C23H19ClN4[M+H] +: 387.1291; found: 387.2803.

#### 8-chloro-5-methyl-11-(2-(p-tolyl)hydrazineyl)-5H-indolo[2,3-b]quinoline (**B8**)

Yield, 71%; light yellow solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 8.76 (s, 1H), 8.57 (d, *J* = 8.8 Hz, 1H), 8.17 (d, *J* = 8.7 Hz, 1H), 8.05 (d, *J* = 8.5 Hz, 1H), 7.70 (m, 1H), 7.57 (s, 1H), 7.21 (d, *J* = 8.9 Hz, 1H), 7.06 (d, *J* = 8.1 Hz, 2H), 6.88–6.78 (m, 2H), 4.23 (s, 3H), 2.21 (s, 3H). 13C NMR (100 MHz, DMSO) *δ* 152.81, 148.40, 145.69, 138.41, 136.92, 134.11, 130.93, 130.85, 129.94(2C), 128.38, 124.58, 122.35, 120.18, 116.79, 113.71(2C), 111.35, 100.65, 98.74, 97.10, 33.57, 19.93. MS-ESI *m*/*z*: calcd for C23H19ClN4[M + H]+: 387.1285; found: 387.2360.
