Synthesis and antibacterial studies of azodispersed dyes
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128.9, 127.1, 126.9, 126.7, 126.4, 125.1, 124.1, 103.6,
45.5, 42.3, 19.8 ppm.
filtered off, thoroughly dried, and recrystallized from a
suitable solvent to give 4a–4n.
2-[4-Methyl-5-(phenylazo)thiazol-2-yl]-2,3,4a,5,10,10a-
hexahydro-5,10-benzenobenzo[g]phthalazine-1,4-dione
(4a, C28H21N5O2S)
2-[5-(4-Bromophenylazo)-4-methylthiazol-2-yl]-
2,3,4a,5,10,10a-hexahydro-5,10-benzenobenzo[g]-
phthalazine-1,4-dione (4e, C28H20BrN5O2S)
Crystallization from EtOH-benzene afforded 1.97 g (80%)
4a, reddish brown. M.p.: 248 °C; IR (KBr): v = 3,220
Crystallization from DMF-MeOH afforded 2.054 g (72%)
4e, reddish brown. M.p.: 295 °C; IR (KBr): v = 3,208
1
(NH), 1,770, 1,696 (CO), 1,506 (N=N) cm-1; H NMR
1
(NH), 1,760, 1,698 (CO), 1,520 (N=N) cm-1; H NMR
(200 MHz, DMSO-d6): d = 2.4 (s, 3H, CH3), 3.4 (s, 2H,
C11-H, C12-H), 4.9 (s, 2H, C9-H, C10-H), 7.0–7.7 (m,
13H, Ar–H), 12.0 (s, 1H, NH) ppm; 13C NMR (100 MHz,
DMSO-d6): d = 172.1, 169.4, 142.6, 139.6, 129.3, 128.8,
127.6, 126.8, 125.5, 124.7, 108.3, 45.0, 40.8, 20.5 ppm.
(400 MHz, DMSO-d6): d = 2.5 (s, 3H, CH3), 3.2 (s, 2H,
C11-H, C12-H), 4.8 (s, 2H, C9-H, C10-H), 7.2–7.6 (m,
12H, Ar H), 10.9 (br, 1H, NH) ppm; 13C NMR (100 MHz,
DMSO-d6): d = 171.9, 171.1, 168.9, 142.5, 139.6, 132.8,
128.5, 126.8, 125.5, 124.7, 106.4, 45.0, 40.8, 20.1 ppm.
2-[4-Methyl-5-(4-methylphenylazo)thiazol-2-yl]-
2,3,4a,5,10,10a-hexahydro-5,10-benzenobenzo[g]-
phthalazine-1,4-dione (4b, C29H23N5O2S)
2-[4-Methyl-5-(4-nitrophenylazo)thiazol-2-yl]-
2,3,4a,5,10,10a-hexahydro-5,10-benzenobenzo[g]-
phthalazine-1,4-dione (4f, C28H20N6O4S)
Crystallization from EtOH-benzene afforded 2.33 g (92%)
4b, orange. M.p.: 304 °C; IR (KBr): v = 3,128 (NH),
Crystallization from DMF-MeOH afforded 2.039 g (76%)
4f, brown. M.p.: 263 °C; IR (KBr): v = 3,216 (NH), 1,702
1,714 (CO), 1,512 (N=N) cm-1 1H NMR (200 MHz,
;
(CO), 1,514 (N=N), 1332 (NO2) cm-1
;
1H NMR
DMSO-d6): d = 2.35 (s, 3H, CH3–C6H4), 2.45 (s, 3H,
CH3), 3.3 (s, 2H, C11-H, C12-H), 4.8 (s, 2H, C9-H, C10-
H), 7.1–7.6 (m, 12H, Ar–H), 11.9 (s, 1H, NH) ppm; 13C
NMR (100 MHz, DMSO-d6): d = 173.6, 171.4, 169.0,
145.3, 140.0, 138.5, 138.4, 129.5, 127.0, 126.8, 126.0,
125.1, 124.2, 104.4, 45.2, 43.5, 21.4, 20.1 ppm.
(200 MHz, DMSO-d6): d = 2.25 (s, 3H, CH3), 3.35 (s,
2H, C11-H, C12-H), 4.85 (s, 2H, C9-H, C10-H), 7.1–7.9
(m, 12H, Ar–H), 12.3 (s, 1H, NH) ppm; 13C NMR
(100 MHz, DMSO-d6): d = 176.4, 174.8, 169.0, 149.6,
147.2, 141.0, 139.4, 135.2, 129.8, 126.9, 126.8, 125.7,
124.3, 103.6, 46.6, 45.4, 18.9 ppm.
2-[5-(4-Methoxyphenylazo)-4-methylthiazol-2-yl]-
2,3,4a,5,10,10a-hexahydro-5,10-benzenobenzo[g]-
phthalazine-1,4-dione (4c, C29H23N5O3S)
Ethyl 4-[2-(3,4,4a,5,10,10a-hexahydro-1,4-dioxo-5,10-
benzenobenzo[g]phthalazin-2(1H)-yl)-4-methylthiazol-5-
ylazo]benzoate (4g, C31H25N5O4S)
Crystallization from DMF-H2O afforded 2.217 g (85%) 4c,
reddish brown. M.p.: 245 °C; IR (KBr): v = 3,225 (NH),
Crystallization from EtOH afforded 1.945 g (69%) 4g, red.
M.p.: 241 °C; IR (KBr): v = 3,240 (NH), 1,706 (br, CO),
1,706 (CO), 1,509 (N=N) cm-1 1H NMR (200 MHz,
;
1,514 (N=N) cm-1 1H NMR (400 MHz, DMSO-d6):
;
CDCl3): d = 2.4 (s, 3H, CH3), 3.3 (s, 2H, C11-H, C12-H),
3.85 (s, 3H, OCH3), 4.85 (s, 2H, C9-H, C10-H), 6.9 (d, 2H,
Ar–H), 7.1–7.4 (m, 8H, Ar–H), 7.7 (d, 2H, Ar–H), 10.3 (s,
1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 172.3, 171.9, 168.8, 142.6, 139.6, 128.8, 127.6,
126.7, 125.5, 124.6, 115.1, 56.0, 45.1, 40.8, 20.6 ppm;
ESI (?) MS: m/z = 522 ([M ? H]?), 544 ([M ? Na]?),
1064 ([2 M - H ? Na]?); ESI (-) MS: m/z = 520
([M - H]-).
d = 1.3 (t, 3H, CH3, J = 7.2), 2.6 (s, 3H, CH3), 3.4 (s, 2H,
C11-H, C12-H), 4.3 (q, 2H, CH2, J = 7.2), 4.9 (s, 2H, C9-H,
C10-H), 7.1–7.9 (m, 12H, Ar H), 11.1 (br, 1H, NH) ppm;
13C NMR (100 MHz, DMSO-d6): d = 171.1, 169.6, 165.8,
150.1, 142.3, 139.9, 128.6, 127.4, 126.8, 125.5, 124.7,
102.1, 60.9, 45.1, 40.8, 21.3, 14.7 ppm.
2-[4-Phenyl-5-(phenylazo)thiazol-2-yl]-2,3,4a,5,10,10a-
hexahydro-5,10-benzenobenzo[g]phthalazine-1,4-dione
(4h, C33H23N5O2S)
2-[5-(4-Chlorophenylazo)-4-methylthiazol-2-yl]-
2,3,4a,5,10,10a-hexahydro-5,10-benzenobenzo[g]-
phthalazine-1,4-dione (4d, C28H20ClN5O2S)
Crystallization from EtOH-benzene afforded 1.938 g
(70%) 4h, orange. M.p.: 287 °C; IR (KBr): v = 3,360
Crystallization from DMF-MeOH afforded 2.183 g (83%)
4d, orange. M.p.: 286 °C; IR (KBr): v = 3,250 (NH),
(NH), 1,734 (CO), 1,528 (N=N) cm-1 1H NMR
;
(200 MHz, DMSO-d6): d = 3.3 (s, 2H, C11-H, C12-H),
4.8 (s, 2H, C9-H, C10-H), 7.2–7.6 (m, 18H, Ar–H), 11.3 (s,
1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 173.2, 171.4, 170.1, 169.4, 150.3, 142.5, 139.6,
130.0, 129.0, 129.8, 127.4, 127.2, 126.8, 125.6, 125.0,
124.7, 124.6, 105.1, 45.2, 40.8 ppm.
1,712 (CO), 1,508 (N=N) cm-1 1H NMR (200 MHz,
;
DMSO-d6): d = 2.3 (s, 3H, CH3), 3.3 (s, 2H, C11-H, C12-
H), 4.9 (s, 2H, C9-H, C10-H), 7.0–7.9 (m, 12H, Ar–H),
12.2 (s, 1H, NH) ppm; 13C NMR (100 MHz, DMSO-d6):
d = 173.1, 171.3, 168.7, 148.5, 141.1, 139.0, 134.5, 130.0,
123