Month 2017
A New Route for Synthesis of 2-Substituted-3-amino-5-phenyl-7-N,N-
dimethylamino Phenazinium Chloride Salts
1
1
3
6
43.8, 142.6, 141.9, 131.5, 131.2, 130.7, 130.2, 129.1,
2-amino-3-amino-5-phenyl-7-N,N-dimethylamino
phenazinium chloride (3 h).
IR (KBr thin film): 3400,
838, 2717, 2160, 1635, 1598, 1521, 1235, 1515, 1135,
28.8, 127.5, 120.8, 36.5, 34.5, 31.2; MS (ESI): m/z
+
2
72(M +H) ; Anal. Calcd for C H N Cl: C, 70.85; H,
2
4 27 4
À1
1
.64; N, 13.78. Found: C, 70.70; H,6.57; N, 13.67.
775, 624 cm ; UV(MeOH): λmax= 542.00nm. HNMR
(
500 MHz, DMSO-d ) 3.04 (-(CH ) N), 3.26(-H NAr),
2
-Chloro-3-amino-5-phenyl-7-N,N-dimethylamino
6 3 2 2
3
.31(-H NAr), 6.62(-aryl CH), 6.92(-aryl CH), 7.02(-aryl
2
phenazinium chloride (3d).
IR (KBr thin film): 3400,
838, 2717, 2160, 1630, 1598, 1521, 1135, 1095,775,
24cm
13
2
6
CH),7.65~ 8.50(-aryl CH); C NMR (75 MHz, CDCl
DMSO-d ) δ: 144.8, 143.2, 142.9, 142.2, 141.9, 141.3,
3
À1
1
+
;
UV(MeOH): λmax = 542.00 nm. HNMR
6
1
40.5, 139.8, 130.7, 129.4, 127.9, 126.6, 124.2, 123.6,
(500 MHz, DMSO-d ) 2.85(-(CH ) N), 3.47(H NAr),5.12
6 3 2 2
+
(-aryl CH), 5.52 (-aryl CH), 6.24(-aryl CH),7.84~ 8.72(-
122.7, 118.8, 33.9; MS (ESI): m/z 331 (M + H) ; Anal.
Calcd for C H N Cl: C, 65.66; H, 5.47; N, 19.15.
13
aryl CH); C NMR (75 MHz, CDCl +DMSO-d ) δ:
20 20 5
3
6
Found: C, 65.77; H, 5.39;N, 19.12.
1
1
3
47.1, 146.6, 145.3, 144.8, 144.2, 143.6, 142.5, 131.8,
30.2, 129.9, 129.2, 128.4, 127.3, 126.6, 125.4, 124.7,
2.5; MS (ESI): m/z 350.5 (M +H) ; Anal. Calcd for
2-methylamino-3-amino-5-phenyl-7-N,N-dimethylamino
phenazinium chloride (3i). IR (KBr thin film): 3450, 2838,
+
C H N Cl : C, 62.33; H, 4.93; N, 14.55. Found: C,
2717, 2160, 1635, 1598, 1521, 1450, 1375, 1135, 775,
20
18
4
2
À1
1
6
2.61; H, 5.08;N, 14.4016.10; Cl, 10.21.
624 cm
;
UV(MeOH):
λmax =542.00nm. HNMR
(
500 MHz, DMSO-d ), 2.63(-CH NH), 3.04(-(CH ) N),
2
-bromo-3-amino-5-phenyl-
7-N,N-dimethylamino
6
3
3 2
phenazinium chloride (3e).
IR(KBr thin film): 3400,
3.25(-H
2
NAr),3.56(-NHCH ), 6.49(-aryl CH), 6.58(aryl
3
13
2
838, 2717, 2160, 1630, 1598, 1521, 1135, 775,
CH), 7.12(-aryl CH), 7.75 ~8.50(-aryl CH); C NMR
(75 MHz, CDCl +DMSO-d ) δ: 145.5, 145.1, 144.7,
143.8, 142.6, 141.9, 141.3, 140.8, 132.5, 131.9, 130.6,
À1
6
24,575 cm
;
UV(MeOH):
λmax = 542.00 nm.
3
6
1
HNMR(500MHz, DMSO-d ) 3.02 (-(CH ) N), 3.41(-
6
3 2
H NAr),5.55 (-aryl CH), 5.83 6.28(-aryl CH), (-aryl
128.2, 127.6, 125.7, 122.4, 117.3, 37.9, 32.2; MS (ESI):
2
1
3
+
CH),7.75 ~8.73(-aryl CH); C NMR (75 MHz, CDCl3
DMSO-d ) δ: 147.6, 147.1, 146.8, 146.2, 145.3, 144.8,
m/z 345(M + H) ; Anal. Calcd for C21
H
N
22
Cl: C, 66.40;
5
+
H, 5.80; N, 18.45. Found: C, 66.29; H, 5.86; N, 18.25.
6
1
1
43.9, 141.9, 131.3, 130.8, 130.1, 129.7, 128.4, 127.8,
27.1, 126.6, 35.5; MS (ESI): m/z 395(M + H) ; Anal.
2-ethylamino-3-amino-5-phenyl-
phenazinium chloride (3j). Greenish solid, mp > 300°C;
7-N,N-dimethylamino
+
Calcd for C H N BrCl: C, 55.88; H, 4.19; N, 13.04.
Found: C, 55.91; H, 4.25; N, 12.89.
IR(KBr thin film): 3400, 2838, 2717, 2160, 1630, 1598,
20 18 4
À1
1521, 1465, 1450, 1375, 1250, 1135, 775, 624cm
;
1
UV(MeOH):
DMSO-d
3.09(-CH
6.63 (-aryl CH), 6.91(-aryl CH),7.19(-aryl CH), 7.45 ~8.20
λmax =542.00nm. HNMR(500MHz,
δ:1.19(-CH CH NH), 3.04 (-(CH N),
NH), 3.22(-H NAr), 3.35-NHCH CH ),
2
-hydroxy-3-amino-5-phenyl-7-N,N-dimethylamino
phenazinium chloride (3f). IR (KBr thin film):3610,3400,
6
)
3
2
)
3 2
2
6
838, 2717, 2160, 1630, 1598, 1521, 1200, 1135, 775,
CH
3
2
2
2
3
À1
1
24cm
;
UV(MeOH): λmax = 542.00 nm. HNMR
13
(
500 MHz, DMSO-d ) δ: 3.05 (-(CH ) N), 3.37 (-H NAr),
(-aryl CH); C NMR (75 MHz, CDCl + DMSO-d ) δ:
3 6
6
3 2
2
5
6
.23 (-aryl OH), 5.67 (-aryl CH), 5.95 (-aryl CH),
.24(-aryl CH),7.59~ 8.56 (-aryl CH); C NMR (75 MHz,
148.2, 147.3, 146.7, 145.8, 145.2, 144.5, 143.8, 142.1,
130.7, 128.8, 127.6, 126.9, 125.8., 118.3, 117.8, 116.8,
38.2, 31.7, 15.6; MS (ESI): m/z 359(M +H) ; Anal. Calcd
1
3
+
CDCl + DMSO-d ) δ: 149.5, 148.8, 147.4, 146.6, 145.2,
3
6
1
1
43.5, 142.1, 141.3, 133.2, 132.0, 131.3, 130.4, 129.8,
28.3, 127.9, 127.2, 35.8; MS (ESI): m/z 332(M +H) ;
for C22H N Cl: C, 67.09; H, 6.10; N, 17.79. Found: C,
67.21; H, 6.02; N, 17.85.
24 5
+
Anal. Calcd for C H N OCl: C, 65.48; H, 5.18; N, 15.28;
O,4.37. Found: C, 65.65; H, 5.01;N, 15.08; O,4.26.
2-dimethylamino-3-amino-5-phenyl-7-N,N-dimethylamino
phenazinium chloride (3 k). IR (KBr thin film):3400, 3325,
2
0 19 4
2
838, 2717, 2160, 1630, 1598, 1521, 1450, 1375, 1135, 775,
2
-hydroxyethyl-3-amino-5-phenyl-7-N,N-dimethylamino
À1
phenazinium chloride (3 g). IR (KBr thin film): 3400,
838, 2717, 2160, 1630, 1598, 1521, 1135, 1050,775,
24cm
500 MHz,
.89(-CH CH ),
.84(-CH CH )5.62 (-aryl CH), 5.92(-aryl CH), 6.15
-aryl CH), 7.67~ 8.55(-aryl CH); C NMR (75 MHz,
CDCl + DMSO-d ) δ: 146.7, 146.4, 145.9, 145.1, 144.8,
624 cm
;
UV
(MeOH):
) δ: 2.65~3.04 (-(CH
NAr), 6.50 (-aryl CH), 6.85(-aryl CH), 7.25(-aryl
λmax =542.00nm.
1
2
6
(
2
3
(
HNMR(500 MHz, DMSO-d
3.24(-H
CH),7.37~ 8.43(-aryl CH);
CDCl + DMSO-d ) δ: 147.2, 146.3, 145.8, 144.6, 143.9,
6
3 2
)
N),
À1
1
;
UV(MeOH): λmax = 542.00 nm. HNMR
2
13
DMSO-d6)
δ:2.05
(HOCH CH -),
C
NMR (75 MHz,
2
2
3.06
(-(CH ) N),
3.31(-H NAr),
3
6
2
2
3 2
2
143.2, 142.6, 141.3, 132.6, 130.9, 127.2, 125.1, 124.4,
122.7, 119.5, 112.6, 31.8, 30.6;MS (ESI): m/z 359(M
+ H) ; Anal. Calcd for C22
2
2
1
3
+
H
24
N
Cl: C, 67.09; H, 6.10; N,
5
3
6
1
1
43.2, 142.7, 141.5, 133.4, 132.5, 131.2, 130.8, 129.9,
17.79. Found: C, 66.91; H, 6.22; N, 17.55.
28.8, 127.8, 126.4, 64.2, 41.3, 32.5; MS (ESI): m/z 360
2-cyano-3-amino-5-phenyl-7-N,N-dimethylamino
+
(M + H) ; Anal. Calcd for C H N OCl: C, 66.92; H,
phenazinium chloride (3 l).
IR (KBr thin film): 3400,
2
2 23 4
5
1
.83; N, 14.20; O, 4.06. Found: C, 66.79; H, 5.62; N,
4.01; O, 4.13.
2838, 2717, 2230, 2160, 1630, 1598, 1521, 1135, 775,
À1
1
624 cm
;
UV(MeOH): λmax = 542.00 nm. HNMR
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet