1088
Sigmundová, Zahradník, Loos:
16.34% S; foun d: 54.85% C, 5.05% H, 7.25% N, 16.44% S. 1H NMR (300 MHz, DMSO-d6):
8.28 d, 1 H, J(7,6) = 8.1 (H-7); 8.09 d, 1 H, J(4,5) = 8.4 (H-4); 8.03 d, 1 H, J(trans) = 15.3
(H-b); 7.89 d, 2 H, J = 9.0 (H-2′, H-6′); 7.77 t, 1 H, J = 7.2 (H-5); 7.67 t, 1 H, J = 7.2 (H-6);
7.60 d, 1 H, J(trans) = 15.3 (H-a); 6.80 d, 2 H, J = 9.0 (H-3′, H-6′); 4.22 s, 3 H (CH3); 3.08 s,
6 H (2 × CH3). 13C NMR (75 MHz, DMSO-d6): 171.31 (C-2); 153.43 (C-4′); 150.08 (CH-b);
141.92 (C-3a); 132.81 (C-2′, C-6′); 128.85 (CH-5); 127.42 (CH-6); 126.80 (C-7a); 123.77
(CH-7); 121.44 (C-1′); 115.92 (CH-4); 111.91 (C-3′, C-5′); 106.24 (CH-a); 39.75 (N(CH3)2);
35.52 (N-CH3). UV/VIS (m eth an ol), λm ax (ε): 206 (38 300), 522 (71 500).
2-{(E)-2-[4-(Dimethylamino)phenyl]vinyl}-3-methyl-5-nitrobenzothiazol-3-ium iodide (5d ). M.p.
242–243 °C. For C18H18IN3O2S (467.3) calculated: 46.26% C, 3.88% H, 8.99% N, 6.86% S;
foun d: 46.12% C, 3.85% H, 8.79% N, 6.75% S. 1H NMR (300 MHz, DMSO-d6): 8.82 d, 1 H,
J(4,6) = 1.9 (H-4); 8.52 d, 1 H, J(7,6) = 8.8 (H-7); 8.44 dd, 1 H, J(6,7) = 8.8, J(6,4) = 1.9 (H-6);
8.12 d, 1 H, J(trans) = 15.2 (H-b); 7.96 d, 2 H, J = 8.9 (H-2′, H-6′); 7.59 d, 1 H, J(trans) = 15.2
(H-a); 6.81 d, 2 H, J = 9.0 (H-3′, H-6′); 4.26 s, 3 H (CH3); 3.12 s, 6 H (2 × CH3). 13C NMR
(75 MHz, DMSO-d6): 173.50 (C-2); 154.10 (C-4′); 152.13 (CH-b); 147.55 (C-5); 142.44 (C-3a);
133.66 (C-2′, C-6′); 133.51 (CH-7a); 125.00 (CH-7); 121.52 (C-6); 121.40 (C-1′); 112.15 (C-3′,
C-5′); 111.00 (CH-4); 105.54 (CH-a); 48.55 (N(CH3)2); 35.86 (N-CH3). UV/VIS (m eth an ol),
λm ax (ε): 548 (58 800). UV/VIS (CHCl3), λm ax (ε): 282 (6 700), 576 (42 600).
2-{(E)-2-[3-(Dimethylamino)phenyl]vinyl}-3-methyl-5-nitrobenzothiazol-3-ium iodide (5e). M.p.
224–225 °C. For C18H18IN3O2S (467.3) calculated: 46.26% C, 3.88% H, 8.99% N, 6.86% S;
foun d: 46.05% C, 3.81% H, 8.69% N, 6.84% S. 1H NMR (300 MHz, DMSO-d6): 9.10 d, 1 H,
J(4,6) = 1.8 (H-4); 8.71 d, 1 H, J(7,6) = 8.7 (H-7); 8.61 dd, 1 H, J(6,7) = 8.7, J(6,4) = 1.8 (H-6);
8.30 d, 1 H, J(trans) = 15.9 (H-b); 8.02 d, 1 H, J(trans) = 15.9 (H-a); 7.42–7.35 m , 3 H (H-Ar);
7.00–6.96 m , 1 H (H-Ar); 4.47 s, 3 H (CH3); 3.00 s, 6 H (2 × CH3). 13C NMR (75 MHz,
DMSO-d6): 175.64 (C-2); 151.96 (CH-b); 150.62 (C-3′); 147.91 (C-5); 142.41 (C-3a); 134.43,
134.21 (CH-7a, C-1′); 129.79 (CH-5′); 125.84 (CH-7); 122.52 (CH-6); 118.27, 117.10 (CH-a,
CH-6′); 113.55 (CH-2′); 113.42 (CH-4′); 112.62 (CH-4); 40.17 (N(CH3)2); 37.10 (N-CH3).
UV/VIS (m eth an ol), λm ax (ε): 206 (30 900), 218 (32 600), 256 (22 400), 272 (21 800), 384
(20 600).
2-{(E)-2-[2-(Dimethylamino)phenyl]vinyl}-3-methyl-5-nitrobenzothiazol-3-ium iodide (5f). M.p.
213–214 °C. For C18H18IN3O2S (467.3) calculated: 46.26% C, 3.88% H, 8.99% N, 6.86% S;
foun d: 46.15% C, 3.79% H, 8.72% N, 6.77% S. 1H NMR (300 MHz, DMSO-d6): 9.09 d, 1 H,
J(4,6) = 1.8 (H-4); 8.64 d, 1 H, J(7,6) = 9.0 (H-7); 8.59 dd, 1 H, J(6,7) = 9.0, J(6,4) = 1.8 (H-6);
8.38 d, 1 H, J(trans) = 16.1 (H-b); 8.09 dd, 1 H, J(6′,5′) = 7.5, J(6′,4′) = 1.5 (H-6′); 8.09 d, 1 H,
J(trans) = 15.9 (H-a); 7.55 dt, 1 H, J(4′,5′,6′) = 7.8, J(4′,6′) = 1.5 (H-4′); 7.26–7.16 m , 2 H (H-3′,
H-5′); 4.43 s, 3 H (CH3); 2.87 s, 6 H (2 × CH3). 13C NMR (75 MHz, DMSO-d6): 175.94 (C-2);
155.11 (C-2′); 147.92 (CH-b); 147.45 (C-5); 142.49 (C-3a); 133.93 (C-7a); 133.83 (CH-4′);
129.84 (C-1′); 125.98, 125.66 (CH-7, CH-6′); 122.53, 122.20 (CH-6, CH-5′); 119.09 (CH-3′);
112.53, 112.51 (CH-4, CH-a); 45.27 (N(CH3)2); 36.83 (N-CH3). UV/VIS (m eth an ol), λm ax (ε):
268 (17 000), 368 (18 400), 464 (8 700).
2-{(E)-2-[4-(Dimethylamino)phenyl]vinyl}-3-methyl-6-nitrobenzothiazol-3-ium iodide (5g). M.p.
255–258 °C. For C18H18IN3O2S (467.3) calculated: 46.26% C, 3.88% H, 8.99% N, 6.86% S;
foun d: 46.29% C, 3.85% H, 8.98% N, 6.52% S. 1H NMR (300 MHz, DMSO-d6): 9.28 d, 1 H,
J(7,5) = 1.2 (H-7); 8.56 dd, 1 H, J(5,4) = 8.8, J(5,7) = 1.2 (H-5); 8.26 d, 1 H, J(4,5) = 9.0 (H-4);
8.22 d, 1 H, J(trans) = 15.1 (H-b); 7.99 d, 2 H, J = 8.5 (H-2′, H-6′); 7.62 d, 1 H, J(trans) = 15.1
(H-a); 6.89 d, 2 H, J = 8.5 (H-3′, H-6′); 4.23 s, 3 H (CH3); 3.19 s, 6 H (2 × CH3). 13C NMR
(75 MHz, DMSO-d6): 174.32 (C-2); 154.26 (C-4′); 152.57 (CH-b); 145.98 (C-3a); 145.22
Collect. Czech. Chem. Commun. 2007, Vol. 72, No. 8, pp. 1069–1093