IIIA.6

(2-Benzo[d]thiazol-2-yl-phenyl)-phenyl-methanone (1a):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.12 (d, 1H, J = 7.6 Hz), 7.92 (d, 1H, J = 7.2 Hz), 7.79 (d, 1H, J = 8.4 Hz), 7.76 (d, 1H, 7.6 Hz), 7.64−7.57 (m, 2H), 7.54 (d, 1H, J = 6.8 Hz), 7.47 (t, 2H, J = 7.6 Hz), 7.39−7.32 (m, 2H), 7.31−7.25 (m, 2H); ¹³C NMR (CDCl3, 100 MHz): δ 197.7, 165.6, 153.4, 139.7, 137.8, 135.3, 133.8, 132.8, 132.1, 130.4, 130.3, 129.4, 128.5, 128.3, 126.3, 125.4, 123.4, 121.5; IR (KBr, cm^-1): 3060, 2923, 2849, 2725, 2553, 1686, 1667, 1596, 1580, 1450, 1427, 1316, 1283, 1255, 1179, 1154, 1126, 1026, 968, 923, 759; HRMS (ESI) calcd for C20H13NOS (M + H⁺) 316.0791, found 316.0790.

(2-Benzo[d]thiazol-2-yl-phenyl)-(4-methoxy-phenyl)-methanone (1b):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.05 (d, 1H, J = 9.2 Hz), 7.94 (d, 1H, J = 7.2 Hz), 7.82 (d, 1H, J = 7.8 Hz), 7.78−7.72 (m, 2H), 7.61−7.54 (m, 2H), 7.47 (d, 1H, J = 6.8 Hz), 7.37−7.33 (m, 1H), 7.30−7.26 (m, 1H), 6.93 (d, 1H, J = 8.4 Hz), 6.77 (d, 1H, J = 8.0 Hz), 3.85 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 197.5, 164.2, 163.5, 153.7, 140.2, 135.6, 132.5, 132.0, 130.9, 130.3, 130.1, 129.9, 128.6, 126.3, 125.4, 123.6, 121.6, 113.8, 55.5; IR (KBr, cm^-1): 2934, 2840, 2541, 1662, 1601, 1577, 1510, 1427, 1303, 1259, 1167, 1149, 1026, 965, 928, 844, 761; Anal.

calcd for C₂₁H₁₅NO₂S: C 73.02, H 4.38, N 4.06; found: C 73.07, H 4.44, N 4.03.

(2-(Benzo[d]thiazol-2-yl)phenyl)(4-butoxyphenyl)methanone (1c):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 7.96 (d, 1H, J = 7.4 Hz), 7.84 (d, 1H, J = 8.0 Hz), 7.79 (d, 1H, J = 7.6 Hz), 7.74 (d, 2H, J = 8.8 Hz), 7.62−7.56 (m, 2H), 7.49 (d, 1H, J = 7.2 Hz), 7.38 (t, 1H, J = 8.0 Hz), 7.30 (t, 1H, J = 7.6 Hz), 6.72 (d, 2H, J = 10.0 Hz), 3.93 (t, 2H, J = 6.4 Hz), 1.75−1.70 (m, 2H), 1.53−1.48 (m, 2H), 0.90−0.85 (m, 3H); ¹³C NMR (CDCl₃, 100 MHz): δ 196.3, 165.7, 163.2, 153.6, 140.2, 135.6, 132.4, 131.9, 130.5, 130.2, 130.0, 129.9, 128.5, 126.2, 125.4, 123.6, 121.6, 114.3, 68.1, 31.2, 19.2, 13.9; IR (KBr, cm^-1): 3060, 2958, 2929, 2871, 1655, 1599, 1561, 1509, 1465, 1434, 1381, 1311, 1255, 1176, 1150, 1068, 1026, 966, 928, 844, 762; Anal. calcd for C₂₄H₂₁NO₂S: C 74.39, H 5.46, N 3.61; found: C 74.45, H 5.52, N 3.55.

(2-Benzo[d]thiazol-2-yl-phenyl)-p-tolyl-methanone (1d):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 7.94 (d, 1H, J = 7.4 Hz), 7.81 (d, 1H, J = 8.2 Hz), 7.78 (d, 1H, J = 8.4 Hz), 7.67 (d, 2H, J = 8.0 Hz), 7.63−7.56 (m, 2H), 7.49 (d, 1H, J = 7.6 Hz), 7.36 (t, 1H, J = 7.6 Hz), 7.29 (t, 1H, J = 7.5 Hz), 7.10 (d, 2H, J = 8.0 Hz), 2.29 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 197.5, 165.6, 153.7, 143.8, 140.2, 135.6, 135.4, 132.2, 130.4, 130.2, 129.9, 129.7, 129.2, 128.9, 126.3, 125.4, 123.7, 121.6, 21.8; IR (KBr, cm^-1):

2967, 2850, 2772, 1638, 1510, 1479, 1458, 1432, 1313, 1224, 1071, 964, 766; HRMS (ESI) calcd for C₂₁H₁₅NOS (M + H⁺) 330.0947, found 330.0943.

(2-Benzo[d]thiazol-2-yl-phenyl)-(4-biphenyl)-methanone (1e):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 7.96 (d, 1H, J = 7.2 Hz), 7.85−7.82 (m, 2H), 7.80−7.77 (m, 2H), 7.66−7.59 (m, 2H), 7.56−7.50 (m, 4H), 7.42−7.38 (m,

2H), 7.37−7.32 (m, 2H), 7.30−7.25 (m, 2H); ¹³C NMR (CDCl₃, 100 MHz): δ 197.3, 165.5, 153.7, 145.5, 140.1, 139.9, 136.7, 135.5, 132.2, 130.5, 130.3, 130.1, 129.9, 129.0, 128.9, 128.3, 127.4, 127.1, 126.3, 125.5, 123.6, 121.6; IR (KBr, cm^-1): 3057, 3027, 2961, 2923, 2846, 1666, 1601, 1483, 1432, 1403, 1312, 1262, 1152, 1060, 966, 929, 855, 759; HRMS (ESI) calcd for C₂₆H₁₇NOS (M + H⁺) 392.1104, found 392.1104.

(2-Benzo[d]thiazol-2-yl-phenyl)-(3-fluoro-phenyl)-methanone (1f):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 7.92 (d, 1H, J = 8.4 Hz), 7.79 (d, 1H, J = 7.2 Hz), 7.76 (d, 1H, J = 8.0 Hz), 7.67−7.59 (m, 2H), 7.54 (d, 1H, J = 7.6 Hz), 7.50−7.48 (m, 2H), 7.36 (t, 1H, J = 7.1 Hz), 7.31 (t, 1H, J = 7.4 Hz), 7.26−7.22 (m, 1H), 7.08−7.04 (m, 1H); ¹³C NMR (CDCl3, 100 MHz): δ 196.4, 164.2, 163.9, 153.5, 140.3, 139.2, 135.2, 132.1, 130.6, 130.0, 129.9, 129.7, 129.0, 126.4, 125.6, 125.0, 123.5, 121.6, 119.8, 119.6, 115.8, 115.5; IR (KBr, cm^-1): 3068, 2919, 2844, 2360, 2341, 1668, 1607, 1586, 1505, 1479, 1446, 1434, 1286, 1258, 1123, 1069, 970, 888, 836, 801, 772, 760; Anal. calcd for C₂₀H₁₂FNOS: C 72.05, H 3.63, N 4.20; found: C 72.10, H 3.67, N 4.15.

(2-( Benzo[d]thiazol-2-yl)phenyl)(2-chlorophenyl)methanone (1g):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 7.98 (d, 1H, J = 8.0 Hz), 7.81−7.75 (m, 2H), 7.71 (d, 1H, J = 5.8 Hz), 7.66−7.59 (m, 2H), 7.40 (t, 1H, J = 7.6 Hz), 7.35−7.29 (m, 2H), 7.19 (d, 1H, J = 8.0 Hz), 7.09 (t, 1H, J = 7.7 Hz), 6.99 (t, 1H, J = 7.6 Hz); ¹³C NMR (CDCl3, 100 MHz): δ 195.8, 165.6, 153.6, 139.9, 137.5, 135.6, 133.2, 133.0, 131.9, 131.3, 131.1, 130.9, 130.6, 130.4, 130.1, 126.3, 126.1, 125.5, 123.9, 121.5; IR (KBr, cm^-1): 3060, 2923,

1672, 1585, 1502, 1468, 1453, 1430, 1312, 1296, 1253, 1170, 1061, 1036, 1012, 968, 930, 856, 767, 758; Anal.

calcd for C20H12ClNOS: C 68.67, H 3.46, N 4.00; found:

C 68.72, H 3.50, N 3.95.

(2- Benzo[d]thiazol-2-yl-phenyl)-(3-chloro-phenyl)-methanone (1h):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 7.91 (d, 1H, J = 7.2 Hz), 7.79 (d, 2H, J = 8.6 Hz), 7.75 (d, 1H, J = 5.2 Hz), 7.66−7.57 (m, 3H), 7.53 (d, 1H, J = 8.0 Hz), 7.37 (t, 1H, J

= 7.4 Hz), 7.32−7.28 (m, 2H), 7.19 (t, 1H, J = 7.8 Hz);

13C NMR (CDCl3, 100 MHz): δ 196.3, 165.2, 153.4, 139.7, 139.0, 135.2, 134.5, 132.5, 132.1, 130.7, 130.6, 129.7, 129.6, 128.9, 128.3, 127.3, 126.4, 125.6, 123.4, 121.6; IR (KBr, cm^-1): 3059, 2928, 2854, 1669, 1590, 1570, 1507, 1482, 1431, 1281, 1255, 1242, 1156, 1073, 967, 897, 850, 807, 753; Anal. calcd for C20H12ClNOS: C 68.67, H 3.46, N 4.00; found: C 68.73, H 3.53, N 3.97.

(2-Benzo[d]thiazol-2-yl-phenyl)-(4-chloro-phenyl)-methanone (1i):

White solid; M.p. 135.5 ^oC; ¹H NMR (CDCl3, 400 MHz):

δ 7.93 (d, 1H, J = 6.8 Hz), 7.82−7.79 (m, 1H), 7.77−7.75 (m, 1H), 7.70−7.66 (m, 2H), 7.64−7.59 (m, 2H), 7.51 (d, 1H, J = 6.8 Hz), 7.39−7.35 (m, 1H), 7.34−7.29 (m, 1H), 7.27−7.24 (m, 2H); ¹³C NMR (CDCl3, 100 MHz): δ 196.5, 165.2, 153.6, 139.4, 139.1, 136.5, 135.4, 132.1, 130.7, 130.5, 129.8, 128.9, 128.8, 126.5, 125.7, 123.6, 121.6; IR (KBr, cm^-1): 3088, 3055, 2956, 2923, 2845, 1670, 1584, 1571, 1483, 1428, 1401, 1304, 1288, 1263, 1240, 1181, 1151, 1090, 1013, 968, 936, 923, 844, 753;

Anal. calcd for C20H12ClNOS: C 68.67, H 3.46, N 4.00;

found: C 68.74, H 3.51, N 3.96.

(2-Benzo[d]thiazol-2-yl-phenyl)-(4-carboxymethyl-phenyl)-methanone (1j):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 7.93 (d, 2H, J = 8.6 Hz), 7.79−7.77 (m, 3H), 7.73−7.71 (m, 1H), 7.68−7.61 (m, 3H), 7.58−7.56 (m, 1H), 7.45 (t, 1H, J = 7.4 Hz), 7.29 (t, 1H, J = 7.3 Hz), 3.86 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 197.1, 166.5, 165.1, 153.5, 141.6, 139.3, 135.2, 133.3, 130.8, 129.7, 129.6, 129.2, 128.9, 126.5, 125.7, 123.5, 121.7, 52.5; IR (KBr, cm^-1): 2955, 2920, 2847, 1717, 1674, 1500, 1434, 1406, 1279, 1104, 1015, 970, 928, 865, 757; Anal. calcd for C22H15NO3S: C 70.76, H 4.05, N 3.75; found: C 70.80, H 4.08, N 3.70.

(2-(Benzo[d]thiazol-2-yl)phenyl)(3-nitrophenyl)methanone (1k):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.51 (s, 1H), 8.17 (d, 1H, J = 8.2 Hz), 8.06 (d, 1H, J = 7.6 Hz), 7.94 (d, 1H, J = 7.6 Hz), 7.78 (d, 1H, J = 7.6 Hz), 7.73−7.66 (m, 3H), 7.60 (d, 1H, J = 7.2 Hz), 7.49 (t, 1H, J = 8.0 Hz), 7.37−7.29 (m, 2H); ¹³C NMR (CDCl3, 100 MHz): δ 195.5, 164.9, 153.4, 148.2, 139.9, 138.3, 135.1, 134.3, 132.1, 131.3, 131.0, 129.8, 129.5, 129.3, 126.7, 126.6, 125.9, 123.6, 123.4, 121.7; IR (KBr, cm^-1): 3077, 3056, 2919, 2858, 1679, 1610, 1524, 1433, 1346, 1315, 1294, 1276, 1258, 1160, 1070, 970, 934, 855, 810, 755; Anal.

calcd for C₂₀H₁₂N₂O₃S: C 66.65, H 3.36, N 7.77; found: C 66.68, H 3.40, N 7.70.

(2-(Benzo[d]thiazol-2-yl)phenyl)(4-nitrophenyl)methanone (1l):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 8.09 (d, 2H, J = 8.8 Hz), 7.94 (d, 1H, J = 6.6 Hz), 7.87 (d, 2H, J = 8.8 Hz), 7.79 (d, 1H, J = 7.4 Hz), 7.72−7.65 (m, 3H), 7.59 (d, 1H, J = 6.6 Hz), 7.37 (d, 1H, J = 7.2 Hz), 7.34−7.29 (m, 1H);

13C NMR (CDCl3, 100 MHz): δ 196.0, 164.9, 153.3, 149.8, 143.2, 138.6, 135.1, 132.2, 131.2, 131.0, 129.7,

S N O

O₂N

129.3, 126.7, 126.0, 123.6, 123.4, 121.8; IR (KBr, cm^-1):

3099, 3067, 2847, 1703, 1673, 1602, 1519, 1454, 1428, 1382, 1342, 1318, 1283, 1196, 1103, 1007, 974, 930, 849, 816, 761; Anal. calcd for C20H12N2O3S: C 66.65, H 3.36, N 7.77; found: C 66.70, H 3.42, N 7.72.

(2-(Benzo[d]thiazol-2-yl)phenyl)(3,4-dimethoxyphenyl)methanone (1m):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.10−8.08 (m, 3H), 7.93 (d, 1H, J = 8.0 Hz), 7.52−7.47 (m, 3H), 7.41−7.38 (m, 3H), 7.03 (s, 1H), 4.02 (s, 3H), 3.92 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 196.2, 164.2, 153.7, 150.7, 144.7, 135.6, 131.4, 130.4, 129.9, 129.6, 129.4, 129.2, 126.9, 126.7, 125.1, 124.1, 123.4, 122.7, 116.1, 112.1; IR (KBr, cm^-1): 3060, 2961, 2900, 2867, 1668, 1603, 1510, 1459, 1432, 1407, 1314, 1266, 1192, 1106, 1015, 966, 930, 850, 760; Anal. calcd for C22H17NO3S: C 70.38, H 4.56, N 3.73; found: C 70.40, H 4.61, N 3.70.

(2-Benzo[d]thiazol-2-yl-phenyl)-(2,6-dichloro-phenyl)-methanone (1n):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 8.08 (d, 1H, J = 7.6 Hz), 7.83 (d, 1H, J = 8.0 Hz), 7.78 (d, 1H, J = 8.0 Hz), 7.72−7.66 (m, 2H), 7.62−7.58 (m, 1H), 7.50−7.45 (m, 1H), 7.40−7.33 (m, 2H), 7.14 (d, 1H, J = 8.0 Hz), 7.05 (t, 1H, J = 8.0 Hz); ¹³C NMR (CDCl3, 100 MHz): δ 191.9, 166.7, 153.3, 137.5, 136.8, 136.5, 135.1, 133.0, 132.8, 131.9, 131.7, 130.6, 130.5, 128.6, 128.4, 126.2, 125.4, 123.8, 121.5; IR (KBr, cm^-1): 3064, 2953, 2923, 2852, 1735, 1680, 1647, 1580, 1516, 1430, 1368, 1258, 1194, 1090, 966, 926, 806, 761; MS (ESI) calcd for C20H11Cl2NOS (M + H⁺) 384.0011, found 384.0019.

(2-(Benzo[d]thiazol-2-yl)phenyl)(4-chloro-3-nitrophenyl)methanone (1o):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 8.36 (s, 1H), 8.03 (d, 1H, J = 8.4 Hz), 7.94 (d, 1H, J = 7.0 Hz), 7.85−7.81 (m, 1H), 7.75 (d, 1H, J = 8.4 Hz), 7.71−7.64 (m, 2H), 7.56−7.54 (m, 1H), 7.45 (d, 1H, J = 8.4 Hz), 7.40−7.33 (m, 2H); ¹³C NMR (CDCl₃, 100 MHz): δ 194.3, 164.8, 153.2, 147.8, 138.1, 137.7, 135.5, 134.9, 132.9, 132.5, 132.0, 131.0, 129.7, 129.0, 126.7, 126.4, 125.9, 125.5, 123.3, 121.8; IR (KBr, cm^-1): 3097, 3067, 3031, 2856, 2731, 2360, 2341, 1703, 1676, 1599, 1567, 1536, 1431, 1356, 1295, 1238, 1201, 1049, 968, 918, 830, 817, 762; HRMS (ESI) calcd for C20H11ClN2O3S (M + H⁺) 395.0252, found 395.0257.

(2-Benzo[d]thiazol-2-yl-phenyl)-naphthalen-2-yl-methanone (1p):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.08 (s, 1H), 8.05 (d, 1H, J = 7.8 Hz), 7.99 (d, 1H, J = 6.6 Hz), 7.82−7.71 (m, 5H), 7.69−7.61 (m, 2H), 7.59−7.57 (m, 1H), 7.50 (t, 1H, J = 7.6 Hz), 7.43 (t, 1H, J = 7.1 Hz), 7.30 (t, 1H, J = 7.6 Hz), 7.25−7.22 (m, 1H); ¹³C NMR (CDCl3, 100 MHz): δ 197.8, 165.5, 153.6, 140.0, 135.6, 132.5, 132.3, 131.5, 130.5, 130.4, 129.9, 129.7, 129.0, 128.5, 127.9, 126.7, 126.3, 125.5, 124.9, 123.6, 121.5; IR (KBr, cm^-1): 3056, 3022, 2921, 2849, 1664, 1625, 1508, 1463, 1430, 1351, 1299, 1284, 1231, 1200, 1149, 1120, 968, 918, 869, 847, 827, 755; HRMS (ESI) calcd for C24H15NOS (M + H⁺) 366.0947, found 366.0941.

(2-Benzo[d]thiazol-2-yl-phenyl)-furan-2-yl-methanone (1q):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 7.93 (d, 1H, J = 7.2 Hz), 7.89 (d, 1H, J = 8.2 Hz), 7.83 (d, 1H, J = 7.8 Hz), 7.66−7.59 (m, 3H), 7.46−7.45 (m, 1H), 7.41 (t, 1H, J = 7.6 Hz), 7.34 (t, 1H, J = 7.4 Hz), 6.91 (d, 1H, J = 3.4 Hz),

6.36−6.34 (m, 1H); ¹³C NMR (CDCl3, 100 MHz): δ 184.7, 165.8, 153.8, 153.2, 147.1, 138.7, 135.6, 132.6, 130.9, 130.4, 130.1, 129.2, 126.4, 125.6, 123.8, 121.6, 119.4, 112.4; IR (KBr, cm^-1): 3060, 2950, 2922, 2851, 1657, 1566, 1512, 1462, 1432, 1390, 1308, 1226, 1186, 1151, 1079, 1019, 967, 889, 761; HRMS (ESI) calcd for C₁₈H₁₁NO₂S (M + H⁺) 306.0583, found 306.0588.

(2-Benzo[d]thiazol-2-yl-phenyl)-thiophen-2-yl-methanone (1r):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 7.96 (d, 1H, J = 7.2 Hz), 7.89 (d, 1H, J = 8.4 Hz), 7.82 (d, 1H, J = 8.0 Hz), 7.66−7.57 (m, 4H), 7.40 (t, 1H, J = 7.6 Hz), 7.33 (t, 1H, J

= 7.6 Hz), 7.27−7.26 (m, 1H), 6.92 (t, 1H, J = 4.4 Hz);

13C NMR (CDCl3, 100 MHz): δ 189.8, 165.5, 153.8, 145.3, 139.6, 135.7, 134.5, 132.1, 130.6, 130.4, 130.1, 128.8, 128.0, 126.4, 125.5, 123.8, 121.6; IR (KBr, cm^-1):

2964, 2921, 2850, 1642, 1512, 1432, 1411, 1354, 1298, 1262, 1100, 1042, 967, 841, 807, 761; HRMS (ESI) calcd for C₁₈H₁₁NOS₂ (M + H⁺) 322.0355, found 322.0354.

1-(2-Benzo[d]thiazol-2-yl-phenyl)-3-phenyl-propan-1-one (1s):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.02 (d, 1H, J = 8.4 Hz), 7.91 (d, 1H, J = 8.0 Hz), 7.82−7.79 (m, 1H), 7.53−7.47 (m, 2H), 7.43−7.39 (m, 1H), 7.38−7.35 (m, 1H), 7.19−7.15 (m, 2H), 7.12−7.03 (m, 2H), 7.02 (d, 2H, J = 7.2 Hz), 3.09 (t, 2H, J = 7.6 Hz), 2.97−2.93 (m, 2H);

13C NMR (CDCl₃, 100 MHz): δ 206.1, 166.1, 153.0, 141.9, 141.3, 135.5, 130.8, 130.3, 129.9, 128.7, 128.6, 128.5, 127.4, 126.8, 126.1, 125.9, 123.8, 121.9, 45.5, 30.9; IR (KBr, cm^-1): 3081, 3060, 3026, 3023, 2852, 1735, 1700, 1636, 1602, 1495, 1480, 1453, 1433, 1404,

HRMS (ESI) calcd for C₂₂H₁₇NOS (M + H⁺) 344.1104, found 344.1101.

(2-(Benzo[d]thiazol-2-yl)-5-methylphenyl)(phenyl)methanone (2a):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 7.82 (d, 1H, J = 8.0 Hz), 7.76−7.71 (m, 4H), 7.41 (d, 1H, J = 8.0 Hz), 7.38−7.33 (m, 3H), 7.30−7.24 (m, 3H), 2.46 (s, 3H); ¹³C NMR (CDCl₃, 100 MHz): δ 197.9, 165.6, 153.5, 141.0, 139.7, 137.9, 135.2, 133.7, 132.7, 130.9, 129.7, 129.4, 129.3, 128.3, 126.2, 125.2, 123.3, 121.4, 21.5; IR (KBr, cm^-1): 3053, 3024, 2920, 2855, 1669, 1597, 1561, 1511, 1476, 1449, 1432, 1400, 1315, 1287, 1256, 1208, 1177, 1116, 1073, 975, 957, 854, 826, 789, 757; Anal. calcd for C₂₁H₁₅NOS: C 76.57, H 4.59, N 4.25; found: C 76.62, H 4.63, N 4.22.

(2-Benzo[d]thiazol-2-yl-5-methoxy-phenyl)-phenyl-methanone (3a):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.03 (d, 2H, J = 8.0 Hz), 7.77 (d, 1H, J = 8.8 Hz), 7.69 (d, 1H, J = 8.4 Hz), 7.64 (t, 1H, J = 7.6 Hz), 7.51 (t, 1H, J = 7.4 Hz), 7.37 (t, 2H, J = 7.4 Hz), 7.29−7.24 (m, 1H), 7.22−7.16 (m, 1H), 7.02 (d, 1H, J = 8.4 Hz), 6.94 (s, 1H), 3.74 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 197.5, 165.3, 161.3, 153.5, 141.4, 137.7, 135.2, 133.9, 131.3, 130.3, 129.4, 128.6, 126.2, 125.1, 123.2, 121.4, 116.0, 114.1, 55.8; IR (KBr, cm^-1): 3071, 2963, 2916, 2834, 2676, 2558, 1687, 1602, 1583, 1453, 1424, 1326, 1292, 1179, 1099, 1072, 1026, 934, 807, 762; Anal. calcd for C21H15NO2S: C 73.02, H 4.38, N 4.06; found: C 73.05, H 4.40, N 4.01.

(2-(Benzo[d]thiazol-2-yl)-5-butoxyphenyl)(phenyl)methanone (4a):

White solid; M.p. 133 ^oC; ¹H NMR (CDCl₃, 400 MHz): δ 7.85 (d, 1H, J = 8.8 Hz), 7.78 (d, 2H, J = 7.6 Hz), 7.73 (t, 2H, J = 7.2 Hz), 7.38 (t, 1H, J = 7.2 Hz), 7.34−7.23 (m, 4H), 7.11 (d, 1H, J = 8.6 Hz), 7.01 (s, 1H), 4.05 (t, 2H, J

= 6.4 Hz), 1.82−1.77 (m, 2H), 1.53−1.48 (m, 2H), 0.98 (t, 3H, J = 7.6 Hz); ¹³C NMR (CDCl₃, 100 MHz): δ 197.5, 165.3, 160.9, 153.7, 141.4, 137.8, 135.2, 132.8, 131.3, 129.4, 128.4, 126.1, 125.0, 124.4, 123.2, 121.4, 116.4, 114.6, 68.4, 31.3, 19.3, 13.9; IR (KBr, cm^-1): 3056, 2961, 2934, 2870, 1672, 1605, 1566, 1511, 1482, 1437, 1414, 1294, 1224, 1111, 1074, 1043, 972, 953, 856, 841, 823, 810, 762; Anal. calcd for C₂₄H₂₁NO₂S: C 74.39, H 5.46, N 3.61; found: C 74.43, H 5.50, N 3.57.

(2-Benzo[d]thiazol-2-yl-5-tert-butyl-phenyl)-phenyl-methanone (5a):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 7.86 (d, 1H, J = 12.0 Hz), 7.78−7.74 (m, 3H), 7.63 (d, 1H, J = 8.4 Hz), 7.53 (s, 1H), 7.38−7.33 (m, 2H), 7.31−7.24 (m, 4H), 1.38 (s, 9H); ¹³C NMR (CDCl3, 100 MHz): δ 198.3, 165.5, 154.2, 153.7, 139.5, 138.1, 135.3, 132.7, 129.6, 129.4, 128.3, 127.4, 126.2, 125.9, 125.3, 123.4, 121.5, 35.3, 31.3; IR (KBr, cm^-1): 3069, 3028, 2967, 2930, 2867, 1671, 1596, 1558, 1515, 1481, 1449, 1431, 1395, 1362, 1314, 1253, 1162, 1103, 1023, 972, 902, 857, 840, 800, 757; Anal. calcd for C24H21NOS: C 77.59, H 5.70, N 3.77;

found: C 77.64, H 5.75, N 3.73

(2-Benzo[d]thiazol-2-yl-5-chloro-phenyl)-phenyl-methanone (6a):

White solid; M.p. 132 ^oC; ¹H NMR (CDCl3, 400 MHz): δ 7.87 (d, 1H, J = 8.4 Hz), 7.78−7.75 (m, 3H), 7.60 (d, 1H, J = 8.4 Hz), 7.51 (s, 1H), 7.43−7.38 (m, 2H), 7.36−7.26

153.5, 141.3, 137.4, 136.9, 135.4, 133.2, 130.9, 130.7, 130.4, 129.4, 129.0, 128.5, 126.5, 125.7, 123.6, 121.6; IR (KBr, cm^-1): 3063, 3022, 2923, 2848, 1670, 1593, 1581, 1560, 1508, 1474, 1452, 1432, 1378, 1313, 1291, 1263, 1181, 1156, 1128, 1100, 1021, 1001, 968, 947, 876, 817, 782, 755; Anal. calcd for C₂₀H₁₂ClNOS: C 68.67, H 3.46, N 4.00; found: C 68.71, H 3.52, N 3.93.

(2-(Benzo[d]thiazol-2-yl)-3-chlorophenyl)(phenyl)methanone (7a):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 8.12 (d, 1H, J = 7.2 Hz), 7.89 (d, 1H, J = 8.0 Hz), 7.80−7.75 (m, 1H), 7.70−7.58 (m, 3H), 7.54 (t, 1H, J = 7.6 Hz), 7.50−7.46 (m, 1H), 7.41−7.33 (m, 2H), 7.31−7.23 (m, 2H); ¹³C NMR (CDCl3, 100 MHz): δ 195.9, 168.4, 152.3, 143.1, 137.1, 133.9, 133.0, 131.9, 130.4, 129.8, 129.4, 129.1, 128.3, 127.6, 126.2, 125.8, 123.7, 121.4; IR (KBr, cm^-1): 3058, 3022, 2920, 2839, 2360, 2340, 1669, 1595, 1579, 1556, 1506, 1482, 1447, 1429, 1415, 1315, 1282, 1255, 1177, 1155, 1141, 1127, 1072, 1012, 968, 952, 924, 853, 798, 759; Anal. calcd for C20H12ClNOS: C 68.67, H 3.46, N 4.00; found: C 68.69, H 3.49, N 3.94.

(2-Benzo[d]thiazol-2-yl-4-fluoro-phenyl)-phenyl-methanone (8a):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 7.79 (t, 2H, J = 7.8 Hz), 7.74 (d, 2H, J = 7.2 Hz), 7.64 (d, 1H, J = 9.2 Hz), 7.57−7.54 (m, 1H), 7.40−7.34 (m, 2H), 7.33−7.26 (m, 4H); ¹³C NMR (CDCl₃, 100 MHz): δ 196.7, 164.6, 164.1, 153.5, 137.8, 135.9, 135.6, 133.0, 131.4, 131.3, 129.4, 128.5, 126.5, 125.8, 123.8, 121.6, 117.5, 117.2, 116.9, 116.7; IR (KBr, cm^-1): 3079, 3059, 3024, 1666, 1602, 1577, 1507, 1485, 1459, 1446, 1430, 1315, 1279, 1261, 1238, 1173, 1146, 1126, 1113, 1072, 998, 955, 927, 897,

873, 832, 821, 795, 761; Anal. calcd for C₂₀H₁₂FNOS: C 72.05, H 3.63, N 4.20; found: C 72.10, H 3.68, N 4.15.

(2-Benzo[d]thiazol-2-yl-4-bromo-phenyl)-phenyl-methanone (9a):

Gummy; ¹H NMR (CDCl₃, 400 MHz): δ 7.91 (s, 1H), 7.79 (d, 1H, J = 8.0 Hz), 7.75 (t, 2H, J = 9.0 Hz), 7.56 (d, 1H, J = 8.0 Hz), 7.47 (d, 1H, J = 8.0 Hz), 7.39−7.33 (m, 3H), 7.31−7.24 (m, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 196.7, 163.8, 153.4, 138.1, 137.6, 136.3, 135.5, 134.0, 133.1, 130.5, 130.4, 129.6, 129.4, 128.4, 126.5, 125.8, 123.7, 121.6; IR (KBr, cm^-1): 3070, 3053, 3022, 2925, 2841, 1665, 1596, 1681, 1551, 1500, 1473, 1445, 1434, 1381, 1316, 1276, 1251, 1239, 1151, 1096, 1012, 984, 934, 871, 827, 793, 763; HRMS (ESI) calcd for C20H12BrNOS (M + H⁺) 393.9896, found 393.9894.

(2-(Benzo[d]thiazol-2-yl)-5-methoxyphenyl)(p-tolyl)methanone (3d):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 7.98 (d, 2H, J = 8.0 Hz), 7.87 (d, 1H, J = 8.4 Hz), 7.74 (t, 1H, J = 6.8 Hz), 7.67 (d, 1H, J = 8.0 Hz), 7.32 (t, 1H, J = 7.8 Hz), 7.25 (d, 2H, J = 8.4 Hz), 7.11−7.07 (m, 2H), 6.97 (s, 1H), 3.87 (s, 3H), 2.41 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 197.2, 161.3, 153.7, 144.7, 143.9, 141.7, 135.2, 131.4, 130.5, 129.7, 129.4, 129.2, 126.2, 125.1, 123.3, 121.5, 115.9, 113.9, 55.9, 21.8; IR (KBr, cm^-1): 3055, 2960, 2917, 2832, 2538, 1670, 1604, 1569, 1482, 1409, 1317, 1293, 1267, 1227, 1179, 1112, 1040, 971, 884, 858, 842, 811, 756; HRMS (ESI) calcd for C22H17NO2S (M + H⁺) 360.1053, found 360.1052.

(2-(Benzo[d]thiazol-2-yl)-5-butoxyphenyl)(p-tolyl)methanone (4d):

White solid; M.p. 145−146 ^oC; ¹H NMR (CDCl₃, 400 MHz): δ 7.87 (d, 1H, J = 8.8 Hz), 7.75 (t, 2H, J = 7.0 Hz), 7.69 (d, 2H, J = 8.4 Hz), 7.33 (t, 1H, J = 7.2 Hz),

7.27−7.23 (m, 2H), 7.09 (d, 2H, J = 7.6 Hz), 6.97 (d, 1H, J = 2.4 Hz), 4.04 (t, 2H, J = 6.6 Hz), 2.29 (s, 3H), 1.81−1.77 (m, 2H), 1.55−1.47 (m, 2H), 0.98 (t, 3H, J = 7.4 Hz); ¹³C NMR (CDCl3, 100 MHz): δ 197.2, 165.4, 160.9, 153.7, 143.8, 141.6, 135.3, 135.2, 131.4, 130.4, 129.7, 129.2, 126.1, 125.0, 123.3, 121.4, 116.3, 114.4, 68.4, 31.3, 21.8, 19.3, 13.9; IR (KBr, cm^-1): 2963, 2939, 2919, 2869, 1672, 1603, 1567, 1482, 1438, 1412, 1313, 1292, 1264, 1223, 1184, 1110, 1044, 971, 909, 877, 858, 810, 762; Anal. calcd for C25H23NO2S: C 74.78, H 5.77, N 3.49; found: C 74.80, H 5.82, N 3.45.

(2-(Benzo[d]oxazol-2-yl)phenyl)(phenyl)methanone (1'a):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.13 (d, 2H, J = 8.4 Hz), 7.80 (d, 1H, J = 8.4 Hz), 7.68−7.59 (m, 4H), 7.50−7.44 (m, 4H), 7.36−7.32 (m, 1H), 7.25−7.23 (m, 1H); ¹³C NMR (CDCl₃, 100 MHz): δ 197.3, 161.0, 150.7, 141.5, 140.1, 137.4, 133.9, 133.2, 131.3, 130.3, 129.6, 129.5, 128.8, 128.6, 125.5, 124.8, 120.4, 110.6; IR (KBr, cm^-1): 3071, 3025, 2880, 2836, 2672, 2602, 2557, 2084, 1989, 1788, 1687, 1601, 1582, 1495, 1453, 1424, 1326, 1291, 1180, 1127, 1070, 1026, 999, 933, 809, 746; Anal.

calcd for C₂₀H₁₃NO₂: C 80.25, H 4.38, N 4.68; found: C 80.30, H 4.40, N 4.62.

(2-(Benzo[d]oxazol-2-yl)phenyl)(p-tolyl)methanone (1'd):

White solid; M.p. 126−127 ^oC; ¹H NMR (CDCl₃, 400 MHz): δ 8.24−8.21 (m, 1H), 7.63 (d, 1H, J = 8.0 Hz), 7.58−7.53 (m, 4H), 7.43−7.41 (m, 1H), 7.29−7.26 (m, 1H), 7.19−7.14 (m, 2H), 7.07 (d, 2H, J = 8.4 Hz), 2.25 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 196.9, 161.6, 150.8, 144.1, 141.8, 140.5, 134.9, 131.2, 130.1, 129.8, 129.4, 129.3, 128.6, 125.4, 124.6, 120.5, 110.7, 21.8; IR (KBr,

cm^-1): 3065, 3037, 2919, 2851, 1734, 1660, 1603, 1557, 1451, 1434, 1298, 1280, 1236, 1180, 1150, 1112, 1064, 1029, 930, 835, 810, 795, 770, 759, 741;HRMS (ESI) calcd for C21H15NO2 (M + H⁺) 314.1176, found 314.1177.

(2-(Benzo[d]oxazol-2-yl)phenyl)(4-biphenyl)methanone (1'e):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.34−8.32 (m, 1H), 8.13 (d, 2H, J = 7.6 Hz), 7.89−7.87 (m, 1H), 7.71−7.62 (m, 4H), 7.59−7.53 (m, 4H), 7.48 (t, 2H, J = 7.6 Hz), 7.44−7.40 (m, 1H), 7.38−7.34 (m, 1H), 7.26−7.23 (m, 1H); ¹³C NMR (CDCl3, 100 MHz): δ 190.9, 166.1, 150.8, 145.9, 141.7, 137.5, 133.9, 131.3, 130.4, 129.5, 129.1, 128.7, 128.4, 127.4, 127.3, 125.5, 124.8, 120.5, 110.7, 109.9; IR (KBr, cm^-1): 3069, 3030, 2953, 2924, 2849, 2670, 2555, 1688, 1601, 1582, 1559, 1452, 1423, 1325, 1291, 1179, 1126, 1071, 1026, 933, 854, 810, 760, 744; Anal. calcd for C26H17NO2: C 83.18, H 4.56, N 3.73; found: C 83.23, H 4.60, N 3.71.

(2-(Benzo[d]oxazol-2-yl)phenyl)(3-chlorophenyl)methanone (1'h):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.31 (d, 1H, J = 6.8 Hz), 7.82 (s, 1H), 7.70−7.64 (m, 3H), 7.63−7.60 (m, 1H), 7.52 (d, 1H, J = 6.8 Hz), 7.43−7.38 (m, 2H), 7.30−7.24 (m, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 196.0, 161.2, 150.7, 141.7, 139.5, 139.2, 134.9, 133.9, 133.2, 131.4, 130.7, 130.4, 130.0, 129.9, 129.4, 128.7, 127.8, 125.5, 124.9, 120.5, 110.7; IR (KBr, cm^-1): 3064, 2950, 2924, 2853, 1678, 1614, 1572, 1467, 1452, 1424, 1343, 1287, 1243, 1195, 1154, 1074, 1034, 1001, 943, 927, 892, 814, 761; Anal. calcd for C20H12ClNO2: C 71.97, H 3.62, N 4.20; found: C 72.01, H 3.66, N 4.16.

O N O

Ph

O N O

Cl

(2-(Benzo[d]oxazol-2-yl)-5-methylphenyl)(phenyl)methanone (2'a):

White solid; M.p. 120−121 ^oC; ¹H NMR (CDCl3, 400 MHz): δ 8.17 (d, 1H, J = 8.0 Hz), 7.78 (d, 2H, J = 8.0 Hz), 7.58−7.56 (m, 1H), 7.46−7.43 (m, 1H), 7.40 (d, 1H, J

= 7.2 Hz), 7.33−7.28 (m, 4H), 7.21−7.19 (m, 2H), 2.46 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 197.6, 161.7, 150.7, 142.1, 141.9, 140.2, 137.6, 133.2, 131.1, 129.6, 129.4, 129.3, 128.5, 125.2, 124.6, 122.8, 120.3, 110.6, 21.7; IR (KBr, cm^-1): 3067, 3034, 2921, 2852, 1773, 1672, 1613, 1593, 1555, 1494, 1451, 1396, 1343, 1314, 1291, 1264, 1241, 1213, 1178, 1127, 1047, 1002, 964, 926, 890, 843, 824, 812, 762; Anal. calcd for C21H15NO2: C 80.49, H 4.82, N 4.47; found: C 80.54, H 4.86, N 4.45.

(2-(Benzo[d]oxazol-2-yl)-5-methoxyphenyl)(phenyl)methanone (3'a):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.25 (d, 1H, J = 8.8 Hz), 7.82 (d, 1H, J = 8.0 Hz), 7.58−7.56 (m, 1H), 7.49−7.43 (m, 2H), 7.36−7.29 (m, 3H), 7.22−7.15 (m, 3H), 7.01 (s, 1H), 3.91 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 196.6, 162.3, 161.9, 150.7, 142.0, 137.4, 133.3, 131.2, 130.4, 129.6, 128.7, 128.6, 124.9, 124.5, 120.1, 116.1, 113.8, 110.5, 55.9; IR (KBr, cm^-1): 3061, 3003, 2964, 2931, 2837, 1737, 1672, 1617, 1598, 1577, 1557, 1493, 1452, 1414, 1315, 1296, 1270, 1243, 1230, 1177, 1123, 1103, 1061, 1028, 1001, 963, 925, 893, 843, 815, 790, 762; Anal. calcd for C21H15NO3: C 76.58, H 4.59, N 4.25; found: C 76.65, H 4.64, N 4.20.

(2-(Benzo[d]oxazol-2-yl)-5-chlorophenyl)(phenyl)methanone (6'a):

Gummy; ¹H NMR (CDCl3, 400 MHz): δ 8.68 (s, 1H), 8.25 (d, 1H, J = 8.8 Hz), 8.12 (d, 1H, J = 7.6 Hz), 7.86−7.83 (m, 1H), 7.80 (d, 1H, J = 7.8 Hz), 7.65−7.59 (m, 2H), 7.50−7.45 (m, 2H), 7.39−7.33 (m, 2H),

7.27−7.23 (m, 1H); ¹³C NMR (CDCl3, 100 MHz): δ 195.7, 162.4, 150.7, 141.6, 137.8, 136.9, 133.9, 133.6, 131.4, 130.7, 130.5, 130.4, 129.7, 128.9, 128.7, 128.6, 125.7, 124.9, 120.5, 110.7; IR (KBr, cm^-1): 3072, 2925, 2842, 2442, 1735, 1675, 1612, 1593, 1557, 1477, 1450, 1384, 1343, 1313, 1280, 1240, 1183, 1154, 1096, 1046, 951, 929, 881, 828, 807, 778, 761; Anal. calcd for C₂₀H₁₂ClNO₂: C 71.97, H 3.62, N 4.20; found: C 71.98, H 3.69, N 4.18.

(2-(5-Methylbenzo[d]oxazol-2-yl)phenyl)(phenyl)methanone (10'a):

White solid; M.p. 108.5 ^oC; ¹H NMR (CDCl3, 400 MHz):

δ 8.13 (d, 2H, J = 7.8 Hz), 7.79 (d, 1H, J = 7.8 Hz), 7.67−7.60 (m, 3H), 7.54−7.43 (m, 4H), 7.34 (t, 1H, J = 7.6 Hz), 7.21 (d, 1H, J = 8.4 Hz), 2.39 (s, 3H); ¹³C NMR (CDCl3, 100 MHz): δ 197.4, 161.6, 148.9, 141.8, 140.1, 137.5, 133.9, 133.2, 131.2, 130.4, 129.6, 129.4, 128.8, 128.7, 128.5, 126.6, 120.3, 110.0, 21.6; IR (KBr, cm^-1):

3071, 3011, 2961, 2889, 2850, 2677, 2559, 1787, 1687, 1601, 1582, 1453, 1424, 1326, 1291, 1180, 1127, 1072, 1026, 933, 802, 707; HRMS (ESI) calcd for C21H15NO2

(M + H⁺) 314.1176, found 314.1176.