Table 2 Spectral data of the synthesized compounds and intermediate (Int.)

Int.

–

817 (N–H str., NH₂), 1265 (C–N str., Ar–NH₂)

7.19–7.56 (m, 4H, ArH), 6.90 (s, 1H, CH of thiazole), 4.12 (s, 2H, –NH₂ of thiazole)

127.4, 131.1, 122.6, 130.2, 127.3, 130.8 (6C, phenyl nucleus), 167.7, 100.4, 151.5 (3C, thiazole)

Theoretical calc: C, 42.37; H, 2.77; N, 10.98; Found: C, 42.31; H, 2.74; N, 10.89

p1

1266

–

6.93 (m, 7H, aromatic H), 7.42 (s, 1H, CH of thiazole)

120.4, 109.4, 128.7, 122.2, 110.3, 150.87, 123.2, 110.0, 150.2, 110.6, 148.5, 128.6 (12C, phenyl nucleus), 150.3, 172.41, 109.6 (3C, thiazole), 159.4 (N=CH), 55.2, 54.6 (2C, OCH₃)

Theoretical calc: C, 53.61; H, 3.75; N, 6.95; Found: C, 53.48; H, 3.69; N, 6.81

p2

1208

–

6.76–7.45 (m, 7H, ArH), 7.43 (s, 1H, C–H of thiazole), 8.85 (s, 1H, N=CH), 3.71 (s, 3H, OCH₃), 5.39 (s, 1H, OH)

130.4, 127.4, 124.7, 132.1, 130.3, 131.8, 119.8, 115.4, 150.2, 147.6, 113.4, 127.9, (12C, phenyl nucleus), 151.3, 173.1, 108.6 (3C, thiazole), 158.2 (N=CH), 55.7 (O–CH₃), 53.4 (1C, –OCH₃)

Theoretical calc: C, 52.45; H, 3.37; N, 7.20; Found: C, 52.33; H, 3.41; N, 7.18

p3

1229

830 [(C–N str., N(CH₃)₂]

6.80–7.41 (m, 8H, ArH), 7.80 (s, 1H, –N=CH), 3.43 (s, 3H, OCH₃), 7.45 (s, 1H, CH of thiazole)

130.4, 127.4, 124.7, 132.1, 130.3, 131.8, 124.6, 129.1, 110.8, 152.2, 110.8, 127.3 (12C, phenyl nucleus), 151.3, 173.41, 108.6 (3C, thiazole), 158.2 (N=CH), 40.8, 39.9 (2C, N(CH₃)₂)

Theoretical calc: C, 57.00; H, 4.53; N, 10.50; Found: C, 57.04; H, 4.42; N, 10.47

p4

1232

1325 (C–O str. and O–H in plane bending, phenol)

6.9–7.39 (m, 6H, ArH), 7.73 (s, 1H, –N=CH), 3.73 (s, 3H, OCH₃), 7.47 (s, 1H, CH of thiazole), 2.91 (s, 6H, N(CH₃)₂)

121.5, 107.2, 128.7, 123.1, 111.1, 151.2, 151.1, 102.3, 130.1, 103.1, 152.1, 140.5 (12C, phenyl nucleus), 149.3, 171.2, 109.8 (3C, thiazole), 160.1 (N=CH), 59.6, 55.8 (2C, OCH₃, 54.3, 58.5 (2C, OCH₃)

Theoretical calc: C, 52.66; H, 3.95; N, 6.46; Found: C, 52.54; H, 3.87; N, 6.44

p5

–

–

7.28–7.60 (m, 8H, ArH), 7.90 (s, 1H, N=CH), 7.49 (s, 1H, CH of thiazole)

120.1, 126.7, 123.1, 111.1, 151.2, 109.2, 130.1, 126.2, 131.2, 122.8, 129.7, 128.6, 131.2 (12C, phenyl nucleus), 149.3, 171.2, 109.8 (3C, thiazole), 160.1 (N=CH), 59.6 (C, –OCH₃)

Theoretical calc: C, 45.52; H, 2.39; N, 6.64; Found: C, 45.48; H, 2.27; N, 6.51

p6

–

1395 (C–O str. and O–H in plane bending, phenol),

7.36–8.01 (m, 10H, ArH), 8.14 (s, 1H, N=CH), 7.43 (s, 1H, CH of thiazole)

122.6, 126.7, 132.1, 118.1, 151.2, 128.21, 131.4, 119.5, 170.5, 107.9 (12C, naphthalene nucleus), 148.3, 169.1, 109.1 (3C, thiazole), 159.10 (N=CH)

Theoretical calc: C, 58.69; H, 3.20; N, 6.84; Found: C, 58.55; H, 3.18; N, 6.83

p7

–

725 (C–Cl str., ArCl)

7.24–7.58 (m, 8H, ArH), 7.90 (s, 1H, N=CH), 7.43 (s, 1H, CH of thiazole)

127.2, 129.4, 134.5, 129.8, 135.6, 126.3, 129.8, 133.2, 131.4, 124.8, 135.5 (12C, phenyl nucleus), 149.5, 173.2, 108.8 (3C, thiazole), 159.1 (N=CH)

Theoretical calc: C, 50.88; H, 2.67; N, 7.4; Found: C, 50.76; H, 2.51; N, 7.2

p8

1263

–

6.80–7.35 (m, 7H, ArH), 7.90 (s, 1H, N=CH), 7.36 (s, 1H, CH of thiazole), 3.88 (s, 1H, OCH₃)

124.2, 134.5, 130.2, 133.5, 128.8, 104.5, 132.1, 115.1, 158.3, 100.2, 161.8 (12 C, phenyl nucleus), 149.5, 173.2, 108.8 (3C, thiazole), 161.2 (N=CH), 54.6, 53.5 (2C, OCH₃)

Theoretical calc: C, 53.61; H, 3.75; N, 6.95; Found: C, 53.59; H, 3.64; N, 6.81

P9

1265

–

6.90–7.27 (m, 8H, ArH), 7.40 (s, 1H, N=CH), 7.38 (s, 1H, CH of thiazole), 3.90 (s, 1H, OCH₃)

125.2, 133.5, 131.2, 127.5, 126.8, 127.6, 120.1, 136.5, 110.1, 159.7 (12C, phenyl nucleus), 151.5, 172.3, 107.6 (3C, thiazole), 160.2 (N = CH), 54.3 (O-CH₃)

Theoretical calc: C, 54.70, H, 3.51; N, 7.50; Found: C, 54.56; H, 3.28; N, 7.38

p10

1265

1397 (C–O str. and O–H in plane bending, phenol)

6.70–7.38 (m, 8H, ArH), 9.70 (s, 1H, N=CH), 7.52 (s, 1H, CH of thiazole)

127.2, 132.5, 130.2, 126.5, 125.8, 115.2, 157.3, 112.2, 136.5, 120.0, 131.1 (12C, phenyl nucleus), 150.5, 171.3, 108.5 (3C, thiazole), 160.1 (N=CH)

Theoretical calc: C, 53.49; H, 3.09; N, 7.80; Found: C, 53.41; H, 3.07; N, 7.72