338
S. Maddila, G. L. V. Damu, E. O. Oseghe, O. A. Abafe, C. Venakata Rao, and P. Lavanya
-1
1708 (C=O), 1613 (C=N), 1528 (C=C), 754 (C-Br) cm ;
-1 1
1718 (C=O), 1610 (C=N), 1538 (C=C) cm ; H NMR
(300 MHz, DMSO-d6) δ 1.10 (t, 6H, OCH2CH3), 2.39 (s, 3H,
ArCH3), 2.84 (s, 6H, -N(CH3)2), 4.10 (q, 4H, OCH2CH3),
6.24 (s, 1H, -CH), 6.65-8.65 (m, 13H, =CH & Ar-H); LCMS:
(m/z) 596 [M+H]. Anal. Calcd. for C34H33N3O5S: C,
68.55; H, 5.58; N, 7.05. Found: C, 68.61; H, 5.60; N, 6.98.
Ethyl 2-(4-chlorobenzylidene)-5-(3'-(ethoxycarbonyl)
biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thia-
zolo[3,2-a]pyrimidine-6-carboxylate (8g)
1
H NMR (300 MHz, DMSO-d6) δ 1.20 (t, 6H, OCH2CH3),
2.39 (s, 3H, ArCH3), 4.10 (q, 4H, OCH2CH3), 6.23 (s, 1H,
-CH), 7.10-8.60 (m, 13H, =CH & Ar-H); LCMS: (m/z)
632 [M+2H]. Anal. Calcd. for C32H27BrN2O5S: C, 80.85;
H, 4.32; N, 4.44. Found: C, 80.76; H, 4.37; N, 4.39.
Ethyl 2-(4-ethylbenzylidene)-5-(3'-(ethoxycarbonyl)
biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thia-
zolo[3,2-a]pyrimidine-6-carboxylate (8c)
o
Yield: 56%; mp 198-200 C; IR (KBr) υ 2969 (C-H),
o
Yield: 77%; mp 244-246 C; IR (KBr) υ 2981 (C-H),
-1
1
-1
1721 (C=O), 1628 (C=N), 1552 (C=C), 823 (C-Cl) cm ;
1711 (C=O), 1609 (C=N), 1546 (C=C) cm ; H NMR (300
MHz, DMSO-d6) δ 1.15 (t, 9H, OCH2CH3 & -ArCH2CH3 ),
2.34 (s, 3H, ArCH3), 2.40 (q, 2H, -ArCH2CH3), 4.10 (q,
4H, OCH2CH3), 6.20 (s, 1H, -CH), 6.75-8.55 (m, 13H,
=CH & Ar-H); LCMS: (m/z) 581 [M+H]. Anal. Calcd. for
C34H32N2O5S: C, 70.32; H, 5.55; N, 4.82. Found: C, 70.36;
H, 5.48; N, 4.85.
1
H NMR (300 MHz, DMSO-d6) δ 1.15 (t, 6H, OCH2CH3),
2.38 (s, 3H, ArCH3), 4.15 (q, 4H, OCH2CH3), 6.24 (s, 1H,
-CH), 7.10-8.60 (m, 13H, =CH & Ar-H); LCMS: (m/z) 587
[M+H]. Anal. Calcd. for C32H27ClN2O5S: C, 65.48; H, 4.65;
N, 4.78. Found: C, 65.55; H, 4.59; N, 4.82.
Ethyl 2-(4-isopropylbenzylidene)-5-(3'-(ethoxycarbo-
nyl)biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-2H-
thiazolo[3,2-a]pyrimidine-6-carboxylate (8h)
Ethyl 2-(4-methylbenzylidene)-5-(3'-(ethoxycarbonyl)
biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thia-
zolo[3,2-a]pyrimidine-6-carboxylate (8d)
o
Yield: 88%; mp 187-189 C; IR (KBr) υ 2972 (C-H), 1714
o
Yield: 87%; mp 235 C; IR (KBr) υ 2976 (C-H), 1710
-1 1
(C=O), 1618 (C=N), 1528 (C=C), cm ; H NMR (300 MHz,
DMSO-d6) δ 0.95-1.35 (m, 12H, OCH2CH3), 2.33 (s, 3H,
ArCH3), 2.60 (m, 1H, -ArCH(CH3)2), 4.10 (q, 4H, OCH2CH3),
6.20 (s, 1H, -CH), 7.15-8.65 (m, 13H, =CH & Ar-H);
LCMS: (m/z) 595 [M+H]. Anal. Calcd. for C35H34N2O5S:
C, 70.68; H, 5.76; N, 4.73. Found: C, 70.73; H, 5.68; N, 4.69.
Ethyl 2-(4-tert-butylbenzylidene)-5-(3'-(ethoxycarbo-
nyl)biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-2H-
thiazolo[3,2-a]pyrimidine-6-carboxylate (8i)
-1
1
(C=O), 1617 (C=N), 1544 (C=C) cm ; H NMR (300 MHz,
DMSO-d6) δ 1.15 (t, 6H, OCH2CH3), 2.30 (s, 6H, ArCH3),
4.10 (q, 4H, OCH2CH3), 6.18 (s, 1H, -CH), 6.90-8.55 (m,
13
13H, =CH & Ar-H); C NMR (DMSO-d6, δ, ppm) 13.7,
13.9, 19.9, 24.3, 55.1, 61.8, 63.2, 113.2, 121.3, 124.8, 125.6,
126.2, 126.4, 127.1, 127.7, 128.3, 129.1, 130.6, 131.3,
136.8, 137.2, 139.5, 141.6, 141.8, 154.9, 162.3, 166.5,
167.4, 171.2; LCMS: (m/z) 567 [M+H]. Anal. Calcd. for
C33H30N2O5S: C, 69.94; H, 5.34; N, 4.94. Found: C, 70.01;
H, 5.39; N, 4.87.
o
Yield: 74%; mp 211-212 C; IR (KBr) υ 2974 (C-H),
-1
1
1713 (C=O), 1616 (C=N), 1538 (C=C) cm ; H NMR
(300 MHz, DMSO-d6) δ 1.10-1.48 (m, 15H, OCH2CH3 &
-ArC(CH3)3), 2.35 (s, 3H, ArCH3), 4.10 (q, 4H, OCH2CH3),
6.22 (s, 1H, -CH), 7.10-8.55 (m, 13H, =CH & Ar-H); LCMS:
(m/z) 609 [M+H]. Anal. Calcd. for C36H36N2O5S: C,
71.04; H, 5.97; N, 4.60. Found: C, 70.97; H, 6.02; N, 4.57.
Ethyl 2-(4-nitrobenzylidene)-5-(3'-(ethoxycarbonyl)
biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo
[3,2-a]pyrimidine-6-carboxylate (8j)
Ethyl 2-(4-methoxybenzylidene)-5-(3'-(ethoxycarbo-
nyl)biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-2H-
thiazolo[3,2-a]pyrimidine-6-carboxylate (8e)
o
Yield: 82%; mp 265-266 C; IR (KBr) υ 2980 (C-H),
-1
1
1706 (C=O), 1606 (C=N), 1568 (C=C) cm ; H NMR
(300 MHz, DMSO-d6) δ 1.10 (t, 6H, OCH2CH3), 2.38 (s,
3H, ArCH3), 3.78 (s, 3H, OCH3), 4.15 (q, 4H, OCH2CH3),
13
6.28 (s, 1H, -CH), 6.60-8.75 (m, 13H, =CH & Ar-H); C
o
Yield: 69%; mp 219-220 C; IR (KBr) υ 2980 (C-H),
NMR (DMSO-d6, δ, ppm) 13.8, 14.2, 21.2, 54.8, 55.3,
62.7, 63.5, 115.2, 123.1, 124.4, 125.8, 126.0, 126.3, 127.8,
128.6, 129.6, 130.0, 131.1, 131.8, 137.9, 141.0, 141.9,
142.6, 154.6, 160.2, 162.6, 166.5, 167.6, 171.3; LCMS:
(m/z) 583 [M+H]. Anal. Calcd. for C33H30N2O6S: C, 68.02;
H, 5.19; N, 4.82. Found: C, 67.95; H, 5.24; N, 4.79.
Ethyl 2-(4-(dimethylamino)benzylidene)-5-(3'-(etho-
xycarbonyl)biphenyl-4-yl)-7-methyl-3-oxo-3,5-dihydro-
2H-thiazolo[3,2-a]pyrimidine-6-carboxylate (8f)
-1
1
1720 (C=O), 1632 (C=N), 1555 (C=C) cm ; H NMR
(300 MHz, DMSO-d6) δ 1.18 (t, 6H, OCH2CH3), 2.39 (s,
3H, ArCH3), 4.10 (q, 4H, OCH2CH3), 6.28 (s, 1H, -CH),
13
7.10-8.65 (m, 13H, CH & Ar-H); C NMR (DMSO-d6, δ,
ppm) 13.6, 14.1, 21.3, 54.8, 63.1, 63.9, 115.2, 121.4, 123.8, 124.8,
125.4, 126.1, 127.4, 128.3, 128.9, 130.9, 131.7, 138.2, 140.8,
141.2, 141.9, 142.0, 148.5, 154.7, 162.4, 166.6, 167.7, 171.4;
LCMS: (m/z) 598 [M+H]. Anal. Calcd. for C32H27N3O7S: C,
64.31; H, 4.55; N, 7.02. Found: C, 64.42; H, 4.61; N, 6.95.
o
Yield: 92%; mp 210-212 C; IR (KBr) υ 2973 (C-H),
Journal of the Korean Chemical Society