Journal of the Iranian Chemical Society
1H, S-CHa), 4.68 (d, JHb,Ha = 12.6 Hz, 1H, S-CHb), 3,75
(s, 3H, OCH3); 13C-NMR (125 MHz, DMSO-d6): δC 193.5,
159.9, 157.2, 155.0, 149.9, 146.9, 141.2, 135.0, 131.9,
130.5, 129.6, 129.6, 126.6, 126.1, 126.1, 125.5, 123.9,
123.9, 120.9, 119.1, 112.8, 55.9, 39.1; EI-MS: m/z (rel.
abundance%) = 447 [M]+ (15), 415 (28), 384 (100), 297
(91), 234 (63), 150 (48); HREI-MS Calcd for C23H17N3O5S:
m/z=447.0889, found: 447.0868.
HREI-MS Calcd for C23H14ClF3N2O2S: m/z = 494.9888,
found: 494.9879.
3‑(2,3‑Dichlorophenyl)‑2‑((2‑(4‑nitrophenyl)‑2‑oxoethyl)
thio) quinazolin‑4(3H)‑one (14)
White solid; Yield: 53%; M.P.: 211–214 °C; Rf = 0.29
(100% DCM); 1H-NMR (300 MHz, DMSO-d6): δH
8.39 (d, J3′′,2′′ = J5′′,6′′ = 8.8 Hz, 2H, H-3′′, H-5′′), 8.29
(d, J2′′,3′′ = J6′′,5′′ = 8.8 Hz, 2H, H-2′′, H-6′′), 8.04 (d,
J5,6 = 7.6 Hz, 1H, H-5), 7.92 (d, J4′,5′ = 8.0 Hz, 1H, H-4′),
7.75 (ovp, 2H, H-6, H-6′), 7.64 (t, J7(6,8) =8.4 Hz, 1H, H-7),
7.45 (t, J5′(4′,6′) = 7.6 Hz, 1H, H-5′), 7.08 (d, J8,7 = 8.4 Hz.
1H, H-8), 4.84 (d, JHa,Hb = 16.8 Hz, 1H, S-CHa), 4.77 (d,
JHb,Ha =16.8 Hz, 1H, S-CHb); 13C-NMR (125 MHz, DMSO-
d6): δC 193.0, 159.6, 155.5, 150.0, 146.8, 141.1, 137.2,
135.5, 132.8, 132.6, 131.2, 130.6, 129.7, 129.7, 129.3,
126.7, 126.5, 125.7, 123.9. 123.9, 118.9, 39.2; EI-MS: m/z
(rel. abundance%) = 485 [M]+ (9), 487 [M + 2] (6), 489
[M + 4] (2), 450 (100), 452 (41) 418 (13), 335 (36), 287
(35), 150 (37); HREI-MS Calcd for C23H14ClF3N2O2S:
m/z=485.0004, found: 484.9983.
3‑(4‑Methoxyphenyl)‑2‑((2‑(4‑nitrophenyl)‑2‑oxoethyl)
thio) quinazolin‑4(3H)‑one (11) CAS#760195‑87‑7
Of white solid; Yield: 70%; M.P.: 209–212 °C; Rf = 0.43
(100% DCM); 1H-NMR (400 MHz, DMSO-d6): δH
8.42 (d, J3′′,2′′ = J5′′,6′′ = 6.3 Hz, 2H, H-3′′, H-5′′), 8.31 (d,
J2′′,3′′ =J6′′,5′′ =6.0 Hz, 2H, H-2′′, H-6′′), 8.03 (d, J5,6 =5.7 Hz,
1H, H-5), 7.70 (t, J7(6,8) =5.7 Hz, 1H, H-7), 7.42 (ovp, 3H,
H-2′, H-6′), 7.14 (d, J3′,2′ = J5′,6′ = 6.3 Hz, 2H, H-3′, H-5′),
7.03 (d, J8,7 =6.0 Hz, 1H, H-8), 4.72 (s, 1H, S-CH2), 3.85 (s,
3H, OCH3); EI-MS: m/z (rel. abundance%)=447 [M]+ (30),
415 (83), 297 (92), 285 (68), 265 (100), 251 (60), 150 (45).
3‑(4‑Ethoxyphenyl)‑2‑((2‑(4‑nitrophenyl)‑2‑oxoethyl) thio)
quinazolin‑4(3H)‑one (12) CAS#768287‑72‑5
3‑(2‑Chlorophenyl)‑2‑((2‑(4‑nitrophenyl)‑2‑oxoethyl) thio)
quinazolin‑4(3H)‑one (15)
Of white solid; Yield: 70%; M.P.: 246–249 °C; Rf = 0.45
(100% Dichloromethane); 1H-NMR (400 MHz, DMSO-d6):
δH 8.42 (d, J3′′,2′′ =J5′′,6′′ =6.6 Hz, 2H, H-3′′, H-5′′), 8.31 (d,
J2′′,3′′ =J6′′,5′′ =6.6 Hz, 2H, H-2′′, H-6′′), 8.03 (d, J5,6 =6.0 Hz,
1H, H-5), 7.70 (t, J7(6,8) = 5.7 Hz, 1H, H-7), 7.42 (t,
J6(5,7) =6.0 Hz, 1H, H-6), 7.37 (d, J2′,3′ =J6′,5′ =6.6 Hz, 2H,
H-2′, H-6′), 7.11 (d, J3′,2′ = J5′,6′ = 6.3 Hz, 2H, H-3′, H-5′),
7.02 (d, J8,7 =6.3 Hz, 1H, H-8), 4.72 (s, 2H, S-CH2), 4.15
(q, JCH2,CH3 =6.8 Hz, 2H, OCH2), 1.39 (t, JCH3,CH2 =5.4 Hz,
3H, CH3); EI-MS: m/z (rel. abundance%)=461 [M]+ (33),
429 (93), 400 (27), 298 (64), 279 (84).
Yellow solid; Yield: 70%; M.P.: 187–189 °C; Rf = 0.31
(100% DCM); 1H-NMR (400 MHz, DMSO-d6): δH
8.41 (d, J3′′,2′′ = J5′′,6′′ = 9.2 Hz, 2H, H-3′′, H-5′′), 8.32 (d,
J2′′,3′′ =J6′′,5′′ =8.8 Hz, 2H, H-2′′, H-6′′), 8.06 (d, J5,6 =8 Hz,
J5,7 = 1.2 Hz, 1H, H-5), 7.79 (ovp, 5H, H-7, H-3′, H-4′,
H-5′, H-6′), 7.46 (t, J6(5,7) = 7.2 Hz, 1H, H-6), 7.10 (d,
J8,7 = 8.0 Hz, 1H, H-8), 4.85 (d, JHa,Hb = 16.8 Hz, 1H,
S-CHa), 4.76 (d, JHb,Ha =16.8 Hz, 1H, S-CHb); 13C-NMR
(125 MHz, DMSO-d6): δC 193.2, 159.7, 155.9, 149.9, 146.8,
141.1, 135.3, 133.1, 132.4, 132.2, 131.6, 130.3, 129.7,
129.7, 128.7, 126.7, 126.3, 125.6, 123.9, 123.9, 118.9, 39.2;
EI-MS: m/z (rel. abundance%)=451 [M]+ (10), 453 [M+2]
(4), 416 (100), 384 (46), 301 (37), 253 (14), 234 (35), 150
(31); HREI-MS Calcd for C22H14ClN3O4S: m/z=451.0394,
found: 451.0384.
3‑(3‑Bromophenyl)‑2‑((2‑(4‑nitrophenyl)‑2‑oxoethyl) thio)
quinazolin‑4(3H)‑one (13)
White solid; Yield: 75%; M.P.: 226–228 °C; Rf = 0.34
(100% DCM); 1H-NMR (400 MHz, DMSO-d6): δH
8.42 (d, J3′′,2′′ = J5′′,6′′ = 6.9 Hz, 2H, H-3′′, H-5′′), 8.31
(d, J2′′,3′′ = J6′′,5′′ = 6.6 Hz. 2H, H-2′′, H-6′′), 8.04 (dd,
J5,6 = 5.7 Hz, J5,7 = 1.0 Hz, 1H, H-5), 7.85 (ovp, 2H, H-8,
H-6′), 7.72 (dt, J7(6,8) =6.3 Hz, J7,5 =1.2 Hz, 1H, H-7), 7.60
(ovp, 2H, H-4′, H-5′), 7.44 (t, J6,7 =6.3 Hz, 1H, H-6), 7.04
(d, J6′,5′ =6.0 Hz, 1H, H-6′), 4.76 (s, 2H, S-CH2); 13C-NMR
(125 MHz, DMSO-d6): δC 193.3, 160.4, 156.0, 150.0, 146.8,
141.2, 137.3, 135.0, 133.1, 132.3, 131.4, 129.6, 129.6,
128.8, 126.6, 126.1, 125.5, 123.9, 123.9, 121.7, 119.4, 39.9;
EI-MS: m/z (rel. abundance%)=495 [M]+ (30), 497 [M+2]
(32), 464 (36), 347 (100), 333 (61), 234 (65), 150 (53);
2‑((2‑(4‑Nitrophenyl)‑2‑oxoethyl)
thio)‑3‑(3‑(trifuoromethyl) phenyl) quinazolin‑4(3H)‑one
(16)
Of white solid; Yield: 70%; M.P.: 210–212 °C; Rf = 0.42
(100% DCM); 1H-NMR (400 MHz, DMSO-d6): δH
8.42 (d, J3′′,2′′ = J5′′,6′′ = 8.8 Hz, 2H, H-3′′, H-5′′), 8.31
(d, J2′′,3′′ = J6′′,5′′ = 8.8 Hz, 2H, H-2′′, H-6′′), 8.04 (ovp,
3H, H-5, H-2′, H-4′), 7.87 (ovp, 2H, H-5′, H-6′), 7.73
(dt, J7(6,8) = 8.4 Hz, J7,5 = 1.2 Hz, 1H, H-7), 7.45 (dt,
J6(5,7) =8.0 Hz, J6,8 =0.8 Hz, 1H, H-6), 7.06 (d, J8,7 =8.0 Hz,
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