ACCEPTED MANUSCRIPT
125 MHz, δ, ppm): C 51.9(A), 52.0(B), 75.2, 86.0, 122.5, 125.0, 129.3, 129.7, 130.6, 131.6,
132.1, 132.9, 136.6, 141.2, 142.5, 142.8, 153.2, 157.3(B), 157.4(A), 159.11, 168.3. MS for
+
C19H13N3O3 : calcd. [M]+ 313.3, found 313.2. Elemental Analysis: calcd. C, 68.88; H, 3.95;
N, 12.68, found C, 68.88; H, 3.96; N, 12.69.
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3bc: White powder. m.p. 250-253 C. IR (KBr, cm-1) ν 1402, 1609, 1732 cm-1.1H NMR
(DMSO-d6, 300 MHz, δ, ppm): H 3.16 (3H, s, CH3), 5.43 (1H, s, COCH), 7.44-7.45 (1H, m,
Ar), 7.67-7.70 (2H, m, Ar), 7.88 (1H, s, OCHN), 8.05-8.07 (1H, m, Ar), 8.37-8.39 (2H, m,
+
Ar). MS for C19H11Cl2N3O3 : calcd. [M-CO2CH3]+ 340.0, found 340.1.Elemental Analysis:
calcd. C, 57.02; H, 2.77; N, 10.50, found C, 57.02; H, 2.78; N, 10.50.
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3ad: White powder. m.p. 184-186 C. IR (KBr, cm-1) ν 1161, 1402, 1604 cm-1. Two
diastereomer; major diast. (A) and minor diast. (B), 1H NMR (DMSO-d6, 300 MHz, δ, ppm):
H 2.42 (3H, s, CH3), 5.67(B) and 5.77(A) (1H, 2s, SO2CH), 6.89-7.05 (2H, m, Ar), 7.37-7.44
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(3H, m, Ar), 7.60-7.95 (4H, m, Ar and OCHN), 10.77(A) and 10.99(B) (1H, 2s, NH), C
NMR (DMSO-d6, 125 MHz, δ, ppm): C 13.6, 86.0, 101.9, 123.0, 130.4, 130.7, 132.4, 133.7,
134.4, 136.4, 140.5, 142.1, 143.0, 157.5, 167.7. MS for C17H14N2O4S+: calcd. [M]+ 342.4,
found 342.5. Elemental Analysis: calcd. C, 59.64; H, 4.12; N, 8.18; S, 9.36, found C, 59.64;
H, 4.14; N, 8.19; S, 9.36.
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3ae: White powder. m.p. 180-181 C. IR (KBr, cm-1) ν 1152, 1400, 1609 cm-1.1H NMR
(DMSO-d6, 300 MHz, δ, ppm): H 2.23 (3H, s, CH3), 2.41(3H, s, CH3), 5.73 (1H, s, SO2CH),
6.78 (1H, s, Ar), 7.18-7.43 (4H, m, Ar and OCHN), 7.874-7.89 (3H, m, Ar), 10.71 (1H, s,
NH), 13C NMR (DMSO-d6, 125 MHz, δ, ppm): C 21.2, 21.4, 81.8, 109.4, 110.1, 124.9,
126.0, 128.5, 129.9, 138.2, 140.9, 144.6, 146.0, 163.4, 178.4.MS for C18H16N2O4S+: calcd.
[M]+ 356.1, found 356.1. Elemental Analysis: calcd. C, 60.66; H, 4.53; N, 7.86; S, 9.00,
found C, 60.66; H, 4.55; N, 7.87; S, 9.00.
3af: Pale yellow powder. m.p. 191-192 oC. IR (KBr, cm-1) ν 1150, 1405, 1610 cm-1.1H NMR
(DMSO-d6, 300 MHz, δ, ppm): H 2.37 (3H, s, CH3), 5.89 (1H, s, SO2CH), 6.82 (1H, s, Ar),
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7.22-7.82 (7H, m, Ar and OCHN), 10.91 (1H, s, NH), C NMR (DMSO-d6, 125 MHz, δ,
ppm): C 21.6, 83.4, 112.7, 114.4, 128.7, 129.1, 129.5, 129.9, 134.8, 135.9, 142.4, 148.5,
159.1, 170.9. MS for C17H13N3O6S+: calcd. [M]+ 387.1, found 387.2. Elemental Analysis:
calcd. C, 52.71; H, 3.38; N, 10.85; S, 8.28, found C, 52.71; H, 3.39; N, 10.86; S, 8.28.
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3ag: Colorless crystal. m.p. 172-176 C. IR (KBr, cm-1) ν 1170, 1405, 1601 cm-1.1H NMR
(DMSO-d6, 300 MHz, δ, ppm): H 2.4 (3H, s, CH3), 4.92 (2H, s, CH2), 5.86 (1H, s, SO2CH),
6.97-7.00 (1H, m, Ar), 7.10-7.15 (1H, m, Ar), 7.28-7.42 (8H, m, Ar and OCHN), 7.66-7.73
(3H, m, Ar), 8.03 (1H, s, Ar). MS for C24H20N2O4S+: calcd. [M]+ 432.1, found 431.6.
Elemental Analysis: calcd. C, 66.65; H, 4.66; N, 6.48; S, 7.41, found C, 66.65; H, 4.68; N,
6.48; S, 7.40.
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3ah: Colorless crystal. m.p. 201-204 C.IR (KBr, cm-1) ν 1172, 1405, 1600 cm-1. H NMR
(DMSO-d6, 300 MHz, δ, ppm): H 2.43 (3H, s, CH3), 3.13 (3H, s, NCH3), 5.83 (1H, s,
SO2CH), 7.05-7.11 (1H, m, Ar), 7.40-7.44 (2H, m, Ar), 7.85-7.98 (4H, m, Ar and OCHN),
8.00 (1H, s, Ar), 13C NMR (DMSO-d6, 125 MHz, δ, ppm): C 21.6, 26.8, 73.1, 111.21, 126.0,
128.5, 130.2, 133.2, 134.8, 144.0, 145.4, 162.0, 174.4. MS for C18H15BrN2O4S+: calcd. [M]+
434.0, found 434.1. Elemental Analysis: calcd. C, 49.67; H, 3.47; N, 6.44; S, 7.37, found C,
49.67; H, 3.48; N, 6.46; S, 7.37.
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