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Organic & Biomolecular Chemistry
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ARTICLE
3-(((2-Chlorophenyl)(methyl)(oxo)-λ6-
sulfaneylidene)amino)quinoxalin-2(1H)-one (3g). Off-white solid
(260 mg, 78% yield); m.p. = 216.7−217.1 °C; 1H NMR (400 MHz,
1536, 1483, 1199, 985; HRMS (ESI): calcd for C12H13N3O2SNa [M+Na]+
DOI: 10.1039/C8OB00375K
286.0621, found 386.0621.
3-((Ethyl(methyl)(oxo)-λ6-sulfaneylidene)amino)quinoxalin-
DMSO-d6): δ 12.05 (s, 1H), 8.32−8.29 (m, 1H), 7.72−7.70 (m, 2H),
7.64−7.61 (m, 1H), 7.19−7.09 (m, 1H), 7.03−6.99 (m, 1H), 6.92 (d, J =
7.6 Hz, 1H), 3.66 (s, 3H); 13C NMR (100 MHz, DMSO-d6): δ 152.8,
152.5, 136.2, 134.8, 132.4, 131.7, 131.2, 130.1, 129.9, 128.1, 125.9,
125.2, 122.7, 114.6, 42.5; IR (neat, cm-1): ν = 3449, 2925, 1670, 1537,
1484, 1305, 1110, 997; HRMS (ESI): calcd for C15H12ClN3O2SNa
[M+Na]+ 356.0231, found 356.0239.
2(1H)-one (3m). Off-white solid (106 mg, 42% yield); m. p. =
163.0−163.7 °C; 1H NMR (400 MHz, DMSO-d6): δ 12.03 (s, 1H),
7.42−7.40 (m, 1H), 7.23−7.19 (m, 1H), 7.17−7.10 (m, 2H), 3.66 (q, J =
7.6 Hz, 2H), 3.44 (s, 3H), 1.32 (t, J = 7.6 Hz, 3H); 13C NMR (100 MHz,
DMSO-d6): δ 154.1, 152.9, 131.8, 130.0, 125.4(2C), 122.8, 114.6,
47.9, 38.1, 7.0; IR (neat, cm-1): ν = 3408, 2921, 1674, 1531, 1481,
1199, 1007, 962 HRMS (ESI): calcd for C11H13N3O2SNa [M+ Na]+
3-(((4-chlorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)amino)qui
274.0621, found 274.0626.
noxalin-2(1H)-one (3h). Off-white solid (234 mg, 70% yield); m.p. =
3-(((4-Bromophenyl)(methyl)(oxo)-λ6-
1
171.7−172.5 °C; H NMR (400 MHz, DMSO-d6): δ 12.08 (s, 1H), 8.08
sulfaneylidene)amino)-1-ethylquinoxalin-2(1H)-one (4a). Yellow
solid (402 mg, 99% yield); m.p. = 165.9−166.7 °C; 1H NMR (400 MHz,
DMSO-d6): δ 8.01 (d, J = 8.4 Hz, 2H), 7.88 (d, J = 8.4 Hz, 2H), 7.41 (d,
(d, J = 8.8, 2H), 7.73 (d, J = 8.8, 2H), 7.21−7.17 (m, 2H), 7.14−7.12 (m,
1H), 7.09−7.05 (m, 1H), 3.65 (s, 3H); 13C NMR (100 MHz, DMSO-d6): δ
153.4, 152.7, 138.3, 138.1, 131.4, 130.1, 129.5, 129.4, 125.9, 125.4,
122.8, 114.6, 43.5; IR (neat, cm-1): ν = 3448, 2918, 1684, 1537, 1483,
1307, 995, 592; HRMS (ESI): calcd for C15H12ClN3O2SNa [M+Na]+
J = 8.4 Hz, 1H), 7.34 ̶ 7.30 (m, 1H), 7.24 (d, J = 7.6 Hz, 1H), 7.18−7.14
(m, 1H), 4.21 (q, J = 6.8 Hz, 2H), 3.66 (s, 3H), 1.20 (t, J = 6.8 Hz, 3H);
13C NMR (100 MHz, DMSO-d6): δ 152.2, 151.7, 138.6, 132.3, 132.0,
131.8, 130.1, 129.6, 129.4, 127.3, 126.4, 126.3, 123.1, 113.9, 43.5,
37.0, 12.3; IR (neat, cm-1): ν = 3304, 3073, 2923, 1645, 1601, 1568,
1486, 982; HRMS (ESI): calcd for C17H16BrN3O2SNa [M+Na]+ 428.0039,
356.0231, found 356.0234.
3-(((4-Bromophenyl)(methyl)(oxo)-λ6-
sulfaneylidene)amino)quinoxalin-2(1H)-one (3i). White solid (374
mg, 99% yield); m.p. = 159.7−160.5 °C; 1H NMR (400 MHz, DMSO-d6):
δ 12.07 (s, 1H), 7.99 (d, J = 8.0 Hz, 2H), 7.88 (d, J = 8.0 Hz, 2H),
7.22−7.17 (m, 2H), 7.13 ̶
7.06 (m, 2H), 3.64 (s, 3H); 13C NMR (100
MHz, DMSO-d6): δ 153.4, 152.7, 138.6, 132.3, 131.4, 130.1, 129.6,
127.3, 125.9, 125.4, 122.8, 114.6, 43.4; IR (neat, cm-1): ν = 3452,
2918, 1735, 1685, 1536, 1303, 995, 547; HRMS (ESI): calcd for
C15H12BrN3O2SNa [M+Na]+ 399.9726, found 399.9738.
3-(((4-Methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)amino)
quinoxalin-2(1H)-one (3j). White solid (263 mg, 80% yield); m.p. =
214.0−214.9 °C; 1H NMR (400 MHz, DMSO-d6): δ 12.03 (s, 1H), 7.99
(d, J = 8.8 Hz, 2H), 7.23−7.17 (m, 4H), 7.13−7.06 (m, 2H), 3.84 (s, 3H),
3.60 (s, 3H); 13C NMR (100 MHz, DMSO-d6): δ 162.9, 153.7, 152.8,
131.6, 130.3, 130.1, 129.7, 129.5, 125.7, 125.4, 122.7, 114.5, 55.8,
43.8; IR (neat, cm-1): ν = 3435, 2999, 2851, 1663, 1593, 1484, 1103,
998; HRMS (ESI): calcd for C16H15N3O3SNa [M+Na]+ 352.0726, found
found 428.0042.
3-(((4-Bromophenyl)(methyl)(oxo)-λ6-sulfaneylidene)amino)-1-
pentylquinoxalin-2(1H)-one (4b). White solid (336 mg, 75% yield);
1
m.p. = 134.3−135.1 °C; H NMR (400 MHz, DMSO-d6): δ 8.00 (d, J =
8.8 Hz, 2H), 7.87 (d, J = 8.8 Hz, 2H), 7.37 (d, J = 8.0 Hz, 1H), 7.32
̶ 7.28
(m, 1H), 7.24 7.21 (m, 1H), 7.16 7.12 (m, 1H), 4.16− 4.13 (m, 2H),
̶
̶
3.65 (s, 3H), 1.59−1.58 (m, 2H), 1.32−1.30 (m, 4H), 0.85 (t, J = 6.4 Hz,
3H); 13C NMR (100 MHz, DMSO-d6): δ 152.1, 151.9, 138.6, 132.3,
131.7, 130.3, 129.6, 127.2, 126.4, 126.2, 123.0, 114.0, 43.4, 41.7,
28.4, 26.5, 21.8, 13.8; IR (neat, cm-1): ν = 3003, 2915, 1653, 1571,
1467, 1242, 981, 817; HRMS (ESI): calcd for C20H22BrN3O2SNa
[M+Na]+ 470.0508, found 470.0510.
1-Benzyl-3-(((4-bromophenyl)(methyl)(oxo)-λ6-sulfaneylidene)
amino)quinoxalin-2(1H)-one (4c). Off-white solid (431 mg, 92%
1
yield); m.p. = 179.6−180.4 °C; H NMR (400 MHz, DMSO-d6): δ 8.05
352.0733.
(d, J = 8.4 Hz, 2H), 7.89 (d, J = 8.4 Hz, 2H), 7.32
̶
7.28 (m, 2H), 7.25
̶
3-((Methyl(4-nitrophenyl)(oxo)-λ6-sulfaneylidene)amino)quino
7.18 (m, 6H), 7.12 (t, J = 7.2, 1H), 5.51−5.39 (m, 2H), 3.69 (s, 3H); 13
C
xalin-2(1H)-one (3k). White solid (65 mg, 19% yield); m. p. =
NMR (100 MHz, DMSO-d6): δ 152.5, 152.3, 138.5, 136.0, 132.4, 131.8,
130.4, 129.6, 128.7, 127.3, 127.2, 126.7, 126.3, 126.1, 123.3, 114.6,
45.1, 43.5; IR (neat, cm-1): ν = 3005, 2921, 1731, 1657, 1340, 1040,
960, 747; HRMS (ESI): calcd for C22H18BrN3O2SNa [M+Na]+ 490.0195,
found 490.0200.
1
166.7−167.4 °C; H NMR (400 MHz, DMSO-d6): δ 12.10 (s, 1H), 8.45
(d, J = 8.8 Hz, 2H), 8.34 (d, J = 8.8 Hz, 2H), 7.21
̶ 7.18 (m, 1H),
7.16−7.10 (m, 2H), 7.07
̶
7.03 (m, 1H), 3.71 (s, 3H); 13C NMR (100
MHz, DMSO-d6): δ 153.1, 152.6, 150.1, 145.2, 131.2, 130.2, 129.4,
126.1, 125.4, 124.4, 122.8, 114.6, 43.2; IR (neat, cm-1): ν = 3124,
1733, 1681, 1532, 1481, 1302, 1086, 997; HRMS (ESI): calcd for
C15H13N4O4S [M+H]+ 345.0652, found 345.0658.
1-Allyl-3-(((4-bromophenyl)(methyl)(oxo)-λ6-sulfaneylidene)
amino)quinoxalin-2(1H)-one (4d). White solid (343 mg, 82% yield);
1
m.p. = 154.5−155.2 °C; H NMR (400 MHz, DMSO-d6): δ 8.01 (d, J =
3-((1-Oxidotetrahydro-1-λ6-thiophen-1-ylidene)amino)quinoxa
lin-2(1H)-one (3l). Off-white solid (150 mg, 57% yield); m. p. =
161.5−162.5 °C; 1H NMR (400 MHz, DMSO-d6): δ 12.04 (s, 1H), 7.42
8.4, 2H), 7.88 (d, J = 8.4, 2H), 7.28
1H), 7.17 7.13 (m, 1H), 5.95−5.85 (m, 1H), 5.15 (dd, J = 10.4, 1.2 Hz,
1H), 5.03 (dd, J = 17.6, 1.2 Hz, 1H), 4.88 4.77 (m, 2H), 3.66 (s, 3H);
13C NMR (100 MHz, DMSO-d6): δ 152.2, 151.9, 138.5, 132.3, 131.7,
131.6, 130.4, 129.6, 127.3, 126.3, 126.1, 123.2, 116.9, 114.5, 44.0,
43.4; IR (neat, cm-1): ν = 2917, 2849, 1644, 1466, 1297, 1052, 985,
̶ 7.27 (m, 2H), 7.23 (d, J = 8.0 Hz,
̶
̶
(d, J = 7.6 Hz, 1H), 7.24
̶ 7.20 (m, 1H), 7.16 ̶ 7.12 (m, 2H),3.70 ̶ 3.63
(m, 2H), 3.46−3.39 (m, 2H), 2.24−2.20 (m, 2H), 2.17−2.14 (m, 2H); 13
C
NMR (100 MHz, DMSO-d6): δ 154.4, 152.9, 131.8, 130.1, 125.5, 123.0,
115.1, 114.6, 52.6, 23.2; IR (neat, cm-1): ν = 3543, 3425, 2949, 1671,
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