The Journal of Organic Chemistry
Page 8 of 12
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7.83 (s, 1H), 7.56 (d, J = 7.8 Hz, 1H), 7.21 (d, J = 8.4 Hz,
(3C); HRMS (ESI): m/z calcd for C13H13N3NaOS [M +
Na ]+ : 282.0672, found: 282.0677.
1H), 1.61 (s, 9H); 13C{1H} NMR (100 MHz, DMSO-d6) δ:
163.1, 153.0, 133.2, 131.2, 129.5, 129.2, 117.9, 115.2, 47.3,
29.7 (3C); HRMS (ESI): m/z calcd for C12H14BrN2OS [M +
H ]+: 313.0005, found: 313.0003.
3-(Tert-butylthio)-6-chloroquinoxalin-2(1H)-one
(3v).
49% yield (65.6 mg, petroleum ether/ethyl acetate = 8:1 as
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an eluent). H NMR (400 MHz, DMSO-d6) δ 12.47 (s, 1H),
3-(Tert-butylthio)-6-(trifluoromethyl)quinoxalin-2(1H)-o
ne (3q). 54 % yield (81.5 mg, petroleum ether/ethyl acetate =
8:1 as an eluent). 1H NMR (400 MHz, DMSO-d6) δ 12.61 (s,
1H), 7.81 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 9.4 Hz, 2H), 1.61
(s, 9H); 13C{1H} NMR (101 MHz, DMSO-d6) δ: 164.8, 153.0,
134.2, 130.3, 128.2, 128.1 (q, J = 32.3 Hz), 124.3 (q, J =
273.2 Hz), 120.0 (q, J = 3.5 Hz), 113.1 (q, J = 4.1 Hz), 47.4,
29.6 (3C); HRMS (ESI): m/z calcd for C13H13F3N2NaOS [M
+ Na ]+:325.0593, found:325.0590.
7.64 (d, J = 8.2 Hz, 1H), 7.27 – 7.24 (m, 2H), 1.60 (s, 9H);
13C{1H} NMR (100 MHz, DMSO-d6) δ: 163.2, 153.0, 132.9,
129.1, 128.5, 127.5, 126.3, 117.6, 47.3, 29.7 (3C); HRMS
(ESI): m/z calcd for C12H13ClN2NaOS [M + Na ]+:291.0329,
found: 291.0315.
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3-(Tert-butylthio)-7-chloroquinoxalin-2(1H)-one
(3w).
45% yield (60.3 mg, petroleum ether/ethyl acetate = 8:1 as
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an eluent). H NMR (400 MHz, DMSO-d6) δ 12.47 (s, 1H),
7.47 (dd, J = 9.4, 2.6 Hz, 1H), 7.34 – 7.25 (m, 2H), 1.61 (s,
9H); 13C{1H} NMR (100 MHz, DMSO-d6) δ: 161.9, 152.9,
132.5, 131.2, 131.1, 128.8, 123.8, 115.2, 47.1, 29.7 (3C);
HRMS (ESI): m/z calcd for C12H13ClN2NaOS [M + Na ]+ :
291.0329, found: 291.0322.
3-(Tert-butylthio)-7-(trifluoromethyl)quinoxalin-2(1H)-o
ne (3r). 51% yield (77.0 mg, petroleum ether/ethyl acetate =
8:1 as an eluent). 1H NMR (400 MHz, DMSO-d6) δ 12.71 (s,
1H), 7.94 (s, 1H), 7.73 (d, J = 8.5 Hz, 1H), 7.43 (d, J = 8.5
Hz, 1H), 1.63 (s, 9H); 13C{1H} NMR (101 MHz, DMSO-d6)
δ: 163.6, 153.3, 133.1, 131.6, 127.2 (q, J = 271.7 Hz), 124.8
(q, J = 3.6 Hz), 124.2 (q, J = 4.0 Hz), 123.9 (q, J = 32.6 Hz),
117.2, 47.4, 29.7 (3C); HRMS (ESI): m/z calcd for
C13H13F3N2NaOS [M + Na ]+ : 325.0593, found: 325.0599.
3-(Tert-butylthio)-6,7-dichloroquinoxalin-2(1H)-one (3s).
52% yield (78.5 mg, petroleum ether/ethyl acetate = 8:1 as
3-(Tert-butylthio)-6-fluoroquinoxalin-2(1H)-one
(3x).
51% yield (63.7 mg, petroleum ether/ethyl acetate = 8:1 as
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an eluent). H NMR (400 MHz, DMSO-d6) δ 12.53 (s, 1H),
7.71 (d, J = 2.2 Hz, 1H), 7.48 – 7.45 (m, 1H), 7.27 (d, J = 8.7
Hz, 1H), 1.62 (s, 9H); 13C{1H} NMR (101 MHz, DMSO-d6)
δ 163.2, 158.5 (d, J = 239.5 Hz), 152.9, 132.6 (d, J = 11.9
Hz), 126.9, 117.3 (d, J = 9.3 Hz), 116.4 (d, J = 24.3 Hz),
112.5 (d, J = 22.8 Hz), 47.2, 29.7 (3C); HRMS (ESI): m/z
calcd for C12H13FN2NaOS [M + Na ]+: 275.0625, found:
275.0617.
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an eluent). H NMR (400 MHz, DMSO-d6) δ 12.53 (s, 1H),
7.85 (s, 1H), 7.36 (s, 1H), 1.60 (s, 9H); 13C{1H} NMR (100
MHz, DMSO-d6) δ: 163.6, 152.8, 131.7, 130.3, 130.1, 128.0,
125.5, 116.9, 47.4, 29.7 (3C); HRMS (ESI): m/z calcd for
C12H12Cl2N2NaOS [M + Na ]+: 324.9940, found: 324.9944.
3-(Tert-butylthio)-2-oxo-1,2-dihydroquinoxaline-6-carbo
nitrile (3t). 51% yield (66.1 mg, petroleum ether/ethyl
acetate = 8:1 as an eluent). 1H NMR (400 MHz, DMSO-d6) δ
12.74 (s, 1H), 8.13 (s, 1H), 7.789 – 7.76 (m, 1H), 7.36 (d, J =
8.4 Hz, 1H), 1.62 (s, 9H); 13C{1H} NMR (100 MHz,
DMSO-d6) δ: 165.5, 152.9, 134.5, 130.6, 128.3, 126.9, 120.0,
118.9, 110.0, 47.6, 29.6 (3C); HRMS (ESI): m/z calcd for
C13H13N3NaOS [M + Na ]+: 282.0672, found: 282.0671.
2-(Tert-butylthio)-3-oxo-3,4-dihydroquinoxaline-6-carbo
nitrile (3u). 54% yield (69.9 mg, petroleum ether/ethyl
acetate = 8:1 as an eluent).1H NMR (400 MHz, DMSO-d6) δ
12.64 (s, 1H), 7.78 (s, 1H), 7.61 (d, J = 23.2 Hz, 2H), 1.63 (s,
9H); 13C{1H} NMR (100 MHz, DMSO-d6) δ: 163.8, 153.1,
133.9, 131.8, 131.6, 131.4, 118.9, 117.3, 105.9, 47.5, 29.7
3-(Tert-butylthio)-6,7-dimethylquinoxalin-2(1H)-one (3y).
23% yield (30.3 mg, petroleum ether/ethyl acetate = 8:1 as
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an eluent). H NMR (400 MHz, DMSO-d6) δ 12.26 (s, 1H),
7.43 (s, 1H), 7.01 (s, 1H), 2.27 (s, 6H), 1.61 (s, 9H); 13C{1H}
NMR (100 MHz, DMSO-d6) δ: 159.9, 153.3, 127.9, 132.4,
130.9, 128.0, 127.3, 116.0, 46.7, 29.8 (3C), 20.1, 19.3;
HRMS (ESI): m/z calcd for C14H19N2OS [M + H ]+
263.1213, found: 263.1204.
:
1-Benzyl-3-(tert-butylthio)quinoxalin-2(1H)-one
(3z).
30% yield (48.6 mg, petroleum ether/ethyl acetate = 40:1 as
an eluent). 1H NMR (400 MHz, DMSO-d6) δ 7.73 (d, J = 7.6
Hz, 1H), 7.42 (d, J = 4 Hz, 2H), 7.34 – 7.30 (m, 3H), 7.26 –
7.24 (m, 3H), 5.48 (s, 2H), 1.65 (s, 9H). 13C{1H} NMR (100
MHz, DMSO-d6) δ: 160.4, 153.0, 136.1, 133.1, 130.5, 129.2
(2C), 128.9, 128.2, 127.9, 127.3 (2C), 124.3, 115.6, 47.3,
45.7, 29.7 (3C); HRMS (ESI): m/z calcd for C19H20N2NaOS
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