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Organic & Biomolecular Chemistry
Page 5 of 8
DOI: 10.1039/C8OB01398E
Journal Name
ARTICLE
156.24, 153.38, 135.35,134.29, 134.22, 134.09, 133.72, 130.16, Following the general procedure, isolated yield (304.2 mg, 87%)
128.77, 127.70, 127.42, 126.58, 126.14, 126.09, 125.41, 122.72,
118.01; HRMS (ESI-TOF) m/z calculated for C19H12NaO2Se+
374.9895 (M+Na)+, found 374.9892.
as a colorless oil; IR: 3042,2936,2359,1633,1479,1314
cm-1; 1H-NMR (CDCl3, 400 MHz): δ (ppm) 8.11 (s, 1H), 8.07 - 8.01
(m, 1H), 7.55 - 7.49 (m, 2H), 7.45 (dt, J = 7.3, 1.5 Hz, 1H), 7.38 (d,
J = 8.6 Hz, 1H), 7.29 - 7.18 (m, 2H), 2.47 (s, 3H)
100 MHz) 175.02, 157.27, 154.68, 135.89, 135.26, 134.95,
;
13C-NMR (CDCl3,
3-((4-Methoxyphenyl)selanyl)-4H-chromen-4-one (3ad)
Following the general procedure, isolated yield (248.3 mg, 75%)
:
132.28, 130.78, 130.72, 130.35, 127.91, 125.74, 123.07, 117.88,
116.27, 20.97; HRMS (ESI-TOF) m/z calculated for C16H11NaO2Se+
372.9505 (M+Na)+, found 372.9496.
as a colorless oil; IR: 3072,2932,1642,1490,1245,756
cm-1; 1H-NMR (CDCl3, 400 MHz): δ (ppm)8.24 (dd, J = 8.2, 1.7 Hz,
1H), 7.70 - 7.59 (m, 4H), 7.41 (dtd, J = 8.1, 3.4, 1.1 Hz, 2H), 6.92 -
6.85 (m, 2H), 3.82 (s, 3H)
; :175.28,
13C-NMR (CDCl3, 100 MHz)
6-Chloro-7-methyl-3-(o-tolylselanyl)-4H-chromen-4-one (3dh)
Following the general procedure, isolated yield (283.7 mg, 78%)
as a colorless oil; IR: 3062, 2928, 1627, 1452, 1076, 754 cm-1; 1H-
NMR (CDCl3, 400 MHz): δ (ppm) 8.20 (s, 1H), 7.63 (s, 1H), 7.49
(dd, J = 7.7, 1.2 Hz, 1H), 7.35 - 7.23 (m, 3H), 7.12 (td, J = 7.3, 2.1
160.23, 156.30, 153.86, 137.11, 133.67, 126.19, 125.38, 122.90,
119.38, 118.01, 117.08, 115.37, 55.33; HRMS (ESI-TOF) m/z
calculated for C16H12NaO3Se+ 354.9844(M+Na)+, found 354.9868.
6-Chloro-3-(p-tolylselanyl)-4H-chromen-4-one (3be)
Following the general procedure, isolated yield (245.0 mg, 70%)
Hz, 1H), 2.51 (d, J = 1.9 Hz, 6H); :δ
13C-NMR (CDCl3, 100 MHz)
174.17, 154.66, 154.41, 143.17, 140.72, 134.63, 132.19, 130.54,
128.69, 128.26, 127.07, 125.82, 121.95, 119.82, 117.33, 22.37,
20.82; HRMS (ESI-TOF) m/z calculated for C17H13ClNaO2Se+
386.9662(M+Na)+, found 386.9712.
as a colorless oil; IR: 3057,1650,1467,1303,1079,825,
810 cm-1 1H-NMR (CDCl3, 400 MHz): δ (ppm) 8.20 (d, J = 2.6
;
Hz, 1H), 7.74 (s, 1H), 7.62 (d, J = 2.6 Hz, 1H), 7.55 (d, J = 8.1 Hz,
2H), 7.40 (d, J = 8.9 Hz, 1H), 7.16 (d, J = 7.8 Hz, 2H), 2.37 (s, 3H)
13C-NMR (CDCl3, 100 MHz)
:δ 174.13, 154.64, 154.52,
6-Chloro-7-methyl-3-(phenylselanyl)-4H-chromen-4-one (3da)
Following the general procedure, isolated yield (258.7 mg, 74%)
;
138.78, 134.89, 133.96, 131.36, 130.51, 125.60, 123.81, 123.42,
119.78, 118.95, 21.20; HRMS (ESI-TOF) m/z calculated for
1
as a colorless oil; IR: 2359, 1645, 1406, 1283, 735, 689 cm-1; H-
16H11ClNaO2Se+ 372.9505 (M+Na)+, found 372.9496.
NMR (CDCl3, 400 MHz)
:δ 8.19 (s, 1H), 7.84 (s, 1H), 7.67 - 7.55
C
(m, 2H), 7.39 - 7.25 (m, 4H), 2.50 (d, J = 0.8 Hz, 3H); 13C-NMR
(CDCl3, 100 MHz): δ 174.06, 155.45, 154.61, 143.22, 133.98,
132.23, 129.59, 128.25, 127.89, 125.88, 122.11, 119.83, 117.87,
6-Chloro-3-((4-fluorophenyl)selanyl)-4H-chromen-4-one (3bf)
Following the general procedure, isolated yield (244.0 mg, 69%)
20.83; HRMS (ESI-TOF) m/z calculated for
372.9505(M+Na)+, found 372.9496.
C
16H11ClNaO2Se+
as a colorless oil; IR: 3057
759 cm-1 1H-NMR (CDCl3, 400 MHz): δ (ppm) 8.20 (d, J = 2.7
Hz, 1H), 7.86 (s, 1H), 7.64 (qd, J = 6.9, 6.3, 2.3 Hz, 3H), 7.42 (d, J =
8.9 Hz, 1H), 7.04 (t, J = 8.7 Hz, 2H)
13C-NMR (CDCl3, 100 MHz)
δ 174.05, 163.10 (d, JC-F,= 248 Hz), 155.24, 154.66, 136.74 d,
, 134.14, 131.56, 125.65, 123.93, 122.05, 119.83,
,2926,1634,1489,1464,1081
,
;
3-(Phenylthio)-4H-chromen-4-one (4aa)
Following the general procedure, isolated yield (228.6 mg, 90%)
as a colorless oil; IR: 3058, 2925, 1653, 1612, 1464, 1309, 1113,
;
:
(
JC-F,= 8 Hz
)
760 cm-1
; ,400 MHz): δ(ppm)8.27 (dd, J =
1H-NMR (CDCl3
118.38, 116.87 ( d, JC-F,= 22 Hz ) ; HRMS (ESI-TOF) m/z
calculated for C15H9ClFO2Se+ 354.9440 (M+H)+, found 354.9258.
8.0, 1.7 Hz, 1H), 8.18 (s, 1H), 7.72 (ddd, J = 8.7, 7.1, 1.7 Hz, 1H),
7.50 (dd, J = 8.5, 1.0 Hz, 1H), 7.50 - 7.38 (m, 3H), 7.35 - 7.20 (m,
3H)
; ,100MHz):δ175.07, 157.36, 156.35,
13C-NMR (CDCl3
3-((4-Methoxyphenyl)selanyl)-6-methyl-4H-chromen-4-one
(3cd)
Following the general procedure, isolated yield (251.9 mg, 73%)
as a colorless oil; IR: 3057, 2920, 1644, 1485, 1025, 819 cm-1; 1H-
NMR (CDCl3, 400 MHz):δ 8.05 - 7.95 (m, 1H), 7.72 - 7.56 (m,
3H), 7.46 (dd, J = 8.5, 2.2 Hz, 1H), 7.30 (d, J = 8.6 Hz, 1H), 6.87 (d,
J = 8.7 Hz, 2H), 3.81 (s, 3H), 2.45 (s, 3H); 13C-NMR (CDCl3, 100
MHz): δ 175.34, 160.16, 154.60, 153.98, 136.98, 135.41, 134.96,
125.41, 122.60, 118.98, 117.76, 117.31, 115.32, 55.32, 20.95.
HRMS (ESI-TOF) m/z calculated for C17H14NaO3Se+ 369.0000
(M+Na)+, found 368.9995.
134.00, 129.85, 129.80, 129.20, 127.12, 126.47, 125.75, 123.68,
119.95, 118.16; HRMS (ESI-TOF) m/z calculated for C15H11O2S+
277.0294 (M+H)+, found 277.0287.
3-(p-Tolylthio)-4H-chromen-4-one (4ae)
Following the general procedure, isolated yield (235.8 mg, 88%)
as a colourless oil; IR: 3075, 2923, 2359, 1647, 1464, 1114, 758
cm-1; H-NMR (CDCl3
1
,400 MHz) :δ(ppm) 8.26 (dd, J = 8.0,
1.7 Hz, 1H), 8.07 (s, 1H), 7.70 (ddd, J = 8.7, 7.1, 1.7 Hz, 1H), 7.52 -
7.41 (m, 2H), 7.40 - 7.33 (m, 2H), 7.13 (d, J = 7.9 Hz, 2H), 2.33 (s,
3H)
133.89
121.10, 118.11, 21.11; HRMS (ESI-TOF) m/z calculated for
16H12NaO2S+ 291.0450 (M+Na)+, found 291.0478.
;
13C-NMR (CDCl3
2C
,
100 MHz,)
:δ 175.09, 156.26, 137.60,
(
), 130.99, 130.06, 129.82, 126.40, 125.61, 123.57,
6-Methyl-3-(p-tolylselanyl)-4H-chromen-4-one (3ce)
Following the general procedure, isolated yield (296.1mg, 90%)
C
as a colorless oil; IR: 3059
757 cm-1 1H-NMR (CDCl3, 400 MHz): δ (ppm) 8.00 (d, J = 2.2
Hz, 1H), 7.77 (s, 1H), 7.55 - 7.42 (m, 3H), 7.30 (d, J = 8.6 Hz, 1H),
7.11 (d, J = 7.8 Hz, 2H), 2.44 (s, 3H), 2.33 (s, 3H)
13C-NMR
(CDCl3, 100 MHz) δ 175.32, 154.96, 154.62, 138.37, 135.50,
,2918,2362,1645,1483,1312
,
;
3-((4-Chlorophenyl)thio)-4H-chromen-4-one (4ab)
Following the general procedure, isolated yield (172.8 mg, 60 %)
;
as a colourless oil; IR: 3051,1648
827
758 cm-1 1H-NMR(CDCl3
,
,
1478
,
400 MHz,)
1465,
:
1313
,
ppm
1091
,
8.26
:
,
;
δ
(
)
135.01, 134.46, 130.38, 125.52, 124.12, 122.74, 118.18, 117.78,
21.19, 20.97;HRMS (ESI-TOF) m/z calculated for C17H14NaO2Se+
353.0051 (M+Na)+, found 353.0027.
(q, J = 3.4, 2.6 Hz, 2H), 7.73 (ddd, J = 8.6, 7.1, 1.7 Hz, 1H), 7.56 -
7.43 (m, 2H), 7.37 - 7.22 (m, 4H) 100 MHz)
13C-NMR (CDCl3
δ 174.95, 157.91, 156.35, 134.17, 133.10, 132.80, 130.88,
;
,
:
129.27, 126.45, 125.91, 123.72, 119.22, 118.21;HRMS (ESI-TOF)
3-((3-Chlorophenyl)selanyl)-6-methyl-4H-chromen-4-one (3cg)
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J. Name., 2013, 00, 1-3 | 5
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