6
Journal of Chemical Research 00(0)
J=8.2Hz, CH), 7.43 (1H, t, J=7.6Hz, CH), 6.81 (1H, s, J=7.8Hz, CH), 7.51 (2H, dd, J=13.8, 8.0Hz, 2CH), 7.46–
CH). 13C NMR (101MHz, CDCl3): δ=178.28 (Cq), 7.39 (2H, m, 2CH), 7.33 (2H, d, J=7.2Hz, 2CH), 6.50 (1H,
162.25 (Cq), 156.13 (Cq), 133.91 (CH), 132.33 (CH), s, CH), 2.49 (3H, s, CH3). 13C NMR (101MHz, CDCl3):
130.67 (CH), 127.68 (Cq), 126.29 (Cq), 125.72 (CH), δ=178.29 (Cq), 166.08 (Cq), 156.42 (Cq), 136.75 (Cq),
125.37 (CH), 123.94 (Cq), 118.03 (CH), 107.70 (CH). 133.74 (Cq), 132.56 (CH), 131.22 (CH), 130.68 (CH),
HRMS (ESI): m/z calcd for C15H10BrO2 [M+H]+: 129.16 (CH), 126.17 (CH), 125.70 (CH), 125.20 (CH),
300.9859; found: 300.9867.
123.74 (Cq), 118.01 (CH), 111.90 (CH), 20.52 (CH3).
2-(p-Tolyl)-4H-chromen-4-one (3ae): Product 3ae was HRMS (ESI): m/z calcd for C16H12NaO2 [M+Na]+:
obtained as a yellow solid (43mg, 92%); m.p.: 109–111°C. 259.0730; found: 259.0720.
1H NMR (400MHz, CDCl3): δ=8.23 (1H, d, J=8.0Hz,
2-(2-Methoxyphenyl)-4H-chromen-4-one (3aj): Product
CH), 7.82 (2H, d, J=8.0Hz, 2CH), 7.69 (1H, t, J=7.8Hz, 3aj was obtained as a yellow solid (48mg, 95%); m.p.:
CH), 7.56 (1H, d, J=8.4Hz, CH), 7.41 (1H, t, J=7.6Hz, 101–102°C. 1H NMR (400MHz, CDCl3): δ=8.23 (1H, dd,
CH), 7.32 (2H, d, J=8.0Hz, 2CH), 6.80 (1H, s, CH), 2.43 J=8.0, 1.6Hz, CH), 7.91 (1H, dd, J=7.8, 1.6Hz, CH),
(3H, s, CH3). 13C NMR (101MHz, CDCl3): δ=178.44 (Cq), 7.70–7.65 (1H, m, CH), 7.53 (1H, d, J=8.2Hz, CH), 7.51–
163.57 (Cq), 156.20 (Cq), 142.22 (Cq), 133.62 (CH), 129.73 7.45 (1H, m, CH), 7.40 (1H, t, J=7.6Hz, CH), 7.15 (1H, s,
(CH), 128.90 (CH), 126.19 (Cq), 125.63 (CH), 125.09 CH), 7.11 (1H, t, J=7.2Hz, CH), 7.05 (1H, d, J=8.4Hz,
(CH), 123.94 (Cq), 118.02 (CH), 106.93 (CH), 21.52 (CH3). CH), 3.94 (3H, s, CH3). 13C NMR (101MHz, CDCl3):
HRMS (ESI): m/z calcd for C16H13O2 [M+H]+: 237.0910; δ=178.89 (Cq), 160.84 (Cq), 157.96 (Cq), 156.46 (Cq),
found: 237.0914.
133.50 (CH), 132.38 (CH), 129.25 (CH), 125.58 (CH),
2-[4-(Trifluoromethyl)phenyl]-4H-chromen-4-one 124.87 (CH), 123.79 (Cq), 120.80 (Cq), 120.69 (CH),
(3af): Product 3af was obtained as a yellow solid (51mg, 118.00 (CH), 112.63 (CH), 111.72 (CH), 55.65 (CH3).
1
88%); m.p.: 139–141°C. H NMR (400MHz, CDCl3): HRMS (ESI): m/z calcd for C16H12NaO3 [M+Na]+:
δ=8.24 (1H, d, J=8.0Hz, CH), 8.05 (2H, d, J=8.2Hz, 275.0679; found: 275.0668.
2CH), 7.80 (2H, d, J=8.2Hz, 2CH), 7.74 (1H, t, J=7.8Hz,
2-(m-Tolyl)-4H-chromen-4-one (3ak): Product 3ak was
CH), 7.60 (1H, d, J=8.4Hz, CH), 7.45 (1H, t, J=7.6Hz, obtained as a yellow solid (36mg, 77%); m.p.: 108–110°C.
CH), 6.88 (1H, s, CH). 13C NMR (101MHz, CDCl3): 1H NMR (400MHz, CDCl3): δ=8.23 (1H, d, J=8.0Hz,
4
δ=178.17 (Cq), 161.58 (Cq), 156.17 (Cq), 135.16 (d, JC– CH), 7.76–7.66 (3H, m, 3CH), 7.58 (1H, d, J=8.4Hz, CH),
F =1.0Hz, Cq), 134.10 (Cq), 133.12 (d, 2JC–F =33.0Hz, CH), 7.45–7.38 (2H, m, 2CH), 7.35 (1H, d, J=7.6Hz, CH), 6.82
3
126.62 (CH), 126.03 (q, JC–F =3.8Hz, CH), 125.78 (CH), (1H, s, CH), 2.46 (3H, s, CH3). 13C NMR (101MHz,
125.54 (CH), 123.92 (Cq), 123.58 (d, 1JC–F =272.6Hz, Cq), CDCl3): δ=178.50 (Cq), 163.60 (Cq), 156.25 (Cq), 138.81
118.10 (CH), 108.73 (CH). HRMS (ESI): m/z calcd for (Cq), 133.69 (CH), 132.38 (CH), 131.70 (CH), 128.91 (Cq),
C16H10F3O2 [M+H]+: 291.0627; found: 291.0632. The 126.82 (CH), 125.66 (CH), 125.15 (CH), 124.00 (Cq),
NMR data agree with those in a literature report.44
123.48 (CH), 118.06 (CH), 107.54 (CH), 21.49 (CH3).
2-(4-Methoxyphenyl)-4H-chromen-4-one (3ag): Product HRMS (ESI): m/z calcd for C16H12NaO2 [M+Na]+:
3ag was obtained as a yellow solid (38mg, 75%); m.p.: 259.0730; found: 259.0719.
1
151–153°C. H NMR (400MHz, CDCl3): δ=8.23 (1H, d,
2-(3-Bromophenyl)-4H-chromen-4-one (3al): Product
J=8.0Hz, CH), 7.89 (2H, d, J=8.8Hz, 2CH), 7.69 (1H, t, 3al was obtained as a yellow solid (44mg, 73%); m.p.:
J=7.8Hz, CH), 7.55 (1H, d, J=8.4Hz, CH), 7.41 (1H, t, 90–92°C.1H NMR (400MHz, CDCl3): δ=8.23 (1H, d,
J=7.6Hz, CH), 7.03 (2H, d, J=8.8Hz, 2CH), 6.76 (1H, s, J=7.0Hz, CH), 8.08 (1H, s, CH), 7.83 (1H, d, J=8.0Hz,
CH), 3.89 (3H, s, CH3). 13C NMR (101MHz, CDCl3): CH), 7.75–7.69 (1H, m, CH), 7.67 (1H, d, J=8.0Hz, CH),
δ=178.34 (Cq), 163.40 (Cq), 162.38 (Cq), 156.15 (Cq), 7.59 (1H, d, J=8.4Hz, CH), 7.47–7.36 (2H, m, 2CH), 6.80
133.54 (CH), 127.98 (CH), 125.63 (CH), 125.05 (CH), (1H, s, CH). 13C NMR (101MHz, CDCl3): δ=178.17 (Cq),
123.98 (Cq), 123.88 (Cq), 117.93 (CH), 114.43 (CH), 106.14 161.64 (Cq), 156.13 (Cq), 134.41 (CH), 133.98 (CH),
(CH), 55.48 (CH3). HRMS (ESI): m/z calcd for C16H12NaO3 133.77 (CH), 130.53 (CH), 129.22 (Cq), 125.73 (CH),
[M+Na]+: 275.0679; found: 275.0685.
125.42 (CH), 124.81 (Cq), 123.89 (Cq), 123.22 (CH),
2-(2-Chlorophenyl)-4H-chromen-4-one (3ah): Product 118.08 (CH), 108.16 (CH). HRMS (ESI): m/z calcd for
3ah was obtained as a yellow solid (38mg, 74%); m.p.: C15H10BrO2 [M+H]+: 300.9859; found: 300.9869.
113–115°C. 1H NMR (400MHz, CDCl3): δ=8.26 (1H, d,
2-(tert-Butyl)-4H-chromen-4-one (3am): Product 3am
J=7.8Hz, CH), 7.71 (1H, t, J=7.6Hz, CH), 7.64 (1H, d, was obtained as a yellow solid (37mg, 91%); m.p.: 72–74°C.
J=7.0Hz, CH), 7.53 (2H, t, J=8.2Hz, 2CH), 7.49–7.38 1H NMR (400MHz, CDCl3): δ=8.18 (1H, d, J=8.0Hz, CH),
(3H, m, 3CH), 6.66 (1H, s, CH). 13C NMR (101MHz, 7.66 (1H, t, J=7.8Hz, CH), 7.46 (1H, d, J=8.4Hz, CH),
CDCl3): δ=178.13 (Cq), 162.63 (Cq), 156.57 (Cq), 133.91 7.38 (1H, t, J=7.6Hz, CH), 6.29 (1H, s, CH), 1.36 (9H, s,
(CH), 132.91 (Cq), 131.90 (Cq), 131.76 (CH), 130.79 (CH), 3CH3). 13C NMR (101MHz, CDCl3): δ=178.94 (Cq), 176.04
130.63 (CH), 127.07 (CH), 125.74 (CH), 125.33 (CH), (Cq), 156.44 (Cq), 133.43 (CH), 125.52 (CH), 124.78 (CH),
123.83 (Cq), 118.18 (CH), 112.99 (CH). HRMS (ESI): m/z 123.40 (Cq), 117.80 (CH), 106.65 (CH), 36.47 (Cq), 27.85
calcd for C15H9ClNaO2 [M+Na]+: 279.0183; found: (CH3). HRMS (ESI): m/z calcd for C13H14NaO2 [M+Na]+:
279.0184.
225.0886; found: 225.0891.
2-(o-Tolyl)-4H-chromen-4-one (3ai): Product 3ai was
2-(Thiophen-2-yl)-4H-chromen-4-one (3an): Product
obtained as a yellow oil (39mg, 83%). 1H NMR (400MHz, 3an was obtained as a yellow solid (40mg, 87%); m.p.:
1
CDCl3): δ=8.26 (1H, d, J=8.0Hz, CH), 7.70 (1H, t, 93–95°C. H NMR (400MHz, CDCl3): δ=8.21 (1H, dd,