Page 9 of 13
The Journal of Organic Chemistry
MHz, CDCl3): δ 193.0, 140.1, 134.4, 133.9. 131.9, 130.8, 142.6, 138.2, 131.6, 130.1, 129.4, 128.9, 128.4, 126.6,
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129.9, 129.3, 129.0, 128.9, 125.8, 112.2, 111.6, 54.8,
26.9, 21.5 ppm; IR (neat, cm−1): 3385, 3063, 3026, 2918,
2257, 2209, 1680, 1597, 1449, 1260, 753, 691; LRMS
(ESI): m/z = 297 [M+H] HRMS (ESI) Calcd for
C18H14N2NaO: 297.0998. Found 297.0998.
126.1, 124.7, 121.7, 111.5, 108.0 ppm.21
3-Benzoylcyclohexanone (3pb). Yield 26% (2.6 mg),
colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.95 (d, J =
7.6 Hz, 2H), 7.60 (t, J = 7.2 Hz, 1H), 7.49 (t, J = 7.6 Hz,
2H), 3.90–3.75 (m, 1H), 2.73 (dd, J = 14.4, 11.0 Hz, 1H),
2.54–2.30 (m, 3H), 2.20–2.05 (m, 2H), 1.95–1.78 (m, 2H)
ppm; 13C{1H} NMR (100 MHz, CDCl3): δ 210.2, 200.4,
135.4, 133.5, 128.9, 128.4, 45.2, 43.2, 41.0, 28.4, 24.8
ppm.22
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2-[1-(2-Methylphenyl)-2-oxo-2-
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phenylethyl]propanedinitrile (3lb). Yield 63% (8.6 mg),
colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.77 (d, J =
8.4 Hz, 2H), 7.54 (t, J = 7.6 Hz, 1H), 7.45–7.23 (m, 4H),
7.16 (t, J = 7.6 Hz, 1H), 7.02 (d, J = 8.0 Hz, 1H), 5.34 (d,
J = 8.8 Hz, 1H), 4.52 (d, J = 8.8 Hz, 1H), 2.71 (s, 3H)
ppm; 13C{1H} NMR (100 MHz, CDCl3): δ 193.7, 136.3,
134.4, 134.0, 132.3, 130.7, 129.9, 129.0, 128.8, 127.7,
127.2, 112.2, 111.6, 50.8, 26.1, 20.0 ppm; IR (neat, cm−1):
3375, 2916, 2257, 2209, 1680, 1449, 1256, 753, 689;
LRMS (ESI): m/z = 297 [M+H] HRMS (ESI) Calcd for
C18H14N2NaO: 297.0998. Found 297.1006.
2-[2-Oxo-2-(4-methylphenyl)-1-
phenylethyl]propanedinitrile (3ag). Yield 67% (9.2 mg),
colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J =
8.4 Hz, 2H), 7.45–7.30 (m, 5H), 7.20 (d, J = 8.0 Hz, 2H),
5.08 (d, J = 8.4 Hz, 1H), 4.53 (d, J = 8.4 Hz, 1H), 2.36 (s,
3H) ppm; 13C{1H} NMR (100 MHz, CDCl3): δ 192.6,
145.7, 132.3, 131.4, 130.0, 129.8, 129.7, 129.4, 128.6,
112.2, 111.6, 54.7, 26.8, 21.8 ppm; IR (neat, cm−1): 3032,
2918, 2257, 1680, 1605, 1455, 1262, 1177, 756, 704;
LRMS (ESI): m/z = 297 [M+H] HRMS (ESI) Calcd for
C18H14N2ONa: 297.0998. Found 297.0997.
2-(1-Benzoyl-2,2-dimethylpropyl)propanedinitrile
(3mb). Yield 26% (3.1 mg), colorless oil. 1H NMR (400
MHz, CDCl3): δ 7.96 (dd, J = 10.0, 4.0 Hz, 2H), 7.66 (td,
J = 8.0, 1.2 Hz, 1H), 7.53 (t, J = 8.0 Hz, 2H), 4.28 (d, J
= 8.0 Hz, 1H), 4.07 (d, J = 8.0 Hz, 1H), 1.14 (s, 9H) ppm;
13C{1H} NMR (100 MHz, CDCl3): δ = 198.2, 137.4,
134.4, 129.1, 128.6, 113.2, 112.5, 54.1, 34.8, 28.6, 22.3
ppm.7
2-[2-Oxo-2-(4-bromophenyl)-1-
phenylethyl]propanedinitrile (3ah). Yield 62% (10.5
mg), colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.75 (d,
J = 8.8 Hz, 2H), 7.55 (d, J = 8.8 Hz, 2H), 7.50–7.28 (m,
5H), 5.04 (d, J = 8.0 Hz, 1H), 4.51 (d, J = 8.4 Hz, 1H)
ppm; 13C{1H} NMR (100 MHz, CDCl3): δ 192.1, 132.5,
131.7, 131.3, 130.6, 130.2, 130.1, 130.0, 128.6, 120.0,
111.3, 54.9, 26.8 ppm; IR (neat, cm−1): 2918, 1682, 1586,
1399, 1256, 1071, 1009, 755, 701; LRMS (ESI): m/z =
361 [M+H] HRMS (ESI) Calcd for C17H11BrN2ONa:
360.9947. Found 360.9947.
1,3-Dimethyl-5-(2-oxo-1,2-diphenylethyl)-
2,4,6(1H,3H,5H)-pyrimidinetrione (3nb). Yield 60%
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(10.5 mg), colorless oil. H NMR (400 MHz, CDCl3): δ
7.79 (d, J = 7.2 Hz, 2H), 7.48 (t, J = 7.4 Hz, 1H), 7.37–
7.20 (m, 7H), 5.82 (d, J = 3.2 Hz, 1H), 3.83 (d, J = 3.2
Hz, 1H), 3.33 (s, 3H), 3.30 (s, 3H) ppm; 13C{1H} NMR
(100 MHz, CDCl3): δ 198.1, 167.7, 167.1, 151.5, 137.0,
134.9, 133.6, 130.2, 129.4, 128.59, 128.58, 127.7, 56.7,
51.4, 28.9, 28.6 ppm.7
2-(2-Oxo-1-phenylpropyl)propanedinitrile (3ai). Yield
88% (8.7 mg), colorless oil. 1H NMR (400 MHz, CDCl3):
δ 7.51–7.45 (m, 3H), 7.30–7.24 (m, 2H), 4.37 (d, J = 8.4
Hz, 1H), 4.26 (d, J = 8.4 Hz, 1H), 2.18 (s, 3H) ppm;
13C{1H} NMR (100 MHz, CDCl3): δ 201.4, 131.0, 130.2,
130.1, 128.7, 111.9, 111.3, 59.0, 28.3, 25.5 ppm; IR (neat,
cm−1): 2916, 1715, 1360, 1165, 756, 701; LRMS (ESI):
2-Benzoyl-1,4-dihydroxynaphthalene (3ob). Yield 70%
1
(9.2 mg), colorless oil. H NMR (400 MHz, CDCl3): δ
13.56 (s, 1H), 8.52 (d, J = 8.0 Hz, 1H), 8.13 (d, J = 8.4
Hz, 1H), 7.77–7.40 (m, 7H), 6.86 (s, 1H), 5.10 (brs, 1H)
ppm; 13C{1H} NMR (100 MHz, CDCl3): δ 200.9, 158.8,
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