The Journal of Organic Chemistry
Article
+
104.9, 88.0, 51.1, 36.7, 33.0, 31.5. 19F NMR (376 MHz, DMSO-d6) δ
(ESI-TOF): m/z [M + H]+ calcd for C24H17F3NO4 : 440.1104;
found: 440.1102.
+
−114.04. HRMS (ESI-TOF): m/z [M + H]+ calcd for C23H17FNO3 :
374.1187; found: 374.1192.
4-Benzoyl-2-hydroxy-2-(4-(methylthio)phenyl)-5-phenyl-1,2-di-
hydro-3H-pyrrol-3-one (3u). Yield 82%; 329.2 mg; yellow solid; mp
195−197 °C; 1H NMR (400 MHz, DMSO-d6) δ 10.42 (s, 1H),
7.62−7.54 (m, 6H), 7.49−7.45 (m, 3H), 7.37−7.30 (m, 1H), 2.48 (s,
1H). 13C{1H} NMR (100 MHz, DMSO-d6) δ 195.2, 189.2, 178.9,
139.2, 138.4, 134.6, 131.9, 131.8, 130.3, 129.1, 128.6, 128.3, 127.7,
126.1, 125.7, 105.0, 88.2, 14.7. HRMS (ESI-TOF): m/z [M + H]+
calcd for C24H20NO3S+: 402.1158; found: 402.1164.
4-Benzoyl-2-(4-bromophenyl)-2-hydroxy-5-phenyl-1,2-dihydro-
3H-pyrrol-3-one (3m). Yield 83%; 360.5 mg; white solid; mp 232−
234 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.55 (s, 1H), 7.74−7.68
(m, 7H), 7.60−7.56 (m, 3H), 7.52−7.48 (m, 3H), 7.41−7.38 (m,
2H). 13C{1H} NMR (100 MHz, DMSO-d6) δ 195.0, 189.3, 179.2,
139.2, 137.6, 132.0, 131.9, 131.4, 130.3, 129.2, 128.7, 128.4, 127.9,
127.8, 121.8, 105.1, 88.1. HRMS (ESI-TOF): m/z [M + H]+ calcd for
+
2-([1,1′-Biphenyl]-4-yl)-4-benzoyl-2-hydroxy-5-phenyl-1,2-dihy-
C23H17BrNO3 : 434.0386; found: 434.0383.
dro-3H-pyrrol-3-one (3v). Yield 83%; 358.1 mg; white solid; mp
4-Benzoyl-2-(4-chlorophenyl)-2-hydroxy-5-phenyl-1,2-dihydro-
3H-pyrrol-3-one (3n). Yield 85%; 331.4 mg; white solid; mp 243−
245 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.51 (s, 1H), 7.67−7.62
(m, 5H), 7.60−7.56 (m, 3H), 7.52−7.47 (m, 5H), 7.39−7.35 (m,
2H). 13C{1H} NMR (100 MHz, DMSO-d6) δ 194.9, 189.2, 179.1,
139.1, 137.1, 133.1, 132.0, 131.9, 130.3, 129.2, 128.7, 128.45, 128.41,
127.8, 127.5, 105.0, 88.0. HRMS (ESI-TOF): m/z [M + H]+ calcd for
1
227−229 °C. H NMR (400 MHz, DMSO-d6) δ 10.52 (s, 1H), 7.75
(d, J = 8.4 Hz, 2H), 7.71−7.64 (m, 8H), 7.60−7.56 (m, 2H), 7.52−
7.47 (m, 5H), 7.39−7.36 (m, 3H). 13C{1H} NMR (100 MHz,
DMSO-d6) δ 195.2, 189.2, 179.0, 140.2, 139.7, 139.2, 137.3, 131.9,
131.8, 130.4, 129.1, 129.0, 128.8, 128.6, 128.4, 127.8, 127.6, 126.7,
126.2, 105.1, 88.4. HRMS (ESI-TOF): m/z [M + H]+ calcd for
+
+
C29H22NO3 : 432.1594; found: 432.1598.
C23H17ClNO3 : 390.0891; found: 390.0897.
4-Benzoyl-2-hydroxy-2-(naphthalen-1-yl)-5-phenyl-1,2-dihydro-
4-Benzoyl-2-(3-chlorophenyl)-2-hydroxy-5-phenyl-1,2-dihydro-
3H-pyrrol-3-one (3o). Yield 81%; 315.8 mg; white solid; mp 189−
191 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.52 (s, 1H), 7.72−7.62
(m, 6H), 7.57 (d, J = 6.8 Hz, 1H), 7.51−7.48 (m, 6H), 7.40−7.36 (m,
2H). 13C{1H} NMR (100 MHz, DMSO-d6) δ 194.8, 189.2, 179.3,
140.6, 139.1, 133.2, 132.1, 131.9, 130.4, 130.2, 129.2, 128.7, 128.4,
127.8, 125.7, 124.1, 112.1, 105.1, 87.8. HRMS (ESI-TOF): m/z [M +
3H-pyrrol-3-one (3w). Yield 81%; 328.4 mg; white soild; mp 224−
1
226 °C. H NMR (400 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.05 (s,
1H), 7.98 (s, 1H), 7.76 (d, J = 7.6 Hz, 2H), 7.55−7.47 (m, 10H),
7.42−7.38 (m, 3H). 13C{1H} NMR (100 MHz, DMSO-d6) δ 194.4,
189.0, 179.5, 139.3, 138.1, 132.0, 131.9, 131.8, 130.6, 130.1, 129.80,
129.75, 129.2, 128.4, 127.8, 107.7, 85.4. HRMS (ESI-TOF): m/z [M
+
+ H]+ calcd for C27H20NO3 : 406.1438; found: 406.1438.
+
H]+ calcd for C23H17ClNO3 : 390.0891; found: 390.0895.
4-Benzoyl-2-hydroxy-2-(naphthalen-2-yl)-5-phenyl-1,2-dihydro-
4-Benzoyl-2-(3-bromophenyl)-2-hydroxy-5-phenyl-1,2-dihydro-
3H-pyrrol-3-one (3x). Yield 80%; 324.4 mg; pink soild; mp 220−222
3H-pyrrol-3-one (3p). Yield 87%; 377.8 mg; white solid; mp 117−
1
1
°C. H NMR (400 MHz, DMSO-d6) δ 10.59 (s, 1H), 8.17 (s, 1H),
119 °C. H NMR (400 MHz, DMSO-d6) δ 10.45 (s, 1H), 7.68 (s,
8.04−7.93 (m, 3H), 7.68 (d, J = 3.2 Hz, 6H), 7.61−7.46 (m, 6H),
7.38−7.35 (m, 2H). 13C{1H} NMR (100 MHz, DMSO-d6) δ 195.3,
189.3, 179.1, 139.2, 135.6, 132.8, 132.7, 131.9, 131.8, 130.4, 129.2,
128.7, 128.4, 128.3, 128.1, 127.8, 127.5, 126.4, 124.6, 123.4, 105.2,
1H), 7.65 (s, 1H), 7.61−7.52 (m, 6H), 7.46−7.43 (m, 4H), 7.38−
7.31 (m, 3H). 13C{1H} NMR (100 MHz, DMSO-d6) δ 194.7, 189.2,
179.2, 140.7, 139.0, 132.1, 131.9, 131.3, 130.7, 130.2, 129.1, 128.6,
128.5, 128.4, 127.8, 124.5, 121.7, 105.0, 87.7. HRMS (ESI-TOF): m/
+
88.6. HRMS (ESI-TOF): m/z [M + H]+ calcd for C27H20NO3 :
+
z [M + H]+ calcd for C23H17BrNO3 : 434.0386; found: 434.0376.
406.1438; found: 406.1440.
4-Benzoyl-2-(2-bromophenyl)-2-hydroxy-5-phenyl-1,2-dihydro-
4-Benzoyl-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-hydroxy-5-
3H-pyrrol-3-one (3q). Yield 81%; 351.8 mg; white solid; mp 248−
1
phenyl-1,2-dihydro-3H-pyrrol-3-one (3y). Yield 82%; 339.0 mg;
250 °C. H NMR (400 MHz, DMSO-d6) δ 10.24 (d, J = 10.0 Hz,
1
white soild; mp 108−110 °C. H NMR (400 MHz, DMSO-d6) δ
1H), 8.11−8.07 (m, 1H), 7.80−7.71 (m, 3H), 7.64 (d, J = 7.6 Hz,
1H), 7.55−7.43 (m, 7H), 7.40−7.32 (m, 3H). 13C{1H} NMR (100
MHz, DMSO-d6) δ 194.8, 188.9, 179.6, 139.4, 137.4, 133.7, 131.7,
131.6, 130.9, 130.6, 130.5, 129.3, 128.4, 128.3, 127.6, 127.3, 120.4,
108.1, 86.5. HRMS (ESI-TOF): m/z [M + H]+ calcd for
10.37 (s, 1H), 7.61−7.54 (m, 5H), 7.48−7.45 (m, 3H), 7.38−7.34
(m, 3H), 6.99−6.94 (m, 2H), 6.88 (d, J = 8.8 Hz, 1H), 4.24 (s, 4H).
13C{1H} NMR (100 MHz, DMSO-d6) δ 195.2, 189.2, 178.7, 143.5,
143.1, 139.2, 131.9, 131.8, 131.1, 130.3, 129.1, 128.6, 128.4, 127.7,
118.2, 116.9, 114.6, 104.9, 88.1, 64.1, 55.0. HRMS (ESI-TOF): m/z
[M + Na]+ calcd for C25H19NO5Na+: 436.1155; found: 436.1157.
4-(4-Benzoyl-2-hydroxy-3-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-
2-yl)benzonitrile (3z). Yield 82%; 311.9 mg; yellow soild; mp 252−
254 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.55 (s, 1H), 7.91 (d, J =
8.4 Hz, 2H), 7.79 (s, 1H), 7.72 (d, J = 8.4 Hz, 2H), 7.64−7.56 (m,
5H), 7.50−7.46 (m, 3H), 7.38−7.34 (m, 2H). 13C{1H} NMR (100
MHz, DMSO-d6) δ 194.5, 189.2, 179.5, 143.3, 139.0, 132.5, 132.1,
132.0, 130.1, 129.1, 128.7, 128.4, 127.8, 126.6, 118.7, 111.2, 105.0,
+
C23H17BrNO3 : 434.0386; found: 434.0385.
4-Benzoyl-2-(3,4-dichlorophenyl)-2-hydroxy-5-phenyl-1,2-dihy-
dro-3H-pyrrol-3-one (3r). Yield 85%; 360.6 mg; white solid; mp 94−
96 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.50 (s, 1H), 7.78 (s, 1H),
7.74−7.69 (m, 2H), 7.65−7.61(m, 4H), 7.57 (d, J = 7.2 Hz, 1H),
7.50−7.47 (m, 4H), 7.38−7.35 (m, 2H). 13C{1H} NMR (100 MHz,
DMSO-d6) δ 194.4, 189.2, 179.4, 139.1, 139.0, 132.1, 132.0, 131.2,
130.8, 130.1, 129.1, 128.7, 128.4, 127.8, 125.9, 105.1, 87.4. HRMS
+
(ESI-TOF): m/z [M + H]+ calcd for C23H16Cl2NO3 : 424.0502;
+
88.0. HRMS (ESI-TOF): m/z [M + H]+ calcd for C24H17N2O3 :
found: 424.0509.
381.1234; found: 381.1240.
4-Benzoyl-2-(2,4-dichlorophenyl)-2-hydroxy-5-phenyl-1,2-dihy-
dro-3H-pyrrol-3-one (3s). Yield 80%; 339.4 mg; white solid; mp
150−152 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.55 (d, J = 4.8 Hz,
1H), 8.41−8.38 (m, 1H), 8.05−7.97 (m, 2H), 7.80−7.73 (m, 2H),
7.64−7.47 (m, 7H), 7.40−7.36 (m, 2H). 13C{1H} NMR (100 MHz,
DMSO-d6) δ 196.0, 189.3, 178.5, 139.3, 133.9, 133.8, 131.9, 130.5,
129.7, 129.2, 128.8, 128.6, 128.4, 127.8, 126.1, 125.7, 125.0, 105.8,
4-Benzoyl-2-hydroxy-2-(3-nitrophenyl)-5-phenyl-1,2-dihydro-
3H-pyrrol-3-one (4a). Yield 82%; 328.3 mg; white solid; mp 186−
188 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.59 (s, 1H), 8.40 (d, J =
1.6 Hz, 1H), 8.28−8.26 (m, 1H), 7.97−7.91 (m, 2H), 7.78−7.73 (m,
1H), 7.67−7.57 (m, 5H), 7.53−7.47 (m, 3H), 7.39−7.35 (m, 2H).
13C{1H} NMR (100 MHz, DMSO-d6) δ 194.5, 189.2, 179.5, 147.9,
+
88.4. HRMS (ESI-TOF): m/z [M + H]+ calcd for C23H16Cl2NO3 :
140.3, 139.0, 132.2, 132.0, 130.3, 130.1, 129.1, 128.7, 128.5, 127.8,
123.4, 120.6, 105.2, 87.6. HRMS (ESI-TOF): m/z [M + H]+ calcd for
424.0502; found: 424.0503.
+
C23H17N2O5 : 401.1132; found: 401.1130.
4-Benzoyl-2-hydroxy-5-phenyl-2-(4-(trifluoromethoxy)phenyl)-
1,2-dihydro-3H-pyrrol-3-one (3t). Yield 80%; 351.5 mg; white solid;
Methyl-4-(4-benzoyl-2-hydroxy-3-oxo-5-phenyl-2,3-dihydro-1H-
1
pyrrol-2-yl)benzoate (4b). Yield 84%; 347.3 mg; white solid; mp
mp 97−99 °C. H NMR (400 MHz, DMSO-d6) δ 10.60 (s, 1H),
1
114−116 °C. H NMR (400 MHz, DMSO-d6) δ 10.56 (s, 1H), 8.05
7.80−7.75 (m, 5H), 7.71 (d, J = 7.2 Hz, 2H), 7.58 (d, J = 7.2 Hz,
1H), 7.53−7.49 (m, 5H), 7.42−7.38 (m, 2H). 13C{1H} NMR (100
MHz, DMSO-d6) δ 195.1, 189.4, 179.3, 148.6, 139.3, 137.7, 132.1,
132.0, 130.4, 129.3, 128.8, 128.5, 127.9, 121.1, 120.3 (q, J = 255.0 Hz,
1JCF), 105.3, 88.1. 19F NMR (376 MHz, DMSO-d6) δ −56.80. HRMS
(d, J = 8.4 Hz, 2H), 7.71 (d, J = 6.8 Hz, 3H), 7.66−7.63 (m, 4H),
7.58 (s, 1H), 7.51−7.48 (m, 3H), 7.38−7.35 (m, 2H), 3.87 (s, 3H).
13C{1H} NMR (100 MHz, DMSO-d6) δ 194.8, 189.2, 179.3, 166.0,
143.2, 139.1, 132.1, 131.9, 130.2, 129.6, 129.4, 129.2, 128.7, 128.4,
E
J. Org. Chem. XXXX, XXX, XXX−XXX