The Journal of Organic Chemistry
Page 24 of 43
The Journal of Organic Chemistry
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166.1, 163.4, 160.4, 137.6, 132.8, 130.5, 128.8, 128.4, 128.4, 125.8, 125.3, 119.7, 118.3, 117.6,
105.1, 69.8, 52.7, 51.7, 21.7; HRMS (ESI-TOF) m/z: [M+H]+ Calcd. For C20H20NO6: 370.1285,
Found: 370.1298; IR (neat, cm-1): υ 2956, 1698, 1444, 1211, 1177, 1100, 750.
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1-benzyl 2,3-dimethyl pyrrolo[1,2-a]quinoline-1,2,3-tricarboxylate (4t). Brown solid; yield
150 mg (72%); mp: 130.2-132.6 oC; 1H NMR (400 MHz, CDCl3) δ 8.21 (d, J = 9.4 Hz, 1H), 8.07
(d, J = 8.4 Hz, 1H), 7.76 (dd, J = 7.7, 1.2 Hz, 1H), 7.59 (d, J = 9.4 Hz, 1H), 7.55 – 7.44 (m, 4H),
7.40 (m, 3H), 5.40 (s, 2H), 3.88 (s, 3H), 3.61 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 165.4, 162.8,
160.2, 137.5, 134.4, 132.3, 130.7, 128.6, 128.3, 128.2, 128.2, 128.1, 125.4, 124.9, 119.3, 117.1,
117.1, 104.8, 67.3, 52.0, 51.3; HRMS (ESI-TOF) m/z: [M+H]+ Calcd. For C24H20NO6: 418.1285,
Found: 418.1290; IR (neat, cm-1): υ 2956, 1701, 1146, 1258, 1217, 1054, 751.
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1-tert-butyl 2,3-dimethyl pyrrolo[1,2-a]quinoline-1,2,3-tricarboxylate (4u). Light yellow solid;
yield 143 mg (75%); mp: 151.1-152.6 oC; 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J = 9.4 Hz, 1H),
8.07 (d, J = 8.6 Hz, 1H), 7.76 (dd, J = 7.8, 1.2 Hz, 1H), 7.67 – 7.54 (m, 2H), 7.53 – 7.42 (m, 1H),
4.01 (s, 3H), 3.91 (s, 3H), 1.64 (s, 9H); 13C NMR (101 MHz, CDCl3) δ 165.7, 163.0, 159.6, 136.9,
132.3, 129.5, 128.3, 127.9, 127.7, 125.2, 124.8, 119.2, 118.9, 117.2, 104.5, 82.8, 52.2, 51.2, 27.5;
HRMS (ESI-TOF) m/z: [M+H]+ Calcd. For C21H22NO6: 384.1442, Found: 384.1438; IR (neat,
cm-1): υ 2947, 1703, 1449, 1185, 1147, 810, 743.
1-allyl 2,3-dimethyl pyrrolo[1,2-a]quinoline-1,2,3-tricarboxylate (4v). Light yellow solid; yield
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161 mg (88%); mp: 97.0-99.5 C; H NMR (400 MHz, CDCl3) δ 8.21 (dd, J = 9.3, 7.4 Hz, 1H),
8.09 (dd, J = 8.6, 4.9 Hz, 1H), 7.80 – 7.72 (m, 1H), 7.65 – 7.53 (m, 2H), 7.53 – 7.42 (m, 1H), 6.04
(ddt, J = 16.4, 10.4, 5.9 Hz, 1H), 5.46 (dd, J = 17.2, 1.4 Hz, 1H), 5.35 (dd, J = 10.4, 1.1 Hz, 1H),
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4.87 (dd, J = 5.9, 1.1 Hz, 2H), 3.97 (s, 3H), 3.91 (s, 3H); C NMR (101 MHz, CDCl3) δ 166.1,
163.3, 160.5, 137.9, 132.8, 131.4, 131.2, 128.8, 128.6, 125.8, 125.3, 119.7, 119.4, 117.6, 117.6,
105.3, 100.0, 66.5, 52.8, 51.8; HRMS (ESI-TOF) m/z: [M+H]+ Calcd. For C20H18NO6: 368.1129,
Found: 368.1135; IR (neat, cm-1): υ 2955, 1703, 1482, 1256, 1218, 1177, 750.
dimethyl 1-(dimethylcarbamoyl)pyrrolo[1,2-a]quinoline-2,3-dicarboxylate (4w). Brown solid;
yield 35 mg (20%); mp: 160.4-163.2 oC; 1H NMR (400 MHz, CDCl3) δ 8.08 (d, J = 9.5 Hz, 1H),
7.90 (d, J = 8.6 Hz, 1H), 7.76 (dd, J = 7.8, 1.4 Hz, 1H), 7.57 – 7.52 (m, 1H), 7.51 – 7.44 (m, 1H),
7.42 (d, J = 9.5 Hz, 1H), 3.92 (d, J = 4.1 Hz, 6H), 3.28 (s, 3H), 2.91 (s, 3H); 13C NMR (101 MHz,
CDCl3) δ 164.4, 163.8, 163.7, 133.9, 132.3, 128.9, 128.8, 125.2, 125.1, 124.6, 123.6, 119.3, 117.7,
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