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4.5.1. (E)-4-(3-(2-Nitrovinyl)-1H-indol-1-yl)butanal (5). Yellow solid (95%); mp 81 °C; FTIR
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(KBr cm-1) 2733, 1718, 1554, 1379, 746; H NMR (300 MHz, CDCl3) δ: 9.74 (1H, s, -CHO),
8.21 (1H, d, J=13.2 Hz, ArCH=CH-), 7.70-7.74 (2H, m, ArH, -CHNO2), 7.52 (1H, s, ArH), 7.43
(1H, d, J=8.2 Hz, ArH), 7.27-7.37 (2H, m, ArH), 4.22 (2H, t, J=7.1Hz, -NCH2), 2.51 (2H, t,
J=6.8 Hz, -CH2CHO ), 2.21 (2H, quint, J=7.1 Hz, -CH2-); 13C NMR (75 MHz, CDCl3) δ: 200.2,
137.4, 135.4, 133.1, 132.1, 125.4, 123.9, 122.4, 120.7, 110.6, 108.3, 45.8, 40.2, 22.3; Found: C
65.19, H 5.87, N 10.94, C14H14N2O3 requires: C 65.11, H 5.42, N 10.85%.
4.5.2. (E)-Ethyl 3-(1-(4-oxobutyl)-1H-indol-3-yl)acrylate (9). White solid (96%); mp 61 °C;
FTIR (KBr cm-1) 2756, 1731, 1667, 1651, 1538, 1186; 1H NMR (300 MHz, CDCl3) δ: 9.73 (1H,
s, -CHO), 7.83-7.91 (2H, m, ArH, ArCH=CH-), 7.21-7.37 (4H, m, ArH), 6.40 (1H, d, J=15.6 Hz,
-CHCOOEt), 4.16-4.29 (4H, m, -NCH2, -CH2CH3), 2.46 (2H, t, J=6.8 Hz, -CH2CHO), 2.18 (2H,
quint, J=6.8 Hz, -CH2-), 1.35 (3H, t, J=7.1 Hz, -CH2CH3); 13C NMR (75 MHz, CDCl3) δ: 200.5,
168.1, 137.6, 137.1, 131.8, 125.9, 122.9, 121.2, 120.6, 112.7, 112.2, 109.9, 60.0, 45.3, 40.3, 22.3,
14.4; HRMS (ESI) (M+H) 286.1444; Calculated for C17H20NO3 286.1443.
4.5.3. (E)-3-(3-(2-Nitrovinyl)-1H-indol-1-yl)propanal (14). Yellow solid (94%); mp 112-115 °C;
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FTIR (KBr cm-1) 2727, 1714, 1612, 1526, 1389; H NMR (300 MHz, CDCl3) δ: 9.79 (1H, s, -
CHO), 8.19 (1H, d, J=13.3 Hz, ArCH=CH-), 7.65-7.75 (3H, m, ArH, -CHNO2), 7.29-7.42 (3H,
m, ArH), 4.51 (2H, t, J=6.2 Hz, -NCH2), 3.09 (2H, t, J=6.2 Hz, -CH2CHO ); 13C NMR (75 MHz,
CDCl3) δ: 198.6, 137.2, 136.5, 133.2, 132.1, 125.5, 123.9, 122.5, 120.8, 110.2, 108.3, 43.07,
39.5; HRMS (ESI) (M+H) 245.0930; Calculated for C13H13N2O3 245.0926.
4.5.4. (E)-Ethyl 3-(1-(3-oxopropyl)-1H-indol-3-yl)acrylate (17). Yellow oil (95%); FTIR (KBr
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cm-1) 2726, 1693, 1616, 1381, 1157; H NMR (300 MHz, CDCl3) δ: 9.80 (1H, s, -CHO), 7.81-
7.92 (2H, m, ArH, ArCH=CH-), 7.40 (1H, s, ArH), 7.23-7.34 (3H, m, ArH), 6.41 (1H, d, J=15.9
Hz, -CHCOOEt), 4.40 (2H, t, J=6.8 Hz, -NCH2), 4.24 (2H, q, J=7.1 Hz, -CH2CH3), 2.81 (2H, t,
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J=6.8 Hz, -CH2CHO), 1.33 (3H, t, J=7.1 Hz, -CH2CH3); C NMR (75 MHz, CDCl3) δ: 184.4,
172.3, 138.1, 137.1, 125.3, 124.0, 122.9, 122.1, 118.2, 109.9, 60.7, 46.1, 30.7, 24.9; HRMS
(ESI) (M+Na): 294.1104 Calculated for C16H17NO3Na 294.1106.
4.5.5. (E)-4-(3-Styryl-1H-indol-1-yl)butanal (20). Yellow oil (92%); FTIR (ATR cm-1) 2932,
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2724, 1714, 1627, 1456, 1360, 1165, 953, 737; H NMR (300 MHz, CDCl3) δ: 9.74 (1H, s, -
CHO), 8.01 (1H, d, J=7.6 Hz, ArH), 7.54 (2H, d, J=7.7 Hz, ArH), 7.10-7.46 (9H, m, ArH), 4.17
(2H, t, J=6.7 Hz, -NCH2), 2.43 (2H, t, J=6.7 Hz, -CH2CHO), 2.16 (2H, quint., J=6.7 Hz, -CH2-);
(signals of Z isomer were seen in very small proportion); 13C NMR (75 MHz, CDCl3) δ: 200.7,
138.5, 136.9, 128.5, 127.1, 126.5, 126.2, 125.7, 125.6, 125.1, 122.3, 121.3, 120.3, 120.1, 114.4,
109.6, 45.1, 40.5, 22.4; HRMS (ESI) (M+H): 290.1549; Calculated for C20H20NO 290.1545.
4.5.6. (Z)-4-(3-(Prop-1-en-1-yl)-1H-indol-1-yl)butanal (23). Viscous oil (95%); FTIR (ATR cm-
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1) 2928, 2873, 1716, 1611, 1466, 1366, 1169, 1075, 742; H NMR (300 MHz, CDCl3) δ: 9.82
(1H, s, -CHO), 7.69 (1H, d, J=7.7 Hz, ArH), 7.07-7.33 (4H, m, ArH), 6.67 (1H, d, J=11.5 Hz,