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Organic & Biomolecular Chemistry
Page 9 of 12
Journal Name
DOI: 10.1039/C7OB02498C
ARTICLE
CDCl3) δ = 8.19 (s, 1H), 8.12 (d, J = 8.4 Hz, 1H), 8.00 (d, J = 7.6 Hz, mp 68‐71 °C; 1H NMR (400 MHz, CDCl3) δ = 7.78 (d, J = 8.4 Hz, 2H),
2H), 7.92 (s, 1H), 7.76‐7.69 (m, 2H), 7.65 (d, J = 7.6 Hz, 2H), 7.50 (t, J 7.57 (d, J = 7.5 Hz, 1H), 7.49 (d, J = 7.6 Hz, 2H), 7.31‐7.27 (m, 5H),
= 7.6 Hz, 1H), 7.45 (t, J = 7.6 Hz, 2H), 7.37‐7.31 (m, 3H), 4.80‐4.76 7.22‐7.17 (m, 4H), 4.97‐4.94 (m, 1H), 3.67 (s, 3H), 3.56 (dd, J1 = 18.3,
(m, 1H), 4.70 (t, J = 8.0 Hz, 1H), 3.96‐3.78 (m, 2H), 2.45 (s, 3H), 1.08 J2 = 9.6 Hz, 1H), 3.17 (s, 3H), 3.14‐3.09 (m, 1H), 2.36 ppm (s, 3H); 13
C
(d, J = 6.1 Hz, 3H), 0.85 ppm (d, J = 6.1 Hz, 3H); 13C NMR (100 MHz, NMR (100 MHz, CDCl3) δ = 197.3, 170.3, 168.6, 144.4, 143.8, 140.5,
CDCl3) δ = 196.2, 166.3, 157.8, 148.9, 144.8, 134.7, 134.6, 134.1, 139.1, 136.2, 134.0, 129.1, 129.0,128.3, 128.0, 127.9, 127.8, 127.3,
133.5, 131.4, 131.1, 129.8, 129.6, 129.5, 129.2, 129.0, 128.6, 128.4, 125.9, 124.0,120.7, 67.8, 53.1, 52.2, 48.0, 42.6, 21.5 ppm; HRMS
128.2, 127.8, 126.6, 116.9, 71.6, 55.8, 46.2, 41.5, 21.7, 21.2, 20.7 (ESI) m/z calcd for C29H26O5 (M+H)+ 455.1858, found 455.1873.
ppm; HRMS (ESI) m/z calcd for C33H28N2O3 (M+H)+ 501.2178, found
501.2145.
(E)‐Ethyl‐2‐cyano‐3‐(4‐methylbenzylidene)‐1‐(2‐oxo‐2‐phenyle
(Z)‐Dimethyl1‐benzylidene‐3‐(2‐oxo‐2‐(thiophen‐2‐yl)ethyl)‐1,3‐
dihydro‐2H‐in dene‐2,2‐dicarboxylate (7d). Pale yellow solid; (200
mg, 93% yield); mp 60‐63 °C; H NMR (400 MHz, CDCl3) δ = 7.60‐
1
thyl)‐2,3‐dihydro‐1H‐cyclo‐penta[b]quinoline‐2‐carboxylate (6d). 7.56 (m, 3H), 7.49 (d, J = 8.4 Hz, 2H), 7.32‐7.25 (m, 5H), 7.23‐7.20
1
Colorless solid; (210 mg, 86 % yield); mp 132.1‐134.1 °C; H NMR (m, 2H), 7.06‐7.03 (m, 1H), 4.94‐4.91 (m, 1H), 3.65 (s, 3H), 3.49 (dd,
(400 MHz, CDCl3) δ = 8.16 (s, 1H), 8.13‐8.09 (m, 3H), 7.93 (s, 1H), J1 = 17.5, J2 = 8.4 Hz, 1H), 3.21 (s, 3H), 3.13 ppm (dd, J1 = 17.5, J2 =
7.77‐7.69 (m, 2H), 7.65‐7.62 (m, 1H), 7.55‐7.49 (m, 5H), 7.24 (d, J = 5.3 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ = 190.6, 170.1, 168.6,
8.0 Hz, 2H), 4.71 (t, J = 6.8 Hz, 1H), 4.00‐3.90 (m, 3H), 3.85‐3.79 (m, 144.1, 143.7, 140.5, 138.9, 136.2, 133.4, 131.9, 129.0, 128.5, 128.4,
1H), 2.39 (s, 3H), 1.04 ppm (t, J = 6.8 Hz, 3H); 13C NMR (100 MHz, 128.2, 128.0, 127.4, 126.0, 124.1, 120.8, 67.8, 53.1, 52.2, 47.9, 43.1
CDCl3) δ = 196.7, 167.0, 157.9, 149.0, 139.2, 136.0, 134.1, 133.9, ppm; HRMS (ESI) m/z calcd for C26H22O5S (M+H)+ 447.1266, found
133.8, 131.7, 131.5, 131.3, 129.9, 129.5, 129.2, 128.8, 128.3, 128.2, 447.1276.
127.8, 126.6, 116.8, 63.2, 55.6, 46.1, 41.7, 21.4, 13.4 ppm; HRMS
(E)‐Dimethyl‐3‐benzylidene‐1‐(2‐(4‐fluorophenyl)‐2‐oxoethyl)‐1‐
H‐cyclopenta[b]quinoline‐2,2(3H)‐dicarboxylate (7e). Colorless
(ESI) m/z calcd for C32H26N2O3(M+H)+ 487.2021, found 487.2004.
(E)‐Ethyl‐3‐benzylidene‐2‐cyano‐1‐(2‐oxo‐2‐(thiophen‐2‐yl)ethyl)‐ solid; (185 mg, 87% yield); mp 149‐151 °C; 1H NMR (400 MHz,
2,3‐dihydro‐1H‐cyclo‐penta[b]quinoline‐2‐carboxylate
(6e). CDCl3) δ = 8.16 (s, 1H), 8.10 (d, J = 9.1 Hz, 1H), 7.98‐7.95 (m, 2H),
1
Colorless solid; (211 mg, 88 % yield); mp 163‐166 °C; H NMR (400 7.91 (s, 1H), 7.73 (d, J = 8.4 Hz, 1H), 7.67 (t, J = 8.7 Hz, 1H), 7.61 (d, J
MHz, CDCl3) δ = 8.18 (s, 1H), 8.12 (d, J = 8.5 Hz, 1H), 7.96 (s, 1H), = 6.8 Hz, 2H), 7.47 (t, J = 8.4 Hz, 1H), 7.36 (t, J = 6.8 Hz, 2H), 7.31
7.88 (d, J = 8.4 Hz, 1H), 7.78‐7.76 (m, 1H), 7.73‐7.69 (m, 2H), 7.61‐ 7.29 (m, 1H), 7.10 (t, J = 8.4 Hz, 2H), 4.98 (t, J = 6.0 Hz, 1H), 3.65‐
7.59 (m, 2H), 7.53‐7.49 (m, 1H), 7.42 (t, J = 7.6 Hz, 2H), 7.37‐7.35 3.59 (m, 1H), 3.57 (s, 3H), 3.39 (s, 3H), 3.38‐3.32 ppm (m, 1H); 13C
(m, 1H), 7.19‐7.17 (m, 1H), 4.68 (t, J = 5.3 Hz, 1H), 3.92‐3.85 (m, 2H), NMR (100 MHz, CDCl3) δ = 195.8, 169.5, 168.4, 159.4, 148.6, 136.4,
3.83‐3.73 (m, 2H), 1.00 ppm (t, J = 7.6 Hz, 3H); 13C NMR (100 MHz, 135.9, 135.7, 132.8, 132.7, 131.1, 130.9, 130.7, 130.6, 129.4, 129.1,
CDCl3) δ = 189.3, 166.7, 157.5, 149.0, 143.0. 135.1, 134.7, 134.6, 128.3, 128.2, 128.0, 127.7, 126.2, 115.8, 115.6, 66.3, 53.0, 52.3,
133.6, 133.0,131.4, 131.3, 129.9, 129.3, 129.2, 128.9, 128.4, 128.2, 45.4, 41.9 ppm; HRMS (ESI) m/z calcd for C31H24FNO5 (M+H)+
127.8, 126.7, 116.7, 63.3, 55.5, 46.0, 41.7, 13.4 ppm; HRMS (ESI) 510.1716, found 510.1710.
m/z calcd for C29H22N2O3S (M+H)+ 479.1429, found 479.1401.
(E)‐Dimethyl‐3‐benzylidene‐1‐(2‐oxo‐2‐(p‐tolyl)ethyl)‐1H‐cyclop ‐
(Z)‐Dimethyl1‐benzylidene‐3‐(2‐oxo‐2‐phenylethyl)‐1H‐Inde ne‐ enta[b]quinoline‐2,2(3H)‐dicarboxylate (7f). Colorless solid; (196
1
2,2(3H)‐dicarbo xylate (7a). Pale Yellow solid; (189 mg, 86% yield); mg, 78% yield); mp 175.2‐178.1 °C. H NMR (400 MHz, CDCl3) δ =
1
mp 64‐67 °C; H NMR (400 MHz, CDCl3) δ = 7.87 (d, J = 8.2 Hz, 2H) 8.16 (s,1H), 8.10 (d, J = 8.4 Hz, 1H), 7.91 (s, 1H), 7.84 (d, J = 7.6 Hz,
7.57 (d, J = 7.6 Hz, 1H), 7.52‐7.47 (m, 3H), 7.38 (t, J = 7.4 Hz, 2H), 2H), 7.73 (d, J = 7.6 Hz, 1H), 7.67 (t, J = 6.8 Hz, 1H), 7.62 (d, J = 8.4
7.31‐7.25 (m, 5H), 7.23‐7.27 (m, 2H), 4.97‐4.94 (m, 1H). 3.67 (s, 3H), Hz, 2H), 7.46 (t, J = 6.8 Hz, 1H), 7.37 (t, J = 8.4 Hz, 2H), 7.31‐7.29 (m,
3.60 (dd, J1 = 19.3, J2 = 9.1 Hz, 1H), 3.18‐3.12 ppm (m, 4H); 13C NMR 1H), 7.23 (d, J = 8.4 Hz, 2H), 4.99 (t, J = 6.8 Hz, 1H), 3.63‐3.59 (m,
(100 MHz, CDCl3) δ = 197.7, 170.2, 168.6, 144.3, 140.5, 139.0, 136.5, 1H), 3.57 (s, 3H), 3.41‐3.34 (m, 1H), 3.39 (s, 3H), 2.39 ppm (s, 3H);
130.2, 129.0, 128.4, 128.3, 127.9, 125.9, 124.0, 120.8, 67.8, 53.4, 13C NMR (100 MHz, CDCl3) δ = 197.0, 169.5, 168.4, 159.5, 148.6,
52.2, 47.9, 42.7 ppm; HRMS (ESI) m/z calcd for C28H25O5 (M+H)+ 144.2, 136.4, 136.2, 135.7, 133.9, 131.0, 129.3, 129.2, 129.2, 129.1,
441.1702, found 441.1723.
128.4, 128.1, 128.0, 127.8, 126.1, 66.3, 52.9, 52.5, 45.4, 41.8, 21.6
(Z)‐Dimethyl1‐benzylidene‐3‐(2‐(4‐fluorophenyl)‐2‐oxoethy )‐1H‐ ppm; HRMS (ESI) m/z calcd for C32H28NO5 (M+H)+ 506.1967, found
indene‐2,2(3H)‐dicarboxylate (7b). Pale Yellow solid; (186 mg, 81% 506.1973.
yield); mp 61‐63 °C; 1H NMR (400 MHz, CDCl3) δ = 7.92‐7.88 (m, 2H),
(Z)‐Diethyl‐1‐benzylidene‐5‐fluoro‐3‐(2‐oxo‐2‐phenylethyl)‐1,3‐
7.58 (d, J = 6.8 Hz, 1H), 7.49 (d, J = 7.6 Hz, 2H), 7.32‐7.28 (m, 4H), dihydro‐2H‐indene‐2,2‐dicarboxylate (7g). Yellow solid; (200mg,
1
7.24‐7.20 (m, 2H), 7.16‐7.13 (m, 1H), 7.05 (t, J = 8.0 Hz, 2H), 4.96‐ 87% yield); mp 78‐81 °C; H NMR (400 MHz, CDCl3) δ = 7.90 (d, J =
4.93 (m, 1H), 3.68 (s, 3H), 3.58 (dd, J1 = 19.0, J2 = 9.1 Hz, 1H), 3.16 (s, 9.6 Hz, 2H), 7.56‐7.51 (m, 4H), 7.41 (t, J = 7.6 Hz, 2H), 7.30 (t, J = 6.8
3H), 3.10 ppm (dd, J1 = 18.3, J2 = 3.8 Hz, 1H); 13C NMR (100 MHz, Hz, 2H), 7.24‐7.22 (m, 1H), 7.18 (s, 1H), 7.00‐6.98 (m, 2H), 4.92 (t, J
CDCl3) δ = 196.2, 170.2, 168.7, 165.7 (d, J = 266.0 Hz), 144.2, 140.5, = 6.8 Hz, 1H), 4.16‐4.07 (m, 2H), 3.71‐3.67 (m, 1H), 3.62‐3.55 (m,
139.0, 136.2, 132.9, 130.6, 130.5, 129.0, 128.3, 128.0, 127.4, 126.1, 2H), 3.20 (dd, J1 = 19.1, J2 = 6.0 Hz, 1H), 1.17 (t, J = 6.8 Hz, 3H), 0.88
124.0, 120.8, 115.5 (d, J = 21.9 Hz), 67.8, 53.2, 52.3, 48.0, 42.7 ppm; ppm (t, J = 6.8 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ = 197.2, 169.4,
HRMS (ESI) m/z calcd for C28H23FO5 (M+H)+ 459.1607, found 168.0, 163.3 (d, J = 245.9 Hz), 146.7 (d, J = 7.6 Hz), 137.6, 136.6,
459.1626.
136.3 (d, J = 13.3 Hz), 133.1, 128.6, 128.2, 128.0, 127.9, 127.9,
(Z)‐Dimethyl‐1‐benzylidene‐3‐(2‐oxo‐2‐(p‐tolyl)ethyl)‐1H‐indene‐ 127.3, 125.5, 122.0 (d, J = 34.3 Hz), 115.1 (d, J = 23.8 Hz), 111.2 (d, J
2,2(3H)‐dicarb oxylate (7c). Pale Yellow solid; (182 mg, 80% yield);
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