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Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry
Paper
2.49 (dd, J = 14.4, 8.1 Hz, 1H), 2.27 (s, 3H), 1.33 (s, 3H). 13C NMR 40.07, 34.97, 22.08, 15.87 ppm. HRMS (ESI) m/z calcd for
DOI: 10.1039/D0OB02103B
(126 MHz, CDCl3) δ 184.43,157.02, 148.19, 145.02, 137.18, 137.00, [C25H23N+H]+ 338.1903, found 338.1899.
133.62, 131.37, 128.52, 128.52, 128.49, 128.30, 127.93, 127.53, 3-Benzyl-2-methyl-3-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)-3H-
127.32, 126.18, 120.07, 113.28, 109.80, 70.60, 57.83, 40.29, 21.86, indole (3au). Total isolated yield: 65%, 47.3 mg, 0.13 mmol, 2E/2Z
15.82 ppm. HRMS (ESI) m/z calcd for [C28H27NO+H]+ 394.2171, >20:1. 3au, yellow oil; 1H NMR (500 MHz, CDCl3) δ 7.43 (d, J =
found 394.2180.
7.7 Hz, 1H), 7.32-7.27 (m, 5H), 7.22-7.17 (m, 3H), 7.12-7.08 (m,
5-Methyl-2,3-dimethyl-3-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)-
3H), 6.79 (dd, J = 7.8, 1.6 Hz, 2H), 6.50 (dd, J = 15.6, 10.3 Hz, 1H),
3H-indole (3ap). Total isolated yield: 98%, 59 mg, 0.2 mmol, 2E/2Z 6.38 (d, J = 15.7 Hz, 1H), 6.17 (dd, J = 15.0, 10.3 Hz, 1H), 5.08
=7.4:1. 3ap, yellow oil; 1H NMR (500 MHz, CDCl3) δ 7.44 (d, J = (ddd, J = 14.9, 8.2, 6.5 Hz, 1H), 3.29 (d, J = 13.6 Hz, 1H), 2.97 (d, J
7.8 Hz, 1H), 7.34-7.27 (m, 4H), 7.21-7.17 (m, 1H), 7.16-7.09 (m, = 13.6 Hz, 1H), 2.91 (dd, J = 15.0, 6.3 Hz, 1H), 2.70 (dd, J = 14.3,
2H), 6.55 (dd, J = 15.6, 10.4 Hz, 1H), 6.39 (d, J = 15.7 Hz, 1H), 6.15 8.5 Hz, 1H), 2.36 (s, 3H).13C NMR (126 MHz, CDCl3) δ 184.62,
(dd, J = 15.0, 10.4 Hz, 1H), 5.22-5.14 (m, 1H), 2.71 (dd, J = 14.8, 154.90, 140.75, 137.12, 135.66, 133.63, 131.36, 129.32, 128.49,
6.5 Hz, 1H), 2.49 (dd, J = 14.3, 8.3 Hz, 1H), 2.42 (s, 3H), 2.26 (s, 128.45, 127.90, 127.88, 127.76, 127.33, 126.68, 126.16, 124.68,
3H), 1.32 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 185.50, 152.13, 122.86, 119.82, 62.96, 42.07, 39.49, 16.89 ppm. HRMS (ESI) m/z
143.59, 137.24, 134.76, 133.46, 131.30, 128.62, 128.54, 128.38, calcd for [C27H25N+H]+ 364.2026, found 364.2057.
127.35, 126.41, 126.21, 123.72, 122.62, 119.45, 57.52, 40.33, 35.02, 4a-((2E,4E)-5-Phenylpenta-2,4-dien-1-yl)-2,3,4,4a-tetrahydro-
21.96, 21.52, 15.96 ppm. HRMS (ESI) m/z calcd for [C22H23N+H]+ 1H-carbazole (3av). Total isolated yield: 40%, 25.3 mg, 0.08 mmol,
302.1903, found 302.1906.
2,3,4-Trimethyl-3-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)-3H-
2E/2Z =7.3:1. 3av, yellow oil; 1H NMR (500 MHz, CDCl3) δ 7.63
(d, J = 7.7 Hz, 1H), 7.38-7.27 (m, 6H), 7.20 (dtd, J = 13.0, 7.3, 1.1
indole (3aq). Total isolated yield: 70%, 42.2 mg, 0.14 mmol, 2E/2Z Hz, 2H), 6.55 (dd, J = 15.6, 10.4 Hz, 1H), 6.38 (d, J = 15.7 Hz, 1H),
=5.4;1. 3aq, yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.38 (s, 1H), 6.14 (dd, J = 15.0, 10.4 Hz, 1H), 5.22 (dt, J = 15.0, 7.5 Hz, 1H),
7.29 (dt, J = 11.2, 5.5 Hz, 4H), 7.21-7.15 (m, 2H), 7.04 (d, J = 7.5 2.96-2.88 (m, 1H), 2.76 (dd, J = 14.3, 6.8 Hz, 1H), 2.59 (ddd, J =
Hz, 1H), 6.56 (dd, J = 15.7, 10.4 Hz, 1H), 6.39 (d, J = 15.7 Hz, 1H), 18.8, 13.3, 6.7 Hz, 2H), 2.44-2.37 (m, 1H), 2.26-2.19 (m, 1H), 1.85
6.15 (dd, J = 15.0, 10.4 Hz, 1H), 5.25-5.18 (m, 1H), 2.71 (dd, J = (qt, J = 13.6, 3.7 Hz, 1H), 1.77-1.67 (m, 1H), 1.45 (qt, J = 13.4, 4.2
14.2, 6.6 Hz, 1H), 2.47 (dd, J = 14.3, 8.3 Hz, 1H), 2.43 (s, 3H), 2.28 Hz, 1H), 1.18 (td, J = 13.5, 4.1 Hz, 1H). 13C NMR (126 MHz,
(s, 3H), 1.32 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 186.63, 154.42, CDCl3) δ 188.74, 154.79, 144.53, 137.15, 133.55, 131.20, 128.50,
140.35, 137.55, 137.14, 133.41, 131.23, 128.52, 128.49, 128.44, 128.46, 128.04, 127.63, 127.27, 126.12, 124.64, 121.87, 120.15,
127.25, 126.11, 125.67, 121.36, 120.55, 57.26, 40.20, 21.81, 21.45, 57.80, 36.75, 36.54, 30.11, 28.78, 21.05 ppm. HRMS (ESI) m/z
15.86 ppm. HRMS (ESI) m/z calcd for [C22H23N+H]+ 302.1909, calcd for [C23H23N+H]+ 314.1903, found 314.1905.
found 302.1901.
1,3-Dimethyl-1-((2E,4E)-5-phenylpenta-2,4-dien-1-
2,3,7-Trimethyl-3-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)-3H-
yl)naphthalen-2(1H)-one (5a). Total isolated yield: 97%, 61 mg,
indole (3ar) Total isolated yield: 91%, 54.8 mg, 0.18 mmol, 2E/2Z 0.19 mmol, 2E/2Z =5.0:1. 5a, yellow oil; 1H NMR (500 MHz,
>20:1. 3ar, yellow solid, m.p.112-114°C; 1H NMR (500 MHz, CDCl3) δ 7.43 (ddt, J = 24.4, 14.6, 7.8 Hz, 3H), 7.32-7.26 (m, 6H),
CDCl3) δ 7.31 (ddd, J = 15.2, 10.9, 4.7 Hz, 4H), 7.23-7.12 (m, 4H), 7.21-7.15 (m, 1H), 6.51 (dd, J = 15.6, 10.5 Hz, 1H), 6.34 (d, J = 15.7
6.57 (dd, J = 15.6, 10.4 Hz, 1H), 6.40 (d, J = 15.7 Hz, 1H), 6.16 (dd, Hz, 1H), 6.03 (dd, J = 14.5, 10.6 Hz, 1H), 5.28 (dt, J = 15.0, 7.4 Hz,
J = 15.0, 10.4 Hz, 1H), 5.26-5.19 (m, 1H), 2.73 (dd, J = 14.3, 6.4 1H), 2.91 (dd, J = 13.5, 8.2 Hz, 1H), 2.64 (dd, J = 13.5, 6.9 Hz, 1H),
Hz, 1H), 2.62 (s, 3H), 2.50 (dd, J = 14.5, 8.0 Hz, 1H), 2.31 (d, J = 2.00 (s, 3H), 1.53-1.47 (m, 3H). 13C NMR (126 MHz, CDCl3) δ
4.5 Hz, 3H), 1.34 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 185.36, 203.79, 144.92, 141.57, 137.34, 133.39, 132.87, 132.54, 131.04,
152.67, 143.24, 137.21, 133.45, 131.25, 129.43, 129.13, 128.58, 131.00, 130.21, 129.35, 128.80, 128.77, 128.57, 128.48, 128.11,
128.57, 128.48, 127.29, 126.15, 124.90, 119.20, 57.73, 40.27, 21.95, 127.42, 127.21, 126.73, 126.58, 126.48, 126.39, 126.13, 124.13,
16.89, 15.86 ppm. HRMS (ESI) m/z calcd for [C22H23N+H]+ 51.60, 46.29, 41.53, 26.53, 26.31, 15.87 ppm. HRMS (ESI) m/z
302.1903, found 302.1902.
calcd for [C23H23O+H]+ 315.1743, found 315.1745.
2,3,4,6-Tetramethyl-3-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)-3H- 1,3-Dimethyl-1-((2E,4E)-5-(3-fluorophenyl)penta-2,4-dien-1-
indole (3as). Total isolated yield: 90%, 56.7 mg, 0.18 mmol, 2E/2Z yl)naphthalen-2(1H)-one (5b). Total isolated yield: 94%, 62.5 mg,
=8.3;1. 3as, yellow solid, m.p.110-112°C; 1H NMR (500 MHz, 0.19 mmol, 2E/2Z =9.4:1. 5b, yellow oil; 1H NMR (500 MHz,
CDCl3) δ 7.30-7.24 (m, 4H), 7.22-7.16 (m, 2H), 6.80 (d, J = 9.5 Hz, CDCl3) δ 7.44-7.37 (m, 2H), 7.31-7.25 (m, 3H), 7.21 (td, J = 8.0, 6.1
1H), 6.48-6.42 (m, 1H), 6.35 (d, J = 15.7 Hz, 1H), 6.13 (dd, J = 15.1, Hz, 1H), 7.07-6.97 (m, 2H), 6.89-6.84 (m, 1H), 6.49 (dd, J = 15.6,
10.2 Hz, 1H), 4.99-4.92 (m, 1H), 3.04 (dd, J = 15.0, 6.4 Hz, 1H), 10.5 Hz, 1H), 6.29 (d, J = 15.6 Hz, 1H), 6.01 (dd, J = 15.1, 10.5 Hz,
2.63 (dd, J = 15.3, 8.1 Hz, 1H), 2.43 (s, 3H), 2.38 (s, 3H), 2.26 (s, 1H), 5.31 (dt, J = 15.1, 7.6 Hz, 1H), 2.93 (dd, J = 13.9, 8.5 Hz, 1H),
3H), 1.41 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 186.11, 154.91, 2.65 (dd, J = 13.2, 7.2 Hz, 1H), 2.00 (d, J = 1.3 Hz, 3H), 1.50 (s,
137.59, 137.21, 137.04, 132.59, 132.27, 131.09, 128.68, 128.60, 3H). 13C NMR (126 MHz, CDCl3) δ 203.72, 164.02, 162.08, 144.83,
128.45, 128.10, 127.24, 126.12, 118.44, 77.29, 77.03, 76.78, 58.42, 141.64, 139.75 (d, J = 7.7 Hz), 132.95, 132.51, 130.56, 130.29-
37.98, 21.29, 20.31, 17.77, 15.63 ppm. HRMS (ESI) m/z calcd for 129.64 (m), 128.85, 128.61, 126.78, 126.37, 122.09, 114.03, 113.86,
[C23H25N+H]+ 316.2060, found 316.2058.
2,3-Dimethyl-3-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)-3H-
112.43, 112.26, 51.53, 46.14, 26.71, 15.87 ppm. HRMS (ESI) m/z
calcd for [C23H21FO+H]+ 333.1655, found 333.1651.
benzo[g]indole (3at). Total isolated yield 55%, 37 mg, 0.11 mmol, 1,3-Dimethyl-1-((2E,4E)-5-(3-chlorophenyl)penta-2,4-dien-1-
2E/2Z =5.0;1. 3at, yellow oil. 1H NMR (500 MHz, CDCl3) δ 8.11- yl)naphthalen-2(1H)-one (5c). Total isolated yield: 91%, 63.5 mg,
7.94 (m, 2H), 7.91-7.79 (m, 2H), 7.59 (ddd, J = 9.5, 7.2, 1.1 Hz, 0.18 mmol, 2E/2Z =5.3:1. 5c, yellow oil; 1H NMR (500 MHz,
1H), 7.46 (ddd, J = 13.3, 8.0, 0.8 Hz, 1H), 7.32-7.22 (m, 4H), 7.19- CDCl3) δ 7.44-7.35 (m, 2H), 7.31-7.26 (m, 4H), 7.20-7.12 (m, 3H),
7.13 (m, 1H), 6.32 (dt, J = 31.5, 12.8 Hz, 2H), 6.05 (dd, J = 15.1, 9.9 6.49 (dd, J = 15.6, 10.5 Hz, 1H), 6.25 (d, J = 15.7 Hz, 1H), 6.00 (dd,
Hz, 1H), 4.85 (ddd, J = 14.8, 8.2, 6.4 Hz, 1H), 3.26 (dd, J = 15.3, 6.1 J = 15.0, 10.5 Hz, 1H), 5.31 (dt, J = 15.1, 7.6 Hz, 1H), 2.92 (dd, J =
Hz, 1H), 2.84 (dd, J = 14.8, 8.5 Hz, 1H), 2.40 (s, 3H), 1.59 (s, 3H). 13.7, 8.2 Hz, 1H), 2.65 (dd, J = 13.6, 6.9 Hz, 1H), 1.99 (d, J = 1.3
13C NMR (126 MHz, CDCl3) δ 187.92, 151.77, 137.16, 136.26, Hz, 3H), 1.50 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 203.68,
132.88, 132.31, 131.24, 129.74, 129.12, 128.85, 128.44 (d, J = 3.0 144.83, 141.62, 139.28, 134.44, 132.94, 132.53, 130.67, 130.19,
Hz), 128.17, 127.26, 126.39, 126.13, 124.40, 122.35, 119.89, 59.85, 130.15, 129.66, 129.44, 128.85, 128.61, 127.05, 126.79, 126.37,
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