E
J. Tong et al.
Paper
Synthesis
organic phase was washed with brine (5 mL), and dried over anhy-
drous Na2SO4. After the removal of the solvent under reduced pres-
sure, the residue was subjected to chromatography on a silica gel
(200–300 mesh) column (petroleum ether–EtOAc, 3:1) to afford 3a.
13C NMR (100 MHz, DMSO-d6): δ = 21.19, 41.30, 118.89, 120.34,
122.07, 123.91, 125.30, 125.76, 127.58, 128.35, 128.45, 128.59,
128.77, 134.20, 136.34, 143.98, 152.64.
1,1′-[(2-Chlorophenyl)methylene]bis(naphthalen-2-ol) (3g)2
1,1′-(Phenylmethylene)bis(naphthalen-2-ol) (3a)2
Yield: 402 mg (98%); white solid; mp 133–135 °C.
White solid; yield: 328 mg (87%); mp 194–196 °C.
1H NMR (400 MHz, DMSO-d6): δ = 7.03–7.16 (m, 8 H, ArH and CH),
7.27 (t, J = 8.4 Hz, 2 H, ArH), 7.37 (d, J = 7.6 Hz, 1 H, ArH), 7.63 (d, J =
8.4 Hz, 1 H, ArH), 7.71 (m, 3 H, ArH), 7.95 (d, J = 7.6 Hz, 1 H, ArH), 8.31
(s, 1 H, ArH), 9.59 (s, 1 H, OH), 10.10 (s, 1 H, OH).
1H NMR (400 MHz, DMSO-d6): δ = 7.02 (d, J = 7.2 Hz, 2 H, ArH), 7.06
(s, 1 H, CH), 7.11–7.23 (m, 9 H, ArH), 7.69 (d, J = 8.8 Hz, 2 H, ArH), 7.73
(d, J = 7.6 Hz, 2 H, ArH), 8.12 (d, J = 8.0 Hz, 2 H, ArH), 9.70 (s, 2 H, OH).
13C NMR (100 MHz, DMSO-d6): δ = 41.83, 119.36, 120.76, 122.55,
124.44, 125.40, 126.22, 128.11, 128.63, 128.83, 128.96, 129.09,
134.68, 144.52, 153.11.
13C NMR (100 MHz, DMSO-d6): δ = 40.00, 118.24, 118.39, 118.88,
120.79, 121.96, 122.10, 122.89, 124.43, 125.60, 126.01, 126.20,
126.76, 128.31, 128.39, 128.45, 128.63, 128.70, 130.57, 133.43,
133.98, 134.13, 142.23, 152.14, 153.07.
1,1′-(p-Tolylmethylene)bis(naphthalen-2-ol) (3b)2
1,1′-[(2,4-Dichlorophenyl)methylene]bis(naphthalen-2-ol) (3h)2
Yield: 324 mg (83%); white solid; mp 164–165 °C.
Yield: 404 mg (91%); white solid; mp 153–155 °C.
1H NMR (400 MHz, DMSO-d6): δ = 2.23 (s, 3 H, CH3), 6.91 (d, J = 7.6 Hz,
2 H, ArH), 6.98 (d, J = 7.6 Hz, 2 H, ArH), 7.02 (s, 1 H, CH), 7.13–7.23 (m,
6 H, ArH), 7.68 (d, J = 8.8 Hz, 2 H, ArH), 7.72 (d, J = 7.6 Hz, 2 H, ArH),
8.12 (d, J = 8.4 Hz, 2 H, ArH), 9.64 (s, 2 H, OH).
13C NMR (100 MHz, DMSO-d6): δ = 21.08, 41.54, 119.42, 120.90,
122.56, 124.42, 126.25, 128.56, 128.82, 128.85, 128.93, 129.12,
134.26, 134.70, 141.35, 153.16.
1H NMR (400 MHz, DMSO-d6): δ = 6.95 (d, J = 8.4 Hz, 1 H, ArH), 7.01
(s, 1 H, CH), 7.02 (d, J = 8.4 Hz, 1 H, ArH), 7.12–7.19 (m, 4 H, ArH),
7.22–7.28 (m, 2 H, ArH), 7.49 (d, J = 2.0 Hz, 1 H, ArH), 7.66–7.73 (m,
3 H, ArH), 7.88 (d, J = 8.8 Hz, 1 H, ArH), 8.25 (s, 1 H, ArH), 9.67 (s, 1 H,
OH), 10.18 (s, 1 H, OH).
13C NMR (100 MHz, DMSO-d6): δ = 39.60, 117.75, 118.17, 118.84,
120.32, 122.06, 122.17, 122.67, 124.27, 125.70, 126.17, 126.36,
127.71, 128.43, 128.49, 128.62, 128.93, 130.30, 131.71, 133.85,
133.93, 134.18, 141.69, 152.13, 152.98.
1,1′-[(4-Chlorophenyl)methylene]bis(naphthalen-2-ol) (3c)2
Yield: 349 mg (85%); white solid; mp 191–193 °C.
1H NMR (400 MHz, CDCl3): δ = 7.00–7.02 (m, 3 H, CH and ArH), 7.15–
7.23 (m, 8 H), 7.68 (d, J = 8.8 Hz, 2 H, ArH), 7.72 (d, J = 8.0 Hz, 2 H,
ArH), 8.12 (d, J = 8.4 Hz, 2 H, ArH), 9.84 (s, 2 H, OH).
13C NMR (100 MHz, CDCl3): δ = 41.37, 119.37, 120.39, 122.64, 124.30,
126.36, 127.93, 128.88, 129.09, 129.16, 129.84, 130.48, 134.56,
143.92, 153.02.
1,1′-(Naphthalen-2-ylmethylene)bis(naphthalen-2-ol) (3i)6e
Yield: 324 mg (76%); white solid; mp 126–129 °C.
1H NMR (400 MHz, CDCl3): δ = 7.25–7.33 (m, 7 H, CH and ArH), 7.39–
7.48 (m, 4 H, ArH), 7.63 (d, J = 8.0 Hz, 1 H, ArH), 7.80–7.84 (m, 5 H,
ArH), 7.89 (d, J = 8.0 Hz, 1 H, ArH), 8.30 (d, J = 8.4 Hz, 2 H, ArH), 9.87
(s, 2 H, OH).
13C NMR (100 MHz, CDCl3): δ = 41.94, 119.16, 120.33, 122.36, 124.12,
125.06, 125.18, 125.77, 126.07, 127.02, 127.40, 127.49, 128.39,
128.62, 128.87, 131.63, 133.23, 134.46, 142.38, 152.96.
1,1′-[(4-Nitrophenyl)methylene]bis(naphthalen-2-ol) (3d)6g
Yield: 413 mg (98%); yellow solid; mp 141–143 °C.
1H NMR (400 MHz, DMSO-d6): δ = 7.17–7.24 (m, 7 H, ArH and CH),
7.29 (d, J = 8.8 Hz, 2 H, ArH), 7.73 (d, J = 8.8 Hz, 4 H, ArH), 8.10 (d, J =
8.8 Hz, 2 H, ArH), 8.18 (d, J = 8.4 Hz, 2 H, ArH), 10.06 (s, 2 H, OH).
13C NMR (100 MHz, DMSO-d6): δ = 41.62, 118.85, 119.23, 122.32,
122.83, 123.65, 126.09, 126.55, 128.48, 128.67, 129.04, 129.26,
134.00, 145.11, 152.54.
1,1′-(Phenylmethylene)bis(6-bromonaphthalen-2-ol) (3j)
Yield: 431 mg (81%); white solid; mp 212–215 °C.
1H NMR (400 MHz, DMSO-d6): δ = 6.98–7.01 (m, 3 H, ArH and CH),
7.13–7.19 (m, 5 H, ArH), 7.29 (d, J = 8.8 Hz, 2 H, ArH), 7.69 (d, J =
8.8 Hz, 2 H, ArH), 7.97 (d, J = 8.8 Hz, 2 H, ArH), 7.99 (s, 2 H, ArH), 9.93
(s, 2 H, OH).
13C NMR (100 MHz, DMSO-d6): δ = 41.19, 114.92, 119.88, 120.51,
125.19, 126.68, 127.83, 128.12, 128.18, 129.93, 132.76, 143.47,
153.31.
1,1′-[(4-Bromophenyl)methylene]bis(naphthalen-2-ol) (3e)30
Yield: 359 mg (79%); yellow solid; mp 191–192 °C.
1H NMR (400 MHz, DMSO-d6): δ = 6.99 (d, J = 8.4 Hz, 2 H, ArH), 7.03
(s, 1 H, CH), 7.18–7.26 (m, 6 H, ArH), 7.38 (d, J = 8.4 Hz, 2 H, ArH), 7.72
(t, J = 8.8 Hz, 4 H, ArH), 8.15 (d, J = 8.4 Hz, 2 H, ArH), 9.92 (s, 2 H, OH).
13C NMR (100 MHz, DMSO-d6): δ = 40.94, 117.80, 118.91, 119.82,
122.16, 123.79, 125.89, 128.40, 128.59, 128.69, 130.36, 130.44,
134.08, 143.93, 152.58.
HRMS: m/z [M + H]+ calcd for C27H19Br2O2+: 532.9752; found:
532.9749.
1,1′-[(4-Nitrophenyl)methylene]bis(6-bromonaphthalen-2-ol)
(3k)6g
Yield: 531 mg (92%); yellow solid; mp 145–148 °C.
1,1′-(m-tolylmethylene)bis(naphthalen-2-ol) (3f)31
1H NMR (400 MHz, DMSO-d6): δ = 7.07 (s, 1 H, CH), 7.23 (d, J = 8.4 Hz,
2 H, ArH), 7.24 (d, J = 8.4 Hz, 2 H, ArH), 7.31 (d, J = 2.0 Hz, 1 H, ArH),
7.33 (d, J = 2.0 Hz, 1 H, ArH), 7.34 (d, J = 8.8 Hz, 2 H, ArH), 7.98–8.02
(m, 4 H, ArH), 8.10 (d, J = 8.4 Hz, 2 H, ArH), 10.25 (s, 2 H, OH).
Yield: 367 mg (94%); white solid; mp 123–125 °C.
1H NMR (400 MHz, DMSO-d6): δ = 2.16 (s, 3 H, CH3), 6.78 (d, J = 7.6 Hz,
1 H, ArH), 6.88 (s, 1 H, ArH), 6.93 (d, J = 7.2 Hz, 1 H, ArH), 7.02 (s, 1 H,
CH), 7.06 (d, J = 7.6 Hz, 1 H, ArH), 7.12–7.23 (m, 6 H, ArH), 7.69–7.73
(m, 4 H, ArH), 8.11 (d, J = 8.0 Hz, 2 H, ArH), 9.67 (s, 2 H, OH).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–H