Molecules 2018, 23, 2030
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2-(Dimethylamino)ethyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6a). Yield: 43%; yellow
oil; 1H-NMR (CDCl3)
11.76 (bs, 1H), 8.36 (d, J = 8.4 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 7.61 (t, J = 7.2 Hz,
1H), 7.51 (t, J = 7.2 Hz, 1H), 7.10 (d, J = 10.0 Hz, 1H), 5.67 (d, J = 10.0 Hz, 1H), 4.54 (d, J = 6.0 Hz, 2H),
2.76 (d, J = 6.0 Hz, 2H), 2.35 (s, 6H), 1.48 (s, 6H); 13C-NMR (CDCl3)
170.42, 154.37, 141.43, 128.99,
δ
δ
128.89, 128.68, 126.12, 125.27, 123.98, 122.00, 121.84, 112.84, 103.81, 74.84, 62.66, 57.17, 45.43, 26.96; MS
(ESI, m/z): calcd for C20H24NO4 [M + H]+ 342, found 342.
3-(Dimethylamino)propyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6b): Yield: 31%;
yellow gel; 1H-NMR (CDCl3)
δ 12.18 (bs, 1H), 8.36 (dd, J = 8.3, 0.4 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H),
7.62–7.59 (m, 1H), 7.52–7.48 (m, 1H), 7.13 (d, J = 10.0 Hz, 1H), 5.66 (d, J = 10.0 Hz, 1H), 4.49 (dd,
J = 6.4 Hz, 2H), 2.47 (dd, J = 7.1 Hz, 2H), 2.28 (s, 6H), 2.04–1.97 (m, 2H), 1.49 (s, 6H); MS (ESI, m/z)
calcd for C21H26NO4 [M + H]+ 356, found 356.
2-(Pyrrolidin-1-yl)ethyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6c): Yield: 9%; brown
oil; 1H-NMR (CDCl3)
δ 11.81 (bs, 1H), 8.35 (d, J = 8.3 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.60–7.56 (m, 1H),
7.52–7.47 (m, 1H), 7.09 (d, J = 10.0 Hz, 1H), 5.66 (d, J = 10.0 Hz, 1H), 4.57 (t, J = 5.9 Hz, 2H), 2.91
(t, J = 5.9 Hz, 2H), 2.66–7.64 (m, 4H), 1.85–1.82 (m, 4H), 1.49 (s, 6H); MS (ESI, m/z) calcd for C22H26NO4
[M + H]+ 368, found 368.
2-Morpholinoethyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6d): Yield: 30%; yellow gel;
1H-NMR (CDCl3)
δ
11.61 (s, 1H), 8.36 (d, J = 8.0 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 7.62–7.58 (m, 1H),
7.52–7.48 (m, 1H), 7.18 (d, J = 10.0 Hz, 1H), 5.66 (d, J = 10.0 Hz, 1H), 4.55 (t, J = 5.6 Hz, 2H), 3.76
(t, J = 4.6 Hz, 4H), 2.80 (t, J = 5.7 Hz, 2H), 2.59 (t, J = 4.3 Hz, 4H), 1.49 (s, 6H); 13C-NMR (DMSO-d6)
δ
168.3, 149.8, 140.8, 129.9, 128.7, 127.1, 126.5, 124.9, 123.4, 121.4, 121.1, 112.4, 107.2, 75.1, 63.1, 59.9, 54.2,
51.5, 26.5; MS (ESI, m/z) calcd for C22H26NO5 [M + H]+ 384, found 384.
3-Morpholinopropyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6e): Yield: 23%; yellow
1
gel; H-NMR (CDCl3)
δ 11.99 (bs, 1H), 8.36 (d, J = 8.3 Hz, 1H), 8.18 (d, J = 8.3 Hz, 1H), 7.65–7.61
(m, 1H), 7.55–7.51 (m, 1H), 6.99 (d, J = 10.0 Hz, 1H), 5.69 (d, J = 10.0 Hz, 1H), 4.53 (t, J = 6.1 Hz, 2H),
3.99 (t, J = 4.7 Hz, 4H), 3.17–3.13 (m, 4H), 2.37–2.30 (m, 2H), 1.85–1.60 (m, 2H), 1.50 (s, 6H); MS (ESI,
m/z) calcd for C23H28NO5 [M + H]+ 398, found 398.
(R)-(1-Methylpyrrolidin-2-yl)methyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6f): Yield:
1
16%; yellow oil; H-NMR (CDCl3)
δ 11.92 (s, 1H), 8.35 (d, J = 8.3 Hz, 1H), 8.16 (d, J = 8.3 Hz, 1H),
7.62–7.57 (m, 1H), 7.51–7.47 (m, 1H), 7.17 (d, J = 10.0 Hz, 1H), 5.67 (d, J = 10.0 Hz, 1H), 5.28–5.24
(m, 1H), 3.67 (d, J = 6.0 Hz, 2H), 2.80 (m, 1H), 2.51 (m, 2H), 2.37–2.32 (m, 4H), 2.00–1.90 (m, 3H), 1.50
(s, 6H); MS (ESI, m/z) calcd for C22H26NO4 [M + H]+ 368, found 368.
1-Methylpiperidin-4-yl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6g): Yield: 17%; pale
green oil; 1H-NMR (CDCl3)
δ 11.97 (s, 1H), 8.36 (d, J = 8.2 Hz, 1H), 8.17 (d, J = 8.3 Hz, 1H), 7.63–7.59
(m, 1H), 7.53–7.49 (m, 1H), 7.23 (d, J = 10.0 Hz, 1H), 5.66 (d, J = 10.0 Hz, 1H), 4.59 (m, 2H), 3.89 (m, 2H),
3.72 (m, 2H), 3.59 (m, 2H), 3.41 (s, 3H), 3.38 (m, 1H), 1.49 (s, 6H); MS (ESI, m/z) calcd for C22H26NO4
[M + H]+ 368, found 368.
2-(4-Methylpiperazin-1-yl)ethyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6h): Yield: 34%;
1
brown oil; H-NMR (MeOD)
δ 8.36 (d, J = 8.2 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 7.62–7.58 (m, 1H),
7.52–7.48 (m, 1H), 7.16 (d, J = 10.0 Hz, 1H), 5.66 (d, J = 10.0 Hz, 1H), 4.55 (t, J = 5.6 Hz, 2H), 2.80
(t, J = 5.7 Hz, 2H), 2.63–2.47 (m, 8H), 2.31 (s, 3H), 1.49 (s, 6H); MS (ESI, m/z) calcd for C23H29N2O4
[M + H]+ 397, found 397.
3-(4-Methylpiperazin-1-yl)propyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate (6i): Yield:
1
13%; yellow gel; H-NMR (MeOD)
δ 8.34 (d, J = 8.3 Hz, 1H), 8.16 (d, J = 8.2 Hz, 1H), 7.66 (m, 1H),
7.56 (m, 1H), 7.14 (d, J = 10.0 Hz, 1H), 5.83 (d, J = 10.0 Hz, 1H), 4.61 (t, J = 6.2 Hz, 2H), 3.76 (m, 2H),
3.37 (s, 8H), 3.02 (s, 3H), 2.36 (m, 2H), 1.51 (s, 6H); MS (ESI, m/z) calcd for C24H31N2O4 [M + H]+ 411,
found 411.