Molecular Diversity
(C-1″), 11.6 (CH3). APCI-HRMS m/z: calcd for C13H14NO2
(MH+), 216.1019, found 216.1003; purity (HPLC): 99%
(254 nm). FTIR v/cm−1: 3175 (broad OH), 1626 (C=O),
1574 (C=C), 1234 (C–N).
(HPLC): 98% (254 nm). FTIR v/cm−1: 3079 (broad OH),
1626 (C=O), 1567 (C=C), 1223 (C–N).
1‑Cyclohexyl‑3‑hydroxy‑2‑methylpyridin‑4‑one (6) The title
compound was prepared from maltol and cyclohexylamine
in a yield of 6.86% (142 mg): mp 191.6–202.8 °C (metha-
nol), red solid. 1H NMR (600 MHz, DMSO-d6) δ 7.67 (br
s, 1H, H-6), 6.15 (br s, 1H, H-5), 4.02 (br s, 1H, H-1′), 2.32
3‑Hydroxy‑2‑methyl‑1‑(2‑phenylethyl)pyridin‑4‑one (3) The
title compound was prepared from maltol and 2-phenyl-
1-ethylamine in a yield of 6.42% (147 mg): mp 159.4–
160.8 °C (methanol), white crystals. H NMR (600 MHz,
(s, 3H, CH3), 2.09–0.74 (m, 10H, H-2′/6′, H-3′/5′, H-4′). 13
C
1
DMSO-d6) δ 7.45 (d, J = 7.3 Hz, 1H, H-6), 7.29 (br t,
J = 7.3 Hz, 2H, H3′/5′), 7.26–7.17 (m, 3H, H-2′/6′, H-4′),
6.06 (d, J=7.2 Hz, 1H, H-5), 4.14 (t, J=7.5 Hz, 2H, H-1″),
2.95 (t, J=7.5 Hz, 2H, H-2″), 2.25 (s, 3H, CH3). 13C NMR
(151 MHz, DMSO-d6) δ 168.9 (C-4), 145.4 (C-3), 137.52
(C-6), 137.46 (C-1′), 129.0 (C-2′/6′ or C-3′/5′), 128.7 (C-2),
128.5 (C-2′/6′ or C-3′/5′), 126.7 (C-4′), 110.6 (C-5), 53.9
(C-1″), 36.3 (C-2″), 11.3 (CH3). APCI-HRMS m/z: calcd
for C14H16NO2 (MH+), 230.1176, found 230.1186; purity
(HPLC): 99% (254 nm). FTIR v/cm−1: 3188 (broad OH),
1625 (C=O), 1558 (C=C), 1231 (C–N).
NMR (151 MHz, DMSO-d6) δ 168.6 (C-4), 145.3 (C-3),
133.3 (C-6), 128.8 (C-2), 110.8 (C-5), 59.0 (C-1′), 32.5
(C-2′/6′), 25.3 (C-3′/5′), 24.6 (C-4′), 11.3 (CH3). APCI-
HRMS m/z: calcd for C12H18NO2 (MH+), 208.1332, found
208.1344; purity (HPLC): 92% (254 nm). FTIR v/cm−1
:
3081 (broad OH), 1619 (C=O), 1566 (C=C), 1216 (C–N).
1‑Cyclopentyl‑3‑hydroxy‑2‑methylpyridin‑4‑one (7) The title
compound was prepared from maltol and cyclopentylamine
in a yield of 8.39% (162 mg): mp 51.4–51.5 °C (methanol),
red solid. 1H NMR (600 MHz, DMSO-d6) δ 7.62 (br s, 1H,
H-6), 6.17 (br s, 1H, H-5), 4.61 (br s, 1H, H-1′), 2.46–1.28
(m, 11H, H-2′/5′, H-3′/4′, CH3). 13C NMR (151 MHz,
DMSO-d6) δ 168.7 (C-4), 145.4 (C-3), 133.1 (C-6), 129.3
(C-2), 111.1 (C-5), 60.9 (C-1′), 32.5 (C-2′/5′), 23.7 (C-3′/4′),
11.7 (CH3). APCI-HRMS m/z: calcd for C11H16NO2 (MH+),
194.1176, found 194.1174; purity (HPLC): 91% (254 nm).
FTIR v/cm−1: 3078 (broad OH), 1621 (C=O), 1562 (C=C),
1212 (C–N).
3‑Hydroxy‑2‑methyl‑1‑(3‑phenylpropyl)pyridin‑4‑one (4) The
title compound was prepared from maltol and 3-phenyl-
1-propylamine in a yield of 12.92% (294 mg): mp 157.2–
1
159.3 °C (methanol), white crystals. H NMR (600 MHz,
DMSO-d6) δ 7.57 (d, J=7.3 Hz, 1H, H-6), 7.31–7.25 (m,
2H, H-3′/5′), 7.25–7.16 (m, 3H, H-2′/6′, H-4′), 6.13 (d,
J=7.2 Hz, 1H, H-5), 3.94 (t, J=7.4 Hz, 2H, H-1″), 2.60 (t,
J=7.8 Hz, 2H, H-3″), 2.23 (s, 3H, CH3), 1.94 (p, J=7.8 Hz,
2H, H-2″). 13C NMR (151 MHz, DMSO-d6) δ 168.9 (C-4),
145.5 (C-3), 140.8 (C-1′), 137.5 (C-6), 128.6 (C-2), 128.4
(C-2′/6′ or C-3′/5′), 128.2 (C-2′/6′ or C-3′/5′), 126.0 (C-4′),
110.7 (C-5), 52.4 (C-1″), 31.8 (C-2″, C-3″), 11.3 (CH3).
APCI-HRMS m/z: calcd for C15H18NO2 (MH+), 244.1332,
found 244.1331; purity (HPLC): 99% (254 nm). FTIR v/
cm−1: 3118 (broad OH), 1624 (C=O), 1572 (C=C), 1219
(C–N).
1‑(3‑Chlorophenyl)‑3‑hydroxy‑2‑methylpyridin‑4‑one (8) The
title compound was prepared from maltol and 3-chloro-
aniline in a yield of 5.06% (119 mg): mp 185.6–186.2 °C
1
(methanol), white solid. H NMR (600 MHz, DMSO-d6)
δ 7.68 (br t, J=2.0 Hz, 1H, H-2′), 7.64–7.55 (m, 3H, H-6′,
H-5′, H-6), 7.46 (ddd, J=7.7, 2.1, 1.2 Hz, 1H, H-4′), 6.23
(d, J = 7.3 Hz, 1H, H-5), 1.97 (s, 3H, CH3). 13C NMR
(151 MHz, DMSO-d6) δ 169.8 (C-4), 145.1 (C-3), 142.7
(C-1′), 137.9 (C-6), 133.8 (C-3′), 131.2 (C-6′), 129.4 (C-5′),
128.9 (C-2), 127.3 (C-2′), 126.2 (C-4′), 111.2 (C-5), 13.4
(CH3). APCI-HRMS m/z: calcd for C12H11ClNO2 (MH+),
236.0473, found 236.0446; purity (HPLC): 94% (254 nm).
FTIR v/cm−1: 3057 (broad OH), 1627 (C=O), 1561 (C=C),
1245 (C–N).
3‑Hydroxy‑2‑methyl‑1‑(4‑phenylbutyl)pyridin‑4‑one (5) The
title compound was prepared from maltol and 4-phenyl-
1-butylamine in a yield of 4.90% (126 mg): mp 171.6–
1
173.7 °C (methanol), white crystals. H NMR (600 MHz,
DMSO-d6) δ 7.55 (d, J=7.3 Hz, 1H, H-6), 7.30–7.24 (m,
2H, H-3′/5′), 7.21–7.14 (m, 3H, H-2′/H-6′, H-4′), 6.09 (d,
J=7.2 Hz, 1H, H-5), 3.94 (t, J=7.3 Hz, 2H, H-1″), 2.59 (t,
J=7.6 Hz, 2H, H-4″), 2.25 (s, 3H, CH3), 1.68–1.50 (m, 4H,
H-2″, H-3″). 13C NMR (151 MHz, DMSO-d6) δ 168.8 (C-4),
145.5 (C-3), 141.8 (C-1′), 137.6 (C-6), 128.5 (C-2), 128.32
(C-2′/6′ or C-3′/5′), 128.28 (C-2′/6′ or C-3′/5′), 125.8 (C-4′),
110.5 (C-5), 52.7 (C-1″), 34.6 (C-4″), 29.8 (C-2″ or C-3″),
27.7 (C-2″ or C-3″), 11.3 (CH3). APCI-HRMS m/z: calcd
for C16H20NO2 (MH+), 258.1489, found 258.1481; purity
1‑(4‑Chlorophenyl)‑3‑hydroxy‑2‑methylpyridin‑4‑one (9) The
title compound was prepared from maltol and 4-chloroani-
line in a yield of 5.09% (120 mg): mp 298.1–298.4 °C (meth-
1
anol), white solid. H NMR (600 MHz, DMSO-d6) δ 7.63
(d, J=8.7 Hz, 2H, H-2′/6′ or H-3′/5′), 7.55 (d, J =7.3 Hz,
1H, H-6), 7.51 (d, J=8.7 Hz, 2H, H-2′/6′ or H-3′/5′), 6.22
(d, J = 7.3 Hz, 1H, H-5), 1.96 (s, 3H, CH3). 13C NMR
(151 MHz, DMSO-d6) δ 169.8 (C-4), 145.1 (C-3), 140.4
(C-1′), 137.9 (C-6), 133.7 (C-4′), 129.7 (C-2′/6′ or C-3′/5′),
1 3