Molecules 2018, 23, 252
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2H), 4.05 (q, J = 7.1 Hz, 2H), 2.57–2.65 (m, 2H), 2.24–2.31 (m, 2H), 2.03–2.12 (m, 1H), 1.83–1.91 (m, 1H),
1.09 (t, J = 7.0 Hz, 3H). 13C-NMR (DMSO-d6, 100 MHz)
: 171.64, 146.97, 146.25, 138.08, 132.98, 131.47,
δ
129.44, 129.33, 128.51, 125.15, 123.99, 123.47, 117.26, 109.30, 61.28, 54.07, 45.37, 31.76, 15.55, 13.72.
Methyl 2-((1-((4-cyano-1-naphthyl)methyl)-1H-imidazol-2-yl)thio)acetate (6q): White solid; 14.58 g (72%);
m.p. 116–118 ◦C. 1H-NMR (DMSO-d6, 400 MHz)
δ
: 8.32 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H),
8.13 (d, J = 7.6 Hz, 1H), 7.81–7.89 (m, 2H), 7.34 (s, 1H), 7.07 (d, J = 1.2 Hz, 1H), 6.81 (d, J = 7.6 Hz, 1H),
5.83 (s, 2H), 3.91 (s, 2H), 3.58 (s, 3H). 13C-NMR (DMSO-d6, 100 MHz)
: 169.09, 139.81, 139.44, 133.02,
δ
131.45, 129.58, 129.51, 129.18, 128.32, 125.04, 124.17, 123.08, 123.06, 117.40, 108.86, 52.26, 47.09, 35.26.
Ethyl 2-((1-((4-cyano-1-naphthyl)methyl)-1H-imidazol-2-yl)thio)-2-methylpropionate (6r): White solid; 17.76
◦
g (78%); m.p. 108–110 C. 1H-NMR (DMSO-d6, 400 MHz)
δ: 8.28 (d, J = 8.4 Hz, 1H), 8.18 (d, J = 8.0 Hz,
1H), 8.10 (d, J = 7.2 Hz, 1H), 7.81–7.89 (m, 2H), 7.46 (d, J = 1.2 Hz, 1H), 7.19 (d, J = 0.4 Hz, 1H), 6.67
(d, J = 7.6 Hz, 1H), 5.86 (s, 2H), 4.04 (q, J = 7.2 Hz, 2H), 1.46 (s, 6H), 1.11 (t, J = 7.0 Hz, 3H). 13C-NMR
(DMSO-d6, 100 MHz) δ: 172.56, 139.92, 137.14, 133.05, 131.38, 130.41, 129.38, 129.21, 128.35, 125.06,
124.11, 123.97, 122.69, 117.36, 108.80, 61.08, 52.84, 47.33, 25.62, 13.72.
Ethyl 1-((1-((4-cyano-1-naphthy◦l)methyl)-1H-imidazol-2-yl)thio)cyclobutanecarboxylate (6s): White solid;
1
17.85 g (76%); m.p. 135–137 C. H-NMR (DMSO-d6, 400 MHz)
δ: 8.28 (d, J = 8.4 Hz, 1H), 8.19
(d, J = 7.6 Hz, 1H), 8.10–8.12 (d, J = 7.6 Hz, 1H), 7.81–7.90 (m, 2H), 7.45 (s, 1H), 7.16 (s, 1H), 6.71 (d,
J = 7.6 Hz, 1H), 5.84 (s, 2H), 4.03 (q, J = 7.1 Hz, 2H), 2.53–2.56 (m, 2H), 2.23–2.29 (m, 2H), 1.98–2.07 (m,
1H), 1.76–1.84 (m, 1H), 1.09 (t, J = 7.2 Hz, 3H). 13C-NMR (DMSO-d6, 100 MHz)
δ: 172.24, 139.80, 137.62,
133.05, 131.40, 130.32, 129.41, 129.22, 128.37, 125.07, 123.95, 123.88, 122.79, 117.37, 108.83, 61.02, 54.17,
47.28, 31.33, 15.32, 13.75.
Methyl 2-((3-((4-cyano-1-naphthyl)methyl)pyridin-4-yl)thio)acetate (6t): Colorless oil; 15.05 g (72%).
1H-NMR (DMSO-d6, 400 MHz)
δ
: 8.37 (d, J = 5.2 Hz, 1H), 8.28 (d, J = 8.4 Hz, 1H), 8.17 (d, J = 8.4 Hz
1H), 8.12 (s, 1H), 8.07 (d, J = 7.2 Hz, 1H), 7.84 (t, J = 7.4 Hz, 1H), 7.76 (t, J = 7.6 Hz, 1H), 7.34 (d, J = 5.2 H,
1Hz), 7.15 (d, J = 7.6 Hz, 1H), 4.56 (s, 2H), 4.12 (s, 2H), 3.65 (s, 3H). 13C-NMR (DMSO-d6, 100 MHz)
,
δ:
168.93, 149.63, 147.96, 146.71, 141.46, 132.96, 131.69, 131.07, 130.96, 128.92, 128.07, 125.40, 125.05, 124.84,
119.59, 117.64, 107.90, 52.50, 33.09, 32.16.
Ethyl 2-((3-((4-cyano-1-naphthyl)methyl)pyridin-4-yl)thio)-2-methylpropionate (6u): Colorless oil; 15.93 g
(68%). 1H-NMR (DMSO-d6, 400 MHz)
δ: 8.45 (d, J = 5.2 Hz, 1H), 8.30 (s, 1H), 8.27 (d, J = 8.4 Hz,
1H), 8.17 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 7.6 Hz, 1H), 7.84 (t, J = 7.4 Hz, 1H), 7.78 (t, J = 7.2 Hz, 1H),
7.35 (d, J = 5.2 Hz, 1H), 7.05 (d, J = 3.6 Hz, 1H), 4.64 (s, 2H), 4.12 (q, J = 7.1 Hz, 2H), 1.51 (s, 6H), 1.13
(t, J = 7.2 Hz, 3H). 13C-NMR (DMSO-d6, 100 MHz)
δ: 172.82, 150.91, 147.99, 143.04, 142.39, 135.60,
132.96, 131.66, 130.93, 128.94, 128.06, 126.75, 125.55, 125.05, 124.81, 117.61, 107.83, 61.39, 50.98, 33.44,
25.84, 13.75.
Ethyl 1-((3-((4-cyano-1-naphthyl)methyl)pyridin-4-yl)thio)cyclobutanecarboxylate (6v): White solid; 17.87 g
(74%); m.p. 123–125 ◦C. 1H-NMR (DMSO-d6, 400 MHz)
1H), 8.17 (d, J = 8.0 Hz, 1H), 8.15 (s, 1H), 8.07 (d, J = 7.6 Hz, 1H), 7.84 (t, J = 7.6 Hz, 1H), 7.77 (t, J = 7.6 Hz
δ
: 8.36 (d, J = 5.2 Hz, 1H), 8.27 (d, J = 8.0 Hz
,
,
1H), 7.12 (d, J = 7.6 Hz, 1H), 7.06 (d, J = 5.6 Hz, 1H), 4.12 (q, J = 7.1 Hz, 2H), 2.79–2.86 (m, 2H), 2.20–2.27
(m, 2H), 2.06–2.17 (m, 1H), 1.90–2.00 (m, 1H), 1.09 (t, J = 7.2 Hz, 3H). 13C-NMR (DMSO-d6, 100 MHz)
δ:
172.31, 150.24, 147.90, 145.83, 141.56, 132.94, 131.68, 131.52, 131.04, 128.93, 128.04, 125.33, 125.06, 124.78,
120.76, 117.62, 107.94, 61.47, 50.89, 33.10, 31.74, 16.20, 13.77.
Ethyl 2-((1-((2-thiophenyl)methyl)-1H-imidazol-2-yl)thio)-2-methylpropionate (6w): Oil; 16.78 g (89%).
1H-NMR (DMSO-d6, 400 MHz)
δ: 7.44–7.46 (m, 2H), 7.05–7.06 (m, 2H), 6.96–6.98 (m, 1H), 5.40 (s,
2H), 4.03 (q, J = 7.2 Hz, 2H), 1.46 (s, 6H), 1.12 (t, J = 7.2 Hz, 3H). 13C-NMR (DMSO-d6, 100 MHz)
δ:
172.56, 139.55, 136.03, 130.07, 126.97, 126.73, 126.27, 123.13, 61.00, 52.80, 44.26, 25.56, 13.70.
Ethyl 1-((1-((2-thiophenyl)methyl)-1H-imidazol-2-yl)thio)cyclobutanecarboxylate (6x): Oil; 15.86 g (82%).
1H-NMR (DMSO-d6, 400 MHz)
: 7.46 (dd, J = 1.2 Hz and 5.2 Hz, 1H), 7.06 (d, J = 3.6 Hz, 1H), 7.03 (d,
δ