Jiang et al.
7
1.10.3
|
N1-(4-((2-aminophenyl) amino)-4-oxobutyl)-
1 mmol) was dissolved in the NH2OK solution and stirred
at room temperature for 6 h. After removing MeOH under
vacuum, the residue was acidified with 1 N HCl to a pH 3 and
then extracted with EtOAc. The organic phase was washed
with brine for three times and dried over anhydrous sodium
sulfate over night. After evaporating the solvent, the crude
product was purified via flash chromatography to afford the
N4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-
yl) terephthalamide (17c)
White solid, 23% yield. mp: 124–126 °C. 1H-NMR (600 MHz
DMSO-d6): δ 1.24–1.25 (m, 12H), 1.65 (s, 4H), 1.84–1.88
(m, 3H), 1.99 (s, 1H), 2.42 (t, J = 7.2 Hz, 2H), 4.88 (s, 2H),
6.54 (t, J = 7.2 Hz, 1H), 6.72 (d, J = 7.8 Hz, 1H), 6.90 (t,
J = 7.8 Hz, 1H), 7.16 (d, J = 7.2 Hz, 1H), 7.30 (d, J = 8.4 Hz,
1H), 7.60 (d, J = 7.8 Hz, 1H), 7.70 (s, 1H), 7.98–8.04 (m,
4H), 8.71 (s, 1H), 9.15 (s, 1H), 10.21 (s, 1H). 13C-NMR
(100 MHz DMSO-d ): δ 171.32, 166.03, 165.00, 145.02,
142.50, 140.48, 1376.59, 137.53, 136.93, 128.00, 127.65,
126.91, 126.22, 125.92, 123.93, 118.86, 118.65, 116.55,
116.27, 47.99, 35.07, 34.47, 34.03, 32.14, 25.81, 24.93.
HRMS (AP-ESI) m/z calculated for C32H38N4O3, [M + H]+
527.3017. Found, 527.3016.
1
compound 18a (0.16 g, yield: 38%). mp: 198–200 °C. H-
NMR (600 MHz DMSO-d6): δ 1.24–1.25 (m, 12H), 1.63–
1.67 (m, 4H), 3.81–3.82 (m, 2H), 7.30 (d, J = 8.4 Hz, 1H),
7.60 (d, J = 8.4 Hz, 1H), 7.68 (d, J = 1.8 Hz, 1H), 8.01 (d,
J = 8.4 Hz, 2H), 8.05 (d, J = 8.4 Hz, 2H), 8.84 (s, 1H), 8.93
(d, J = 5.4 Hz, 1H), 10.21 (s, 1H), 10.65 (s, 1H). 13C-NMR
(100 MHz DMSO-d ): δ 171.75, 166.27, 165.00, 145.02,
140.50, 137.92, 1366.92, 136.73, 128.13, 128.00, 127.84,
127.72, 126.92, 118.86, 118.67, 41.81, 35.12, 34.47, 34.03,
32.14. HRMS (AP-ESI) m/z calculated for C24H29N3O4,
[M + H]+ 424.2231. Found, 424.2232.
1.10.4
|
N1-(6-((2-aminophenyl) amino)-6-oxohexyl)-
N4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-
yl) terephthalamide (17d)
1.11.2
|
N1-(3-(hydroxyamino)-3-oxopropyl)-N4-
(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)
White solid, 19% yield. mp: 104–105°C. 1H-NMR
(600 MHz DMSO-d6): δ 1.24–1.25 (m, 12H), 1.37–1.39
(m, 2H), 1.57–1.62 (m, 2H), 1.65–1.66 (m, 6H), 2.34 (t,
J = 6.6 Hz, 2H), 3.31 (q, J = 6.6 Hz, 2H), 4.82 (s, 2H), 6.54
(td, J1 = 1.2 Hz, J2 = 8.4 Hz, 1H), 6.72 (dd, J1 = 1.2 Hz,
J2 = 8.4 Hz, 1H), 6.90 (td, J1 = 1.2 Hz, J2 = 8.4 Hz,
1H), 7.15 (dd, J1 = 1.2 Hz, J2 = 8.4 Hz, 1H), 7.30 (d,
J = 8.4 Hz, 1H), 7.59 (dd, J1 = 2.4 Hz, J2 = 9.0 Hz, 1H),
7.68 (d, J = 2.4 Hz, 1H), 7.97 (d, J = 8.4 Hz, 2H), 8.03
(d, J = 8.4 Hz, 2H), 8.65 (t, J = 6.0 Hz, 1H), 9.10 (s, 1H),
10.19 (s, 1H). 13C-NMR (100 MHz DMSO-d6): δ 171.58,
165.87, 165.03, 145.02, 142.33, 140.48, 137.61, 137.56,
136.93, 128.00, 127.59, 126.91, 126.14, 125.75, 124.09,
118.85, 118.64, 116.65, 116.37, 36.22, 35.08, 34.48,
34.04, 32.14, 29.39, 26.70, 25.57. HRMS (AP-ESI) m/z
calculated for C34H42N4O3, [M + H]+ 555.3333. Found,
555.3335.
terephthalamide (18b)
White solid, 26% yield. mp: 123–125 °C. 1H-NMR (600 MHz
DMSO-d ): δ 1.24–1.25 (m, 12H), 1.65–1.66 (m, 4H), 2.30 (t,
J = 7.2 H6z, 2H), 3.46–3.49 (m, 2H), 7.30 (d, J = 8.4 Hz, 1H),
7.59 (dd, J1 = 1.8 Hz, J2 = 8.4 Hz, 1H), 7.68 (d, J = 1.8 Hz,
1H), 7.96 (d, J = 8.4 Hz, 2H), 8.03 (d, J = 8.4 Hz, 2H), 8.73
(t, J = 6.0 Hz, 1H), 8.77 (d, J = 1.2 Hz, 1H), 10.20 (s, 1H),
10.48 (s, 1H). 13C-NMR (100 MHz DMSO-d6): δ 167.76,
165.99, 165.00, 145.03, 140.50, 137.67, 137.32, 136.91,
128.02, 127.61, 126.91, 118.85, 118.65, 36.61, 35.12, 34.47,
34.03, 32.84, 32.14. HRMS (AP-ESI) m/z calculated for
C25H31N3O4, [M + H]+ 438.2387. Found, 438.2386.
1.11.3
|
N1-(4-(hydroxyamino)-4-oxobutyl)-N4-
(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)
terephthalamide (18c)
White solid, 31% yield. mp: 205–207 °C. 1H-NMR (600 MHz
DMSO): δ 1.24–1.25 (m, 12H), 1.63–1.66 (m, 4H), 1.76–1.78
(m, 2H), 2.05 (t, J = 7.8 Hz, 2H), 3.29 (q, J = 6.6 Hz, 2H),
7.30 (d, J = 8.4 Hz, 1H), 7.60 (dd, J1 = 1.8 Hz, J2 = 8.4 Hz,
1H), 7.69 (d, J = 1.8 Hz, 1H), 7.98 (d, J = 8.4 Hz, 2H),
8.04 (d, J = 8.4 Hz, 2H), 8.70 (t, J = 6.0 Hz, 1H), 8.73 (d,
J = 1.8 Hz 1H), 10.22 (s, 1H), 10.43 (s, 1H). 13C-NMR
(100 MHz DMSO-d ): δ 169.38, 165.96, 165.01, 145.00,
140.45, 137.55, 1376.46, 136.95, 128.02, 127.65, 126.88,
118.88, 118.70, 39.48, 35.07, 34.47, 34.02, 32.14, 30.50,
25.72. HRMS (AP-ESI) m/z calculated for C26H33N3O4,
[M + H]+ 452.2544. Found, 452.2543.
1.11 | General procedure for the
preparation of 18a–c
1.11.1 | N1-(2-(hydroxyamino)-2-oxoethyl)-
N4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaph
thalen-2-yl) terephthalamide (18a)
KOH (28 g, 509 mmol) and NH2OH·HCl (23.35 g,
343 mmol) were dissolved, respectively, in 70 and 120 mL
of MeOH to get solution A and solution B. Next, solution A
was added dropwise to solution B. After filtering the precip-
itate (KCl), a NH2OK solution was obtained. 15a (0.42 g,