An Efcient One‑Pot Four‑Component Synthesis of 9‑Aryl‑Hexahydroacridine‑1,8‑Dione…
Calcd. for C23H27NO2: C 79.08, H 7.74, N 4.01%, found: C
79.12, H 7.79, N 3.98%.
6.91 (t, J = 8.0 Hz, 1H); 6.97 (t, J = 7.5 Hz, 2H); 7.08 (d,
J=7.5 Hz, 1H); 8.39 (s, 1H). 13C NMR (125 MHz, CDCl3)
δ (ppm): 19.34, 26.39, 28.92, 31.89, 40.05, 50.30, 113.92,
125.01, 127.58, 128.96, 129.02, 129.06, 135.56, 146.09,
148.14, 195.07. Anal. Calcd. for C24H29NO2: C 79.34, H
7.99, N 3.86%, found: C 79.37, H 8.04, N 3.81%.
9-(3-Bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4b yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.97 (s, 6H); 1.08 (s, 6H); 2.13-
2.38 (m, 8H); 5.02 (s, 1H); 7.05 (t, J = 8.0 Hz, 1H); 7.17
(d, J=8.0 Hz, 1H); 7.32 (d, J=6.0 Hz, 1H); 7.40 (s, 1H);
8.16 (s, 1H). 13C NMR (125 MHz, CDCl3) δ (ppm): 26.96,
29.29, 32.35, 39.91, 40.55, 50.54, 112.37, 121.74, 126.95,
128.59, 129.16, 130.66, 148.59, 195.00. Anal. Calcd. for
C23H26BrNO2: C 64.49, H 6.07, N 3.27%, found: C 64.52,
H 6.12, N 3.25%.
9-(3-Methylphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4h yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.95 (s, 6H); 1.06 (s, 6H);
2.10-2.32 (m, 11H); 5.01 (s, 1H); 6.85 (d, J = 7.0 Hz, 1H);
7.03-7.09 (m, 2H); 7.14 (s, 1H); 8.40 (s, 1H). 13C NMR
(125 MHz, CDCl3) δ (ppm): 21.56, 27.05, 29.57, 32.50,
40.57, 50.88, 112.98, 125.01, 126.55, 127.68, 128.92,
136.94, 146.78, 149.11, 149.17, 195.56. Anal. Calcd. for
C24H29NO2: C 79.34, H 7.99, N 3.86%, found: C 79.35, H
8.02, N 3.83%.
9-(4-Bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4c yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.95 (s, 6H); 1.07 (s, 6H); 2.12-
2.32 (m, 8H); 5.03 (s, 1H); 7.22 (d, J=8.5 Hz, 2H); 7.29 (d,
J=8.5 Hz, 2H); 8.45 (s, 1H). 13C NMR (125 MHz, CDCl3)
δ (ppm): 27.17, 29.65, 32.63, 40.67, 50.90, 112.70, 119.65,
129.99, 130.97, 145.99, 149.44, 195.79. Anal. Calcd. for
C23H26BrNO2: C 64.49, H 6.07, N 3.27%, found: C 64.54,
H 6.09, N 3.29%.
9-(4-Methylphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4i yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.95 (s, 6H); 1.05 (s, 6H);
2.12-2.28 (m, 11H); 5.06 (s, 1H); 6.99 (d, J = 8.0 Hz, 2H);
7.22 (d, J=8.0 Hz, 2H); 8.50 (s, 1H). 13C NMR (125 MHz,
CDCl3) δ (ppm): 21.09, 27.08, 29.55, 32.55, 40.51, 50.99,
113.09, 127.88, 128.67, 135.14, 143.86, 149.79, 196.13.
Anal. Calcd. for C24H29NO2: C 79.34, H 7.99, N 3.86%,
found: C 79.38, H 8.05, N 3.86%.
9-(2-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4d yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.95 (s, 6H); 1.07 (s, 6H); 2.02-
2.39 (m, 8H); 5.25 (s, 1H); 6.98 (t, J=8.0 Hz, 1H); 7.09 (t,
J=7.5 Hz, 1H); 7.18 (d, J=7.5 Hz, 1H); 7.39 (d, J=8.0 Hz,
1H); 8.84 (s, 1H). 13C NMR (125 MHz, CDCl3) δ (ppm):
26.86, 29.34, 32.08, 39.91, 40.31, 50.60, 111.60, 125.89,
126.64, 129.19, 131.91, 132.86, 143.82, 149.38, 194.87.
Anal. Calcd. for C23H26ClNO2: C 72.06, H 6.79, N 3.66%,
found: C 72.11, H 6.82, N 3.61%.
9-(2-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4k yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.90 (s, 6H); 1.04 (s, 6H);
2.02-2.33 (m, 8H); 3.78 (s, 3H); 5.16 (s, 1H); 6.75-6.80
(m, 2H); 7.03 (t, J = 7.5 Hz, 1H); 7.37 (d, J = 7.0 Hz,
1H); 8.62 (s, 1H). 13C NMR (125 MHz, CDCl3) δ (ppm):
26.44, 29.67, 32.28, 50.89, 55.19, 110.66, 111.37, 119.76,
126.86, 131.57, 133.94, 149.62, 157.63, 195.21. Anal.
Calcd. for C24H29NO3: C 75.99, H 7.65, N 3.69%, found:
C 76.03, H 7.68, N 3.64%.
9-(4-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4e yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.95 (s, 6H); 1.07 (s, 6H); 2.17-
2.29 (m, 8H); 5.07 (s, 1H); 7.16 (d, J=8.5 Hz, 2H); 7.29 (d,
J=8.5 Hz, 2H); 8.49 (s, 1H). 13C NMR (125 MHz, CDCl3)
δ (ppm): 27.17, 29.69, 32.72, 40.70, 50.98, 112.85, 128.19,
129.57, 131.65, 145.39, 149.79, 196.16. Anal. Calcd. for
C23H26ClNO2: C 72.06, H 6.79, N 3.66%, found: C 72.09,
H 6.80, N 3.63%.
9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4l yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.95 (s, 6H); 1.06 (s, 6H);
2.12-2.28 (m, 8H); 3.67 (s, 3H); 5.04 (s, 1H); 6.71 (d,
J = 8.5 Hz, 2H); 7.24 (d, J= 8.5 Hz, 2H); 7.92 (s, 1H). 13
C
9-(2-Fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
NMR (125 MHz, CDCl3) δ (ppm): 27.11, 29.57, 32.59,
40.66, 50.89, 55.01, 113.29, 113.39, 128.93, 139.18,
148.96, 157.64, 195.99. Anal. Calcd. for C24H29NO3: C
75.99, H 7.65, N 3.69%, found: C 76.05, H 7.71, N 3.65%.
9-(2-Nitrophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
hexahydroacridine-1,8-dione, 4f yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.94 (s, 6H); 1.05 (s, 6H);
2.10-2.30 (m, 8H); 5.24 (s, 1H); 6.89 (t, J = 9.5 Hz, 1H);
6.99-7.08 (m, 2H); 7.45 (t, J = 7.5 Hz, 1H); 8.01 (s, 1H).
13C NMR (125 MHz, CDCl3) δ (ppm): 26.91, 29.64, 32.59,
40.69, 50.92, 111.77, 115.20, 123.56, 127.64, 131.69,
133.04, 149.71, 195.81. Anal. Calcd. for C23H26FNO2: C
75.20, H 7.08, N 3.81%, found: C 75.25, H 7.11, N 3.75%.
9-(2-Methylphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8-dione, 4g yellow solid. 1H
NMR (500 MHz, CDCl3) δ (ppm): 0.92 (s, 6H); 1.06
(s, 6H); 2.05-2.37 (m, 8H); 2.84 (s, 3H); 5.06 (s, 1H);
1
hexahydroacridine-1,8-dione, 4m yellow solid. H NMR
(500 MHz, CDCl3) δ (ppm): 0.92 (s, 6H); 1.03 (s, 6H);
2.07–2.32 (m, 8H); 5.30 (s, 1H); 7.19 (t, J = 8.5 Hz, 1H);
7.45–7.50 (m, 2H); 7.71 (d, J = 8.0 Hz, 1H); 8.20 (s, 1H).
13C NMR (125 MHz, CDCl3) δ (ppm): 27.27, 29.17,
32.35, 40.55, 50.66, 112.15, 123.89, 126.31, 130.82,
130.84, 131.98, 141.27, 149.71, 195.17. Anal. Calcd. for
1 3