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analysis calcd (%) for C16H15O1N+0.5H2O: C 78.02, H 6.55, N 5.69;
Preparation of 1 f
found: C 78.11, H 6.67, N 5.68.
NaH (60% in oil, 630 mg, 15.5 mmol) was added to a mixture of 9-
(10H)-acridone (2.51 g, 12.9 mmol) in dry DMF (100 mL). The mix-
ture was stirred at RT for 20 min. 1-Iodohexane (2.70 mL,
18.3 mmol) was then added and the mixture was stirred at RT for
22.5 h. The mixture was diluted with an excess amount of water.
The resulting precipitate was collected by filtration, washed with
water, and then dried under vacuum to give 1 f (3.28 g, 91%) as
Preparation of 2c
A mixture of 1c (1.01 g, 4.26 mmol) and malononitrile (3.22 g,
48.7 mmol) in Ac2O (100 mL) was stirred at 1308C for 17.5 h. After
the mixture was allowed to cool to RT, the resulting crystalline pre-
cipitate was collected by filtration and washed with a small
amount of Ac2O to give 2c (963 mg, 79%) as an orange crystalline
solid. M.p. 253–2548C; 1H NMR (400 MHz): d=8.57 (dd, J=8.2,
1.4 Hz, 2H), 7.73 (ddd, J=8.6, 7.1, 1.5 Hz, 2H), 7.49 (brd, J=8.7 Hz,
2H), 7.35 (ddd, J=8.1, 7.1, 1.0 Hz, 2H), 4.32–4.25 (m, 2H), 2.08–1.97
(m, 2H), 1.17 ppm (t, J=7.4 Hz, 3H); 13C NMR (100 MHz): d=156.3,
138.8, 133.5, 127.1, 121.8, 118.0, 117.6, 114.2, 68.1, 49.6, 20.2,
11.2 ppm; IR: n˜ =2202, 2189, 1604, 1581, 1554, 1499, 1479, 1461,
1380, 1347, 1296, 1263, 1221, 1201, 1184, 1109, 1058, 1027, 950,
1
a yellow solid. M.p. 114–1158C; H NMR (400 MHz): d=8.54 (dd, J=
8.1, 1.7 Hz, 2H), 7.67 (ddd, J=8.8, 6.9, 1.8 Hz, 2H), 7.43 (d, J=
8.8 Hz, 2H), 7.24 (ddd, J=7.9, 7.0, 0.8 Hz, 2H), 4.27–4.20 (m, 2H),
1.92–1.82 (m, 2H), 1.57–1.47 (m, 2H), 1.45–1.30 (m, 4H), 0.93 ppm
(t, J=7.0 Hz, 3H); 13C NMR (100 MHz): d=177.8, 141.6, 133.7, 127.8,
122.3, 121.0, 114.5, 46.1, 31.4, 27.0, 26.5, 22.6, 13.9 ppm; IR: n˜ =
2954, 2928, 2868, 2854, 1635, 1608, 1594, 1492, 1459, 1377, 1339,
1286, 1263, 1221, 1190, 1175, 1098, 1046, 936, 896, 864, 799, 767,
752, 732, 684, 671, 644, 606, 569, 545 cmÀ1; HRMS (FAB): m/z calcd
for C19H22ON [M+H]+: 280.1701; found: 280.1700; elemental analy-
sis calcd (%) for C19H21ON: C 81.68, H 7.58, N 5.01; found: C 81.40,
H 7.74, N 4.82.
899, 851, 776, 751, 670, 660, 643, 627, 570, 557, 447, 427 cmÀ1
;
HRMS (FAB): m/z calcd for C19H16N3 [M+H]+: 286.1344; found:
286.1348; elemental analysis calcd (%) for C19H16N3: C 79.98, H 5.30,
N 14.78; found: C 79.44, H 5.45, N 14.54.
Preparation of 2 f
A mixture of 1 f (1.14 g, 4.08 mmol) and malononitrile (3.84 g,
58.1 mmol) in Ac2O (100 mL) was stirred at 1308C for 21 h. After
the solvent was evaporated under reduced pressure, the crude
product was recrystallized from Ac2O to give 2 f (816 mg, 61%) as
Preparation of 1e
NaH (60% in oil, 630 mg, 15.5 mmol) was added to a mixture of 9-
(10H)-acridone (2.52 g, 12.9 mmol) in dry DMF (100 mL). The mix-
ture was stirred at RT for 30 min. 1-Iodopentane (2.30 mL,
17.7 mmol) was then added and the mixture was stirred at RT for
22.5 h. The mixture was diluted with an excess amount of water.
The resulting precipitate was collected by filtration, washed with
water, and then dried under vacuum to give 1e (3.33 g, 97%) as
1
an orange solid. M.p. 139–1408C; H NMR (400 MHz): d=8.55 (dd,
J=8.2, 1.4 Hz, 2H), 7.71 (ddd, J=8.7, 7.2, 1.5 Hz, 2H), 7.47 (brd, J=
8.5 Hz, 2H), 7.33 (ddd, J=8.2, 7.2, 1.1 Hz, 2H), 4.33–4.27 (m, 2H),
2.04–1.90 (m, 2H), 1.60–1.50 (m, 2H), 1.47–1.35 (m, 4H), 0.95 ppm
(t, J=7.1 Hz, 3H); 13C NMR (100 MHz): d=156.3, 138.7, 133.5, 127.0,
121.8, 118.0, 117.6, 114.1, 67.9, 48.1, 31.4, 26.7, 26.6, 22.6, 14.0 ppm;
IR: n˜ =2953, 2923, 2858, 2208, 1605, 1580, 1555, 1506, 1492, 1481,
1456, 1381, 1344, 1291, 1267, 1202, 1178, 1146, 1114, 1057, 949,
924, 858, 850, 773, 754, 672, 666, 565, 554, 426 cmÀ1; HRMS (FAB):
m/z calcd for C22H22N3 [M+H]+: 328.1814; found: 328.1812; ele-
mental analysis calcd (%) for C22H21N3: C 80.70, H 6.46, N 12.83;
found: C 80.96, H 6.63, N 12.72.
1
a yellow solid. M.p. 116–1178C; H NMR (400 MHz): d=8.57 (brdd,
J=8.1, 1.7 Hz, 2H), 7.75–7.67 (m, 2H), 7.52–7.43 (m, 2H), 7.32–7.23
(m, 2H), 4.35–4.25 (m, 2H), 1.99–1.85 (m, 2H), 1.60–1.40 (m, 4H),
0.99 ppm (t, J=7.2 Hz, 3H); 13C NMR (100 MHz): d=177.9, 141.7,
133.8, 127.9, 122.4, 121.1, 114.5, 46.1, 28.9, 26.8, 22.5, 14.0 ppm; IR:
n˜ =3076, 2954, 2926, 2867, 1634, 1596, 1494, 1459, 1378, 1339,
1289, 1263, 1196, 1174, 1135, 1103, 1167, 1046, 972, 937, 866, 856,
802, 766, 751, 673, 644, 606, 570, 548, 458, 439, 413 cmÀ1; HRMS
(FAB): m/z calcd for C18H20ON [M+H]+: 266.1545; found: 266.1541;
elemental analysis calcd (%) for C18H20ON: C 81.47, H 7.22, N 5.28;
found: C 81.51, H 7.36, N 5.27.
Acknowledgements
This work was partly supported by JSPS KAKENHI grant
number 26410034.
Preparation of 2e
Keywords: acridones · crystal growth · molecular motion ·
structure–activity relationships · thermosalient effects
A mixture of 1e (1.14 g, 4.30 mmol) and malononitrile (3.25 g,
49.2 mmol) in Ac2O (100 mL) was stirred at 1308C for 21 h. After
evaporation under reduced pressure, the crude product was sub-
jected to column chromatography on silica gel (CHCl3) to give 2e
2123–2144; c) L. Dou, J. You, Z. Hong, Z. Xu, G. Li, R. A. Street, Y. Yang,
[2] a) M. H. Elsheikh, D. A. Shnawah, M. F. M. Sabri, S. B. M. Said, M. H.
Hassan, M. B. A. Bashir, M. Mohamad, Renewable Sustainable Energy Rev.
[3] a) H. J. Shepherd, I. A. Gural’skiy, C. M. Quintero, S. Tricard, L. Salmon, G.
Molnµr, A. Bousseksou, Nat. Commun. 2013, 4, 2607; b) Y. Liu, A. H.
Flood, P. A. Bonvallet, S. A. Vignon, B. H. Northrop, H.-R. Tseng, J. O. Jep-
pesen, T. J. Huang, B. Brough, M. Baller, S. Magonov, S. D. Solares, W. A.
(789 mg, 59%) as
a
brown solid. M.p. 166–1678C; 1H NMR
(400 MHz): d=8.55 (dd, J=8.3, 1.4 Hz, 2H), 7.71 (ddd, J=8.7, 7.1,
1.4 Hz, 2H), 7.47 (brd, J=8.7 Hz, 2H), 7.33 (ddd, J=8.2, 7.1, 1.0 Hz,
2H), 4.34–4.27 (m, 2H), 2.03–1.92 (m, 2H), 1.57–1.45 (m, 4H),
1.00 ppm (t, J=7.0 Hz, 3H); 13C NMR (100 MHz): d=156.2, 138.7,
133.5, 126.9, 121.7, 117.9, 117.6, 114.2, 67.6, 48.0, 28.9, 26.4, 22.3,
14.0 ppm; IR: n˜ =2205, 2193, 1602, 1577, 1554, 1504, 1489, 1457,
1380, 1338, 1291, 1262, 1199, 1179, 1115, 1055, 849, 777, 767, 750,
667, 571, 421 cmÀ1; HRMS (FAB): m/z calcd for C21H20N3 [M+H]+:
314.1657; found: 314.1654; elemental analysis calcd (%) for
C21H19N3: C 80.48, H 6.11, N 13.41; found: C 80.59, H 6.26, N 13.35.
Chem. Eur. J. 2016, 22, 7763 – 7770
7769
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