802
HETEROCYCLES, Vol. 67, No. 2, 2006
N, 17.49. Found: C, 67.42; H, 4.97; N, 17.52.
N-Dodecylacetamide (8): 2-Acetylaminopyrimidine (60 mg, 0.44 mmol) and dodecylamine (28 mg,
0
.15 mmol) in 15 mL of 1,2-dichloroethane were irradiated for 6 h as described in the general
photoacylation procedure, giving 8.8 mg (26%) of the product as a white solid (mp 49-52°C), TLC Rf
1
0
1
3
2
1
1
2
.17 (cyclohexane:EtOAc 1:2). H NMR (CDCl ) δ 5.40 (br s, 1H); 3.24 (q, J = 6.7 Hz, 2H), 1.98 (s, 3H),
3
1
3
.50 (quint, J = 7.2 Hz, 2H), 1.33-1.24 (18H), 0.89 (t, J = 6.9 Hz, 3H); C NMR (CDCl ) δ 169.9 (C),
3
9.7 (CH ), 31.9 (CH ), 29.62 (CH ), 29.57 (CH ), 29.53 (CH ), 29.33 (CH ), 29.29 (CH ), 26.9 (CH ),
2
2
2
2
2
2
2
2
3.4 (CH ), 22.7 (CH ), 14.1 (CH ). IR (neat) 3306.9, 3278.5, 2915.4, 2850.2, 1637.2, 1554.4, 1467.4,
3
2
3
+•
370.3, 1291.0, 720.6. MS m/z (%) 227 (19, M ), 212 (7), 198 (4), 184 (7), 170 (8), 156 (9), 142 (10),
28 (12), 114 (29), 100 (32), 86 (41), 73 (100), 72 (85), 60 (40); HR-MS 227.2247 (C H NO calcd
14
29
27.2249).
1
-Acetyl-7-azaindoline (9): A mixture of 1-acetyl-7-azaindole (7) (400 mg, 2.50 mmol) and 10%
palladium on charcoal in 30 mL of EtOH:DME (1:1) was stirred at rt under H for 5 h, then it was filtered
2
1
on celite and evaporated, to give 362 mg (89%) of the product as a white solid (mp 122-124°C). H NMR
(
CDCl ) δ 8.11 (d, J = 5.1 Hz, 1H), 7.46 (dq, J = 7.4, 1.4 Hz, 1H), 6.87 (dd, J = 7.3, 5.1 Hz, 1H), 4.11 (t,
3
13
J = 8.6 Hz, 2H), 3.06 (t, J = 8.6 Hz, 2H), 2.69 (s, 3H); C NMR (CDCl ) δ 170.1 (C), 156.1 (C), 146.1
3
(
CH), 133.3 (CH), 125.9 (C), 117.9 (CH), 45.5 (CH ), 24.8 (CH ), 24.2 (CH ). IR (neat) 2965.2, 2933.5,
2 3 2
2
911.3, 1645.6, 1584.9, 1411.8, 1384.4, 1322.4, 1238.8, 789.5. UV (51 µM soln in MeCN) λmax (ε) 197
+
•
(
0.59), 245 (0.64), 296 (0.50). MS m/z (%) 162 (22, M ), 120 (100), 119 (91), 93 (80), 65 (14); HR-MS
1
62.0782 (C H N O calcd 162.0793).
9 10 2
7
-Azaindole: A solution of 1-acetyl-7-azaindoline (11.4 mg, 70 µmol) and dodecylamine (13.0 mg, 70
µmol) in 7.5 mL of 1,2-dichloroethane was irradiated for 1 h as described in the general photoacylation
procedure, giving 2.1 mg (25%) of the product as a pale brown solid (mp 92-98°C), TLC R 0.21
f
1
(
cyclohexane:EtOAc 1:1). H NMR (CDCl ) δ 9.78 (br s, 1H), 8.34 (dd, J = 4.7, 1.6 Hz, 1H), 7.97 (dd, J
3
=
7.8, 1.5 Hz, 1H), 7.36 (dd, J = 3.3, 2.1 Hz, 1H), 7.11 (dd, J = 7.9, 4.7 Hz, 1H), 6.53 (dd, J = 3.5, 1.4 Hz,
13
1
H); C NMR (CDCl ) δ 148.5 (C), 143.0 (CH), 128.9 (CH), 124.8 (CH), 120.2 (C), 116.0 (CH), 101.0
3
(
CH). IR (neat) 3066.4, 2970.3, 2919.4, 2852.2, 2751.7, 1600.0, 1583.6, 1497.6, 1420.2, 1335.5, 1278.5,
+•
1
106.9, 901.1, 883.1. MS m/z (%) 118 (100, M ), 91 (56), 64 (24), 63 (23); HR-MS 118.0533 (C H N
7 6 2
calcd 118.0531).
2
-Acetylaminopyridine (11): A solution of 2-aminopyridine (10) (130 mg, 1.38 mmol) in acetic acid (4
mL) and acetyl chloride (1 mL) was stirred at reflux (ca. 90°C) for 2 h. An evaporation of the volatiles