Table 1. Yields and Characterizing Data for 2-19
yield (%) mp (°C)
R
1H NMRb δ (ppm)
13C NMRb δ (ppm)
C6H5 (2)
100
122-124 7.37-7.87(m, 5H), 8.73 (br s, 1H, NH),
127.0, 128.7, 129.2, 132.2, 132.9,
8.77 (br s, 1H, NH)
142.1, 206.5 (CdSe)
golden needles
3-(H3C)C6H4 (3)
91
74-75
2.37 (s, 3H), 7.23-7.69 (m, 4H), 7.97
21.4, 123.7, 128.1, 128.5, 133.1,
(br s, 1H, NH), 8.88 (br s, 1H, NH)
138.6, 142.0, 207.9 (CdSe)
yellow needles
4-(H3C)C6H4 (4)
100
87
165-167 2.33 (s, 3H), 7.203-7.82 (m, 4H), 8.67
20.6, 127.4, 128.9, 139.5, 142.7,
206.5 (CdSe)
(br s, 1H, NH), 9.06 (br s, 1H, NH)
orange needles
2,6-Cl2C6H3 (5)
118-120 7.38-7.58 (m, 3H), 8.82 (br s, 1H, NH),
128.4, 129.1, 129.9, 135.0, 137.9,
9.51 (br s, 1H, NH)
202.3 (CdSe)
green needles
4-(NC)C6H4 (6)
65
151-153 7.72-7.95 (m, 4H), 8.68 (br s, 1H, NH),
114.2, 118.4, 127.5, 132.3, 146.5,
9.38 (br s, 1H, NH)
205.4 (CdSe)
orange needles
3-(NC)C6H4 (7)
80
132-134 7.55-8.17 (m, 4H), 8.08 (br s, 1H, NH),
112.1, 129.4, 130.5, 131.6, 134.6,
9.33 (br s, 1H, NH)
143.7, 204.7 (CdSe)
brown needles
4-(O2N)C6H4 (8)
90
104-105 6.61-8.31 (m, 4H), 8.95 ((br s, 1H, NH),
113.95, 123.4, 128.0, 133.7, 148.2,
9.43 (br s, 1H, NH)
204.9 (CdSe)
yellow needles
3,4-(H3CO)2C6H3 (9)
2.17 (s, 3H), 3.85 (s, 3H), 6.91-7.60 (m, 3H), 55.5, 55.6, 110.5, 11.4, 121.2, 134.2,
8.65 (br s, 1H, NH), 8.93 (br s, 1H, NH)
148.4, 205.2 (CdSe)
yellow needles
67
60
177-179
175-176
154-155
3.84, (s, 3H), 3.86 (s, 3H), 6.60 (s, 1H), 7.51
(d, J ) 9.6 Hz, 1H), 8.58 (d, J ) 8.9 Hz, 1H), 134.9, 140.6, 204.1 (CdSe)
9.10 (br s, 1H, NH), 9.35 (br s, 1H, NH)
55.7, 56.0, 98.0, 98.6, 106.2, 106.5,
2,4-(H3CO)2C6H3 (10)
red needles
2,3-(H3CO)2C6H3 (11)
3.80 (s, 3H), 3.85 (s, 3H), 7.04-7.59 (m, 3H), 60.4, 61.2, 115.1, 123.6, 124.2, 124.7,
9.37 (br s, 1H, NH), 9.60 (br s, 1H, NH)
124.9, 203.4 (CdSe)
yellow needles
4-(H3CO)C6H4 (12)
82
98
138-140 3.83 (s, 3H), 6.90-7.95(m, 4H), 8.59
55.4, 113.4, 129.7, 134.2, 163.0,
(br s, 1H, NH), 8.93 (br s, 1H, NH)
205.0 (CdSe)
greenish yellow needles
3-(H3CO)C6H4 (13)
100
100
95
99-100
3.88 (s, 3H), 7.11-7.43 (m, 4H), 8.77
(br s, 1H, NH), 9.18 (br s, 1H, NH)
55.3, 112.5, 119.5, 129.4, 206.8 (CdSe)
orange needles
2-(H3CO)C6H4 (14)
185-186 3.91 (s, 3H), 6.99-8.38 (m, 4H), 9.09
55.8, 111.9, 120.6, 133.3, 136.5,
154.9, 203.6 (CdSe)
(br s, 1H, NH), 9.49 (br s, 1H, NH),
green needles
4-ClC6H4 (15)
124-126 7.38-7.88 (m, 4H), 8.77 (br s, 1H, NH),
128.3, 128.9, 137.3, 141.1, 205.4 (CdSe)
9.21 (br s, 1H, NH)
orange needles
3-ClC6H4 (16)
68
125-127 7.38-7.87 (m, 4H), 8.76 (br s, 1H, NH),
125.6, 127.1, 129.9, 131.2, 133.7,
9.30 (br s, 1H, NH)
144.4, 205.3 (CdSe)
yellow needles
2-ClC6H4 (17)
100
89
46-48
7.26-7.78 (m, 4H), 8.79 (br s, 1H, NH),
9.47 (br s, 1H, NH)
126.8, 127.8, 130.1, 134.5, 134.6,
144.7, 206.0 (CdSe)
orange solids
4-FC6H4 (18)
136-138 7.09-7.97 (m, 4H), 8.72 (br s, 1H, NH),
114.9, 115.2, 138.9, 162.9, 166.7,
9.19 (br s, 1H, NH)
205.3 (CdSe)
yellow needles
4-BrC6H4 (19)
92
137-139 7.54-7.79 (m, 4H), 8.75 (br s, 1H, NH),
125.9, 129.0, 131.3, 141.5, 205.5 (CdSe)
9.23 (br s, 1H, NH)
orange needles
a Satisfactory microanalyses obtained for all compounds: C ( 0.15, H ( 0.10, N ( 0.10. b Acetonitrile-d3 was used at 25 °C for all compounds.
solvent was removed in vacuo, and the residue was purified
ethyl acetate eluant) and recrystallization from dichlo-
by column chromatography (silica gel 9:1 ) dichloromethane/
romethane/n-hexane.
5252
Org. Lett., Vol. 8, No. 23, 2006