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. Author manuscript; available in PMC: 2010 Jul 9.
Published in final edited form as: J Med Chem. 2009 Jul 9;52(13):4038–4053. doi: 10.1021/jm900356n

Table 1.

Synthesis of 2-Ethenyl Derivatives of 5-NI by Aldol Condensation

graphic file with name nihms124235f8.jpg
entry aldehyde product yield (%) entry Aldehyde product yield (%)
1 Benzaldehyde graphic file with name nihms124235t1.jpg
5
20 15 3-fluoro-benzaldehyde graphic file with name nihms124235t2.jpg
19
13
2 2-methyl-benzaldehyde graphic file with name nihms124235t3.jpg
6
23 16 3-methoxy-benzaldehyde graphic file with name nihms124235t4.jpg
20
32
3 3-methyl-benzaldehyde graphic file with name nihms124235t5.jpg
7
42 17 4-trifluoro-methoxy-benzaldehyde graphic file with name nihms124235t6.jpg
21
14
4 4-methyl-benzaldehyde graphic file with name nihms124235t7.jpg
8
22 18 2,3,4-trimethoxy-benzaldehyde graphic file with name nihms124235t8.jpg
22
16
5 2,4,6-trimethyl-benzaldehyde graphic file with name nihms124235t9.jpg
9
29 19 4-diethoxy-methyl-benzaldehyde graphic file with name nihms124235t10.jpg
23
24
6 2-bromo-benzaldehyde graphic file with name nihms124235t11.jpg
10
20 20 2-biphenyl-carbaldehyde graphic file with name nihms124235t12.jpg
24
21
7 3-bromo-benzaldehyde graphic file with name nihms124235t13.jpg
11
19 21 1-napthyl-aldehyde graphic file with name nihms124235t14.jpg
25
28
8 4-bromo-benzaldehyde graphic file with name nihms124235t15.jpg
12
72 22 2-napthyl-aldehyde graphic file with name nihms124235t16.jpg
26
19
9 2-chloro-benzaldehyde graphic file with name nihms124235t17.jpg
13
24 23 piperonal graphic file with name nihms124235t18.jpg
27
31
10 3-chloro-benzaldehyde graphic file with name nihms124235t19.jpg
14
19 24 1-methyl-imidazole-2-carbaldehyde graphic file with name nihms124235t20.jpg
28
77
11 4-chloro-benzaldehyde graphic file with name nihms124235t21.jpg
15
15 25 furan-2-carbaldehyde graphic file with name nihms124235t22.jpg
29
53
12 2,4-dichloro-benzaldehyde graphic file with name nihms124235t23.jpg
16
15 26 2-thiophene-carbaldehyde graphic file with name nihms124235t24.jpg
30
23
13 2-iodo-benzaldehyde graphic file with name nihms124235t25.jpg
17
20 27 3-thiophene-carbaldehyde graphic file with name nihms124235t26.jpg
31
22
14 3-iodo-benzaldehyde graphic file with name nihms124235t27.jpg
18
19