Table 2.
Synthesis of 1,5-disubstituted triazoles 3 a.
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Entry | 3 | R1 | R2 | R3 | R4 | Yield (%) b |
1 | 3a | H | H | H | H | 72 |
2 | 3b | Br | H | H | H | 85 |
3 | 3c | NO2 | H | H | H | 59 |
4 | 3d | H | H | Me | H | 60 |
5 | 3e | H | H | CF3 | H | 61 |
6 | 3f | H | H | F | H | 51 |
7 | 3g | H | H | Cl | H | 51 |
8 | 3h | H | H | Br | H | 66 |
9 | 3i | H | H | OMe | H | 60 |
10 | 3j | H | H | OEt | H | 51 |
11 | 3k | Br | H | OMe | H | 56 |
12 | 3l | Br | H | H | OMe | 38 |
13 | 3m | H | Br | OEt | H | 51 |
14 | 3n | H | Cl | OMe | H | 54 |
15 | 3o | H | OMe | OMe | H | 59 |
16 | 3p | H | Br | OH | H | 58 c |
17 | 3q | H | OH | OH | H | 71 c |
18 | 3r | H | OH | OMe | H | 69 c |
a General conditions: reactions were performed with 2 (0.5 mmol), EtMgCl (1.25 equiv.), and azide 1 (1 equiv.) in THF (0.45 M). b Isolated yields of triazoles 3 after flash column chromatography. c Global yield of two steps: formation of the triazole, followed by deprotection of OTBS groups with TBAF.