Table 1. Effect of Base for [3 + 2] Cycloaddition Reaction in CH3OH Solventa.
entry | base | pKa | equiv | time | oxazoline yield (%)b3a | oxazole yield (%)b4a |
---|---|---|---|---|---|---|
1 | 12 h | 0 | 0 | |||
2 | triethylamine | 10.75 | 2 | 6 h | 95 | 0 |
3 | N,N-diisopropylethylamine | 10.74 | 2 | 6 h | 95 | 0 |
4 | imidazole | 6.9 | 2 | 6 h | 92 | 0 |
5 | N-methymorpholine | 7.4 | 2 | 6 h | 93 | 0 |
6 | NaHCO3 | 5.95 | 2 | 6 h | 90 | 0 |
7 | K2CO3 | 9.1 | 2 | 2 h | 0 | 94 |
8 | K3PO4 | 11.74 | 2 | 1.5 h | 0 | 95 |
Reaction was performed using 1a (1.18 mmol), 2a (1.18), and 2.36 mmol base.
Yield of the isolated product.