Table 2. Optimizations of Various Solvents for [3 + 2] Cycloaddition Reaction Using K3PO4 Basea.
entry | solvent | temperature (°C) | time (h) | oxazoline yield (%)c | oxazole yield (%)c |
---|---|---|---|---|---|
1 | DMF | 60 | 6 | 0 | 0 |
2 | DMSO | 60 | 6 | 0 | 0 |
3 | THF | 60 | 6 | 95 | 0 |
4 | CH3CN | 60 | 6 | 95 | 0 |
5 | CHCI3 | 60 | 6 | 50 | 40 |
6 | IPA-H2O | 60 | 4 | 10 | 80 |
7 | IPA | rt | 6 | 94 | 0 |
8 | EtOH | 60 | 1.5 | 0 | 92 |
9 | IPA | 60 | 1 | 0 | 95 |
10 | IPA | MWb, 65 | 0.13 | 0 | 96 |
Reaction was performed using 1a (1.18 mmol), 2a (1.18 mmol), and K3PO4 (2.36 mmol).
Microwave reactions were carried out in a microwave model no. CATA R (Catalyst Systems, Pune) at 65 °C using a power of 350 W.
Yield of the isolated product.