Comparison tests of one-pot synthesis of 1,5-benzodiazepine 8aaavia a four-component domino reactiona.
Entry | Catalystb | t 1 f (h) | Yieldc (%) 3a | t 2 f (h) | Yieldd (%) 5aa | T 3 (°C) | t 3 f (min) | Yielde (%) 8aaa |
---|---|---|---|---|---|---|---|---|
1 | Al6{P4Mo6}6 | 3.0 | 98 | 1.8 | 92 | 25 | 20 | 83 |
2 | Al{P4Mo6}2 | 3.2 | 97 | 2.0 | 89 | 25 | 20 | 75 |
3 | No catalyst | 7.0 | 98 | 5.5 | 62 | 25 | 120 | Trace |
4 | p-TsOH | 4.0 | 92 | 3.0 | 73 | 25 | 26 | 43 |
5 | AlCl3 | 4.5 | 94 | 3.0 | 82 | 25 | 58 | 29 |
6 | {Na[P4Mo6]2} | 3.5 | 95 | 2.5 | 86 | 25 | 30 | 72 |
One-pot reaction conditions: acetophenone 1a (1.00 mmol), N,N-dimethylformamide dimethyl acetal 2 (1.00 mmol), 1,2-phenylenediamine 4a (1.00 mmol), ethyl pyruvate 6a (1.00 mmol) and catalyst (10.00 mg) for the four-component domino reaction.
Catalyst (10.00 mg).
Isolated yield in the first step.
Total isolated yield for the first two steps.
Overall isolated yield for the 3 steps.
The time taken for the reaction to complete.