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. 2020 Dec 8;12(5):1886–1890. doi: 10.1039/d0sc05277a

Comparison tests of one-pot synthesis of 1,5-benzodiazepine 8aaavia a four-component domino reactiona.

graphic file with name d0sc05277a-u1.jpg
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
a

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.

b

Catalyst (10.00 mg).

c

Isolated yield in the first step.

d

Total isolated yield for the first two steps.

e

Overall isolated yield for the 3 steps.

f

The time taken for the reaction to complete.