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. 2019 Mar 19;9(16):9093–9098. doi: 10.1039/c9ra01071h

Synthesis of pyrroles catalyzed by MIL-53(Al)a.

Entry Amine Time (min) Product Isolated yieldb (%)
1 graphic file with name c9ra01071h-u2.jpg 15 graphic file with name c9ra01071h-u3.jpg 96
2 graphic file with name c9ra01071h-u4.jpg 20 graphic file with name c9ra01071h-u5.jpg 86
3 graphic file with name c9ra01071h-u6.jpg 30 graphic file with name c9ra01071h-u7.jpg 85
4 graphic file with name c9ra01071h-u8.jpg 30 graphic file with name c9ra01071h-u9.jpg 88
5 graphic file with name c9ra01071h-u10.jpg 30 graphic file with name c9ra01071h-u11.jpg 80
6 graphic file with name c9ra01071h-u12.jpg 15 graphic file with name c9ra01071h-u13.jpg 96
7 graphic file with name c9ra01071h-u14.jpg 15 graphic file with name c9ra01071h-u15.jpg 98
8 graphic file with name c9ra01071h-u16.jpg 15 graphic file with name c9ra01071h-u17.jpg 95
9 graphic file with name c9ra01071h-u18.jpg 15 graphic file with name c9ra01071h-u19.jpg 98
10 graphic file with name c9ra01071h-u20.jpg 15 graphic file with name c9ra01071h-u21.jpg 98
11 graphic file with name c9ra01071h-u22.jpg 15 graphic file with name c9ra01071h-u23.jpg 75c
12 graphic file with name c9ra01071h-u24.jpg 20 graphic file with name c9ra01071h-u25.jpg 90
13 graphic file with name c9ra01071h-u26.jpg 15 graphic file with name c9ra01071h-u27.jpg 98
14 graphic file with name c9ra01071h-u28.jpg 15 graphic file with name c9ra01071h-u29.jpg 95
15 graphic file with name c9ra01071h-u30.jpg 15 graphic file with name c9ra01071h-u31.jpg 98
16 graphic file with name c9ra01071h-u32.jpg 15 graphic file with name c9ra01071h-u33.jpg 50
17 graphic file with name c9ra01071h-u34.jpg 20 graphic file with name c9ra01071h-u35.jpg Trace
18 graphic file with name c9ra01071h-u36.jpg 15 graphic file with name c9ra01071h-u37.jpg 55 (92)d
a

The reaction conditions: amines (1 mmol), acetonylacetone (1.2 mmol).

b

Isolated yield.

c

Yield of another isomer was obtained in 15%.

d

Yield in parenthesis was reported by the reaction with 2.4 equiv. of acetonylacetone.