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. 2022 Aug 18;27(16):5285. doi: 10.3390/molecules27165285

Table 3.

The substrate scope of the AcOH-catalyzed three-component reaction between phenacyl alcohols 1417, oxoacetonitriles 2, 13, and 1820, and primary amines 3, 5, 6, 10, 11, and 21 for the selective synthesis of 3-cyanopyrroles 14ae, 15a, 16ab, and 17ab [a].

graphic file with name molecules-27-05285-i059.jpg

No. α-Hydroxyketon Oxoacetonitrile Amine 3-Cyanopyrrole Yield [b]
1 graphic file with name molecules-27-05285-i060.jpg graphic file with name molecules-27-05285-i061.jpg graphic file with name molecules-27-05285-i062.jpg graphic file with name molecules-27-05285-i063.jpg 90
2 graphic file with name molecules-27-05285-i064.jpg graphic file with name molecules-27-05285-i065.jpg graphic file with name molecules-27-05285-i066.jpg graphic file with name molecules-27-05285-i067.jpg 88
3 graphic file with name molecules-27-05285-i068.jpg graphic file with name molecules-27-05285-i069.jpg graphic file with name molecules-27-05285-i070.jpg graphic file with name molecules-27-05285-i071.jpg 86
4 graphic file with name molecules-27-05285-i072.jpg graphic file with name molecules-27-05285-i073.jpg graphic file with name molecules-27-05285-i074.jpg graphic file with name molecules-27-05285-i075.jpg 80
5 graphic file with name molecules-27-05285-i076.jpg graphic file with name molecules-27-05285-i077.jpg graphic file with name molecules-27-05285-i078.jpg graphic file with name molecules-27-05285-i079.jpg 77
6 graphic file with name molecules-27-05285-i080.jpg graphic file with name molecules-27-05285-i081.jpg graphic file with name molecules-27-05285-i082.jpg graphic file with name molecules-27-05285-i083.jpg 74
7 graphic file with name molecules-27-05285-i084.jpg graphic file with name molecules-27-05285-i085.jpg graphic file with name molecules-27-05285-i086.jpg graphic file with name molecules-27-05285-i087.jpg 82
8 graphic file with name molecules-27-05285-i088.jpg graphic file with name molecules-27-05285-i089.jpg graphic file with name molecules-27-05285-i090.jpg graphic file with name molecules-27-05285-i091.jpg 70
9 graphic file with name molecules-27-05285-i092.jpg graphic file with name molecules-27-05285-i093.jpg graphic file with name molecules-27-05285-i094.jpg graphic file with name molecules-27-05285-i095.jpg 84
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[a] A mixture of phenacyl alcohols 1417 (1.0 mmol), oxoacetonitriles 2, 13 and 1820 (1.0 mmol), and primary amines 3, 5, 6, 10, 11 and 21 (1.1 mmol) were stirred in EtOH (3 mL) at 70 °C for 3 h. [b] Isolated yields.