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. 2013 May 15;18(5):5580–5593. doi: 10.3390/molecules18055580

Table 3.

HCCP-mediated formation of quinazoline ethers from quinazolin-4(3H)-ones a. Inline graphic

Entry Quinazolin-4(3H)-one ArOH or RONa Product Yield (%) b
1 1a graphic file with name molecules-18-05580-i030.jpg graphic file with name molecules-18-05580-i031.jpg 18 75
2 1a graphic file with name molecules-18-05580-i032.jpg graphic file with name molecules-18-05580-i033.jpg 19 52
3 1a graphic file with name molecules-18-05580-i035.jpg graphic file with name molecules-18-05580-i037.jpg 20 73
4 1a graphic file with name molecules-18-05580-i038.jpg graphic file with name molecules-18-05580-i039.jpg 21 51
5 1b graphic file with name molecules-18-05580-i040.jpg graphic file with name molecules-18-05580-i046.jpg 22 53 c
6 1f graphic file with name molecules-18-05580-i047.jpg graphic file with name molecules-18-05580-i049.jpg 23 70
7 1g graphic file with name molecules-18-05580-i048.jpg graphic file with name molecules-18-05580-i059.jpg 24 70
8 1a CH3CH2ONa graphic file with name molecules-18-05580-i050.jpg 25 54
9 1b CH3CH2ONa graphic file with name molecules-18-05580-i051.jpg 26 33 c
10 1d CH3CH2ONa graphic file with name molecules-18-05580-i052.jpg 27 67
11 1g CH3CH2ONa graphic file with name molecules-18-05580-i053.jpg 28 64
12 1a CH3CH2CH2ONa graphic file with name molecules-18-05580-i054.jpg 29 48

a Reagents and Conditions: 1 (0.5 mmol), HCCP (1.1 equiv.), DIPEA (5.0 equiv.), MeCN (5 mL), rt, activation time (1 h), then phenols (5.0 equiv.), 45 °C, 23 h; or R2ONa (5.0 equiv.), 45 °C, 3 h; b Isolated yield; c Activation time (20 h).