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

Table 2.

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

Entry Quinazolin-4(3H)-one ArSH Product Yield (%) b
1 graphic file with name molecules-18-05580-i001.jpg 1a graphic file with name molecules-18-05580-i011.jpg graphic file with name molecules-18-05580-i023.jpg 3 79
2 1a graphic file with name molecules-18-05580-i034.jpg graphic file with name molecules-18-05580-i041.jpg 4 64 c
3 1a graphic file with name molecules-18-05580-i042.jpg graphic file with name molecules-18-05580-i046.jpg 5 69
4 1a graphic file with name molecules-18-05580-i044.jpg graphic file with name molecules-18-05580-i045.jpg 6 59
5 1a graphic file with name molecules-18-05580-i002.jpg graphic file with name molecules-18-05580-i003.jpg 7 50
6 1a graphic file with name molecules-18-05580-i004.jpg graphic file with name molecules-18-05580-i005.jpg 8 86
7 1a graphic file with name molecules-18-05580-i006.jpg graphic file with name molecules-18-05580-i036.jpg 9 94
8 1a graphic file with name molecules-18-05580-i057.jpg graphic file with name molecules-18-05580-i007.jpg 10 66
9 1a graphic file with name molecules-18-05580-i008.jpg graphic file with name molecules-18-05580-i009.jpg 11 91
10 graphic file with name molecules-18-05580-i010.jpg 1b graphic file with name molecules-18-05580-i012.jpg graphic file with name molecules-18-05580-i013.jpg 12 54 d
11 graphic file with name molecules-18-05580-i014.jpg 1c graphic file with name molecules-18-05580-i015.jpg graphic file with name molecules-18-05580-i016.jpg 13 60
12 graphic file with name molecules-18-05580-i017.jpg 1d graphic file with name molecules-18-05580-i018.jpg graphic file with name molecules-18-05580-i019.jpg 14 64
13 graphic file with name molecules-18-05580-i020.jpg 1e graphic file with name molecules-18-05580-i021.jpg graphic file with name molecules-18-05580-i022.jpg 15 51 d
14 graphic file with name molecules-18-05580-i024.jpg 1f graphic file with name molecules-18-05580-i025.jpg graphic file with name molecules-18-05580-i026.jpg 16 79
15 graphic file with name molecules-18-05580-i027.jpg 1g graphic file with name molecules-18-05580-i028.jpg graphic file with name molecules-18-05580-i029.jpg 17 72

aReagents andConditions: 1 (0.5 mmol), HCCP (1.1 equiv.), DIPEA (5.0 equiv.), MeCN (5 mL), rt, activation time (1 h), then thiophenols (5.0 equiv.), 45 °C, 23 h; b Isolated yield; cm-CH3PhSH (6.0 equiv.); reaction time (48 h); d Activation time (20 h).