Table 2.
HCCP-mediated formation of quinazoline thioethers from quinazolin-4(3H)-ones a.
Entry | Quinazolin-4(3H)-one | ArSH | Product | Yield (%) b | ||
---|---|---|---|---|---|---|
1 |
![]() |
1a |
![]() |
![]() |
3 | 79 |
2 | 1a |
![]() |
![]() |
4 | 64 c | |
3 | 1a |
![]() |
![]() |
5 | 69 | |
4 | 1a |
![]() |
![]() |
6 | 59 | |
5 | 1a |
![]() |
![]() |
7 | 50 | |
6 | 1a |
![]() |
![]() |
8 | 86 | |
7 | 1a |
![]() |
![]() |
9 | 94 | |
8 | 1a |
![]() |
![]() |
10 | 66 | |
9 | 1a |
![]() |
![]() |
11 | 91 | |
10 |
![]() |
1b |
![]() |
![]() |
12 | 54 d |
11 |
![]() |
1c |
![]() |
![]() |
13 | 60 |
12 |
![]() |
1d |
![]() |
![]() |
14 | 64 |
13 |
![]() |
1e |
![]() |
![]() |
15 | 51 d |
14 |
![]() |
1f |
![]() |
![]() |
16 | 79 |
15 |
![]() |
1g |
![]() |
![]() |
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).