Table 2.
Entry | R1 | R2 | R3 | Y | Product | T (°C) | Yield (%) | Yield (%) of catalytic methods [ref.] † |
---|---|---|---|---|---|---|---|---|
1 | Ph | H | H | EtO | 8a | 80 a | 91 | |
100 b | ||||||||
2 | Ph | H | H | MeO | 8b | 80 a | 80 | |
80 b | ||||||||
3 | Ph | H | H | Ph | 8c | 80 | 94 | |
4 | Bn | H | H | EtO | 8d | 100 | 81 | |
5 | Bn | H | H | Ph | 8e | 80 | 88 | |
6 | Ph | H | Ph | EtO | 8f | 100 | 93 | 98 [27], 85 [28], ~95 [29], 88 [30], 79 [31], 93 [32], 92 [33], ~90 [34], 96 [35], 60 [36], 86 [37], 92 [38] |
7 | Ph | H | Ph | MeO | 8g | 100 | 86 | 98 [24], 98 [27], 92 [33] |
8 | Ph | H | Ph | Ph | 8h | 80 | 87 | |
9 | Bn | H | Ph | EtO | 8i | 100 | 83 | 99 [28], 84 [29], 92 [30], 85 [31], 91 [32], 91 [33], 92 [35], 92 [36], 93 [38] |
10 | Bn | H | Ph | MeO | 8j | 100 | 87 | 95 [27], 82 [33] |
11 | Ph | Me | Ph | EtO | 8k | 120 | 80 | 75 [27], 74 [30], 63 [35], 18 [36] |
12 | Bn | Me | Ph | EtO | 8l | 120 | 84 | 92 [26], 80 [27], 81 [38] |
13 | Bn | Me | Ph | Ph | 8m | 100 a | 80 | |
120 b | 80 | |||||||
14 | Ph | EtO | 8n | 120 | 81 | 92 [27], ~72 [29], 86 [30], 47 [31], 87 [37] | ||
15 | Bn | EtO | 8o | 120 | 91 | 85 [26], 90 [27], 83 [31], 80 [33], 85 [38] | ||
16 | Bn | MeO | 8p | 120 | 85 | 92 [27] | ||
17 | Bn | Ph | 8q | 100 a | 80 | |||
120 b |
† for details see Table 3; a condensation of the oxo-component and the amine; b addition of the >P(O)H species to the Schiff-base.