Table 1. Preparation of Sulfonamide-Incorporated α-Aminophosphonates 20–34a.
| compd | R | yield (%)b | compd | R | yield (%)b |
|---|---|---|---|---|---|
| 5 | 4-Me | 71 | 20 | 4-Me | 56 |
| 6 | 4-Ph | 24 | 21 | 4-Ph | 41 |
| 7 | 4-OMe | 66 | 22 | 4-OMe | 51 |
| 8 | 4-SMe | 43 | 23 | 4-SMe | 60 |
| 9 | 4-F | 84 | 24 | 4-F | 67 |
| 10 | 4-Cl | 69 | 25 | 4-Cl | 66 |
| 11 | 4-Br | 58 | 26 | 4-Br | 45 |
| 12 | 3-F | 75 | 27 | 3-F | 37 |
| 13 | 3-Br | 87 | 28 | 3-Br | 31 |
| 14 | 2-F | 65 | 29 | 2-F | 57 |
| 15 | 2-NO2 | 41 | 30 | 2-NO2 | 42 |
| 16 | 2-OMe-6-Br | 93 | 31 | 2-OMe-6-Br | 56 |
| 17 | 2,5-(OMe)2 | 57 | 32 | 2,5-(OMe)2 | 69 |
| 18 | 3,4-(OMe)2 | 80 | 33 | 3,4-(OMe)2 | 59 |
| 19 | 2,4,5-(OMe)3 | 56 | 34 | 2,4,5-(OMe)3 | 63 |
Reagents and conditions: (i) DMF-DMA (1.2 equiv), DMF, 0 °C, 1 h, 25 °C, 2 h; (ii) aldehyde (3, 1 equiv), FeCl3 (20 mol %), dry DMF, 100 °C, 2 h; (iii) HP(O)(OEt)2 (1.2 equiv), dry DMF, 100 °C, 2 h; (iv) NH2NH2·xH2O (24–26%), DMF (or NMP), r.t., 1.5 h.
Isolated yields.
