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. 2023 Aug 1;14(8):1067–1072. doi: 10.1021/acsmedchemlett.3c00200

Table 1. Preparation of Sulfonamide-Incorporated α-Aminophosphonates 2034a.

graphic file with name ml3c00200_0005.jpg

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
a

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.

b

Isolated yields.