Table 1.
Nitrogen functionalization of scaffolds 6 and 7.
| Entry | Scaffold | Functionalizing agent |
Product | Yield (%) |
|---|---|---|---|---|
| 1 | 6 | 20{1} | 8{1} | 95 |
| 2 | 6 | 20{2} | 8{2} | 96 |
| 3 | 6 | 20{3} | 8{3} | Quant. |
| 4 | 6 | 20{4} | 8{4} | 93 |
| 5 | 6 | 20{5} | 8{5} | 98 |
| 6 | 6 | 20{6} | 8{6} | 96 |
| 7 | 6 | 20{7} | 8{7} | 98 |
| 8 | 6 | 20{8} | 8{8} | 98 |
| 9 | 6 | 20{9} | 8{9} | 98 |
| 10 | 6 | 20{10} | 8{10} | 82a,b |
| 11 | 6 | 20{11} | 8{11} | 95 |
| 12 | 7 | 20{9} | 9{9} | 90 |
| 13 | 7 | 20{12} | 9{12} | 67 |
| 14 | 6 | 21{1} | 10{1} | 97 |
| 15 | 6 | 21{2} | 10{2} | 64 |
| 16 | 6 | 21{3} | 10{3} | 91 |
| 17 | 6 | 21{4} | 10{4} | 98 |
| 18 | 6 | 21{5} | 10{5} | 98 |
| 19 | 6 | 21{6} | 10{6} | 89 |
| 20 | 6 | 21{7} | 10{7} | 94 |
| 21 | 6 | 21{8} | 10{8} | 88 |
| 22 | 6 | 21{9} | 10{9} | 81 |
| 23 | 6 | 21{10} | 10{10} | 84 |
| 24 | 7 | 21{1} | 11{1} | 85 |
| 25 | 7 | 21{4} | 11{4} | 53 |
| 26 | 7 | 21{6} | 11{6} | 55 |
| 27 | 6 | 22{1} | 12{1} | 99 |
| 28 | 6 | 22{2} | 12{2} | 79 |
| 29 | 6 | 22{3} | 12{3} | 96 |
| 30 | 6 | 22{4} | 12{4} | 99 |
| 31 | 6 | 22{5} | 12{5} | 99 |
| 32 | 6 | 22{6} | 12{6} | 86 |
| 33 | 6 | 22{7} | 12{7} | 91 |
| 34 | 6 | 22{8} | 12{8} | Quant. |
| 35 | 6 | 22{9} | 12{9} | Quant. |
| 36 | 7 | 22{2} | 13{2} | 58 |
| 37 | 7 | 22{3} | 13{3} | 55 |
| 38 | 7 | 22{4} | 13{4} | Quant. |
| 39 | 6 | 23{1} | 14{1} | 99 |
| 40 | 6 | 23{2} | 14{2} | 98 |
| 41 | 6 | 23{3} | 14{3} | 98 |
| 42 | 6 | 23{4} | 14{4} | 83 |
| 43 | 6 | 23{5} | 14{5} | 94 |
| 44 | 6 | 23{6} | 14{6} | 95 |
| 45 | 6 | 23{7} | 14{7} | 90 |
| 46 | 7 | 23{1} | 15{1} | 79 |
| 47 | 7 | 23{3} | 15{3} | 83 |
| 48 | 7 | 23{7} | 15{7} | Quant. |
| 49 | 6 | 24{1} | 16{1} | 88 |
| 50 | 6 | 24{2} | 16{2} | 77 |
| 51 | 6 | 24{3} | 16{3} | 98 |
| 52 | 6 | 25{1} | 17{1} | 71 |
| 53 | 6 | 25{2} | 17{2} | Quant. |
| 54 | 6 | 25{3} | 17{3} | 98 |
| 55 | 6 | 25{4} | 17{4} | 83 |
| 56 | 6 | 25{5} | 17{5} | Quant. |
| 57 | 6 | 25{6} | 17{6} | 82 |
| 58 | 6 | 25{7} | 17{7} | 65 |
| 59 | 6 | 25{8} | 17{8} | 60 |
| 60 | 6 | 25{9} | 17{9} | 96 |
| 61 | 6 | 25{10} | 17{10} | 96 |
| 62 | 6 | 25{11} | 17{11} | 56c |
| 63 | 7 | 25{5} | 18{5} | 98 |
| 64 | 7 | 25{12} | 18{12} | 55 |
| 65 | 7 | 25{13} | 18{13} | 70 |
| 66 | 6 | 26{1} | 19{1} | 96 |
| 67 | 6 | 26{2} | 19{2} | 83 |
| 68 | 6 | 26{3} | 19{3} | 73 |
| 69 | 6 | 26{4} | 19{4} | 48 |
| 70 | 6 | 26{5} | 19{5} | 0 |
| 71 | 6 | 26{6} | 19{6} | 85c |
a
An additional 3.0 equivalents of Et3N were employed.
b
Isolated as the free-base.
c
No AcOH added.