Table 3.
Library data for compounds 11{87–145}.
| compound | isocoumarin | reactant | methoda | yieldb (%) | purityd (%) |
|---|---|---|---|---|---|
| 11{87} | 11{68} | 15{1} | A | 70 | >99 |
| 11{88} | 11{68} | 15{2} | A | 66c | >99 |
| 11{89} | 11{68} | 15{3} | A | 59 | >99 |
| 11{90} | 11{68} | 15{4} | A | 59 | >99 |
| 11{91} | 11{68} | 15{5} | A | 49 | >99 |
| 11{92} | 11{68} | 15{6} | A | 74 | >99 |
| 11{93} | 11{68} | 15{7} | A | 74 | >99 |
| 11{94} | 11{68} | 15{8} | A | 75 | 99 |
| 11{95} | 11{68} | 15{9} | A | 76 | >99 |
| 11{96} | 11{68} | 15{10} | A | 55 | >99 |
| 11{97} | 11{68} | 15{11} | A | 77 | >99 |
| 11{98} | 11{69} | 15{1} | A | 64c | >99 |
| 1{99} | 11{69} | 15{3} | A | 88 | >99 |
| 11{100} | 11{69} | 15{4} | A | 89 | >99 |
| 11{101} | 11{69} | 15{5} | A | 45 | >99 |
| 11{102} | 11{69} | 15{8} | A | 52 | >99 |
| 11{103} | 11{69} | 15{9} | A | 76 | >99 |
| 11{104} | 11{69} | 15{10} | A | 45 | >99 |
| 11{105} | 11{69} | 15{11} | A | 62 | >99 |
| 11{106} | 11{70} | 15{1} | A | 37 | 94 |
| 11{107} | 11{70} | 15{2} | A | 37 | 97 |
| 11{108} | 11{70} | 15{3} | A | 35 | 97 |
| 11{109} | 11{70} | 15{4} | A | 38 | 99 |
| 11{110} | 11{70} | 15{5} | A | 33 | >99 |
| 11{111} | 11{70} | 15{6} | A | 38 | >99 |
| 11{112} | 11{71} | 15{1} | A | 36 | >99 |
| 11{113} | 11{71} | 15{2} | A | 23 | 98 |
| 11{114} | 11{71} | 15{3} | A | 29 | >99 |
| 11{115} | 11{71} | 15{4} | A | 14 | >99 |
| 11{116} | 11{71} | 15{5} | A | 20 | >99 |
| 11{117} | 11{71} | 15{6} | A | 21 | >99 |
| 11{118} | 11{78} | 15{1} | A | 90c | >99 |
| 11{119} | 11{78} | 15{2} | A | 21 | >99 |
| 11{120} | 11{78} | 15{3} | A | 65 | >99 |
| 11{121} | 11{78} | 15{4} | A | 45 | >99 |
| 11{122} | 11{78} | 15{5} | A | 60 | >99 |
| 11{123} | 11{78} | 15{7} | A | 40 | >99 |
| 11{124} | 11{78} | 15{12} | A | 14 | 95 |
| 11{125} | 11{79} | 15{1} | A | 58c | 99 |
| 11{126} | 11{79} | 15{2} | A | 80 | >99 |
| 11{127} | 11{79} | 15{3} | A | 58 | >99 |
| 11{128} | 11{79} | 15{4} | A | 79 | >99 |
| 11{129} | 11{79} | 15{5} | A | 72 | >99 |
| 11{130} | 11{79} | 15{6} | A | 67 | 99 |
| 11{131} | 11{79} | 15{7} | A | 82 | >99 |
| 11{132} | 11{79} | 15{9} | A | 20 | 97 |
| 11{133} | 11{79} | 15{10} | A | 8 | 99 |
| 11{134} | 11{68} | 16{1} | B | 86c | >99 |
| 11{135} | 11{68} | 16{2} | B | 42 | 99 |
| 11{136} | 11{68} | 16{3} | B | 68 | 98 |
| 11{137} | 11{69} | 16{1} | B | 39 | >99 |
| 11{138} | 11{69} | 16{2} | B | 17 | >99 |
| 11{139} | 11{78} | 16{2} | B | 61 | >99 |
| 11{140} | 11{79} | 16{1} | B | 68 | >99 |
| 11{141} | 11{79} | 16{2} | B | 67 | >99 |
| 11{142} | 11{68} | 17{1} | C | 17 | >99 |
| 11{143} | 11{68} | 17{3} | C | 12 | >99 |
| 11{144} | 11{69} | 17{3} | C | 13 | >99 |
| 11{145} | 11{78} | 17{2} | C | 37 | 95 |
a
Method A: RCOCl (1.3 equiv), Et3N (2 equiv), CH2Cl2, 0 °C to rt; Method B: (RCO2)2O (4 equiv), toluene, 110 °C; Method C: R2NCOCl (2 equiv), cat. DMAP, Et3N (3 equiv), CH2Cl2, 0 °C to 50 °C.
b
Isolated yield after preparative HPLC.
c
Isolated yield after column chromatography.
d
UV purity determined at 214 nm after preparative HPLC.