3-Aminophenylboronic acid → 4-(3-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Participants

Reaction Steps

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 3-aminobenzeneboronic acid according to the procedure described in example 8 gave 4-(3-aminophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (15) (I, Ar=3-aminophenyl) in a 62% yield; mp 279–284° C. 1H NMR δ [(CD3)2SO] 11.70 (s, 1H), 10.96 (s, 1H), 9.22 (s, 1H), 8.33 (d, J=2.4 Hz, 1H), 7.50 (s, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.10–7.03 (m, 2H), 6.77–6.74 (m, 1H), 6.72–6.68 (m, 1H), 6.61 (dd, J=8.1, 2.3 Hz), 1H), 5.11 (br s, 2H). Found: C, 69.41; H, 4.12; N, 10.73. C20H13N3O3 requires C, 69.96; H, 3.82; N, 12.24.

Provenance & Evidence