4-(Hydroxymethyl)benzeneboronic acid → 9-hydroxy-4-(4-(hydroxymethyl)phenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Beteiligte Stoffe

Reaktionsschritte

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 4-hydroxymethylbenzeneboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(4-hydroxymethylphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (21) (I, Ar=4-hydroxymethylphenyl) in a 34% yield; mp 266–271° C. 1H NMR δ [(CD3)2SO] 11.74 (br s, 1H), 11.00 (br s, 1H), 9.25 (br s, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.56 (d, J=8.3 Hz, 2H), 7.56 (s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.40 (d, J=8.3 Hz, 1H), 7.06 (dd, J=8.7, 2.4 Hz, 1H), 5.27 (t, J=5.7 Hz, 1H), 4.59 (d, J=5.7 Hz, 2H). Found: C, 69.74; H, 4.04; N, 7.57. C21H14N2O4,1/4H2O requires C, 69.51; H, 4.02; N, 7.72.

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