4-Formylphenylboronic Acid → 4-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde

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The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 4-formylbenzeneboronic acid according to the procedure described in example 8 gave 4-(9-hydroxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-4-yl)benzaldehyde (509) (I; Ar=4-formylphenyl) in a 52% yield; mp (THF/CH2Cl2/pentane) 276–280° C. 1H NMR [(CD3)2SO] δ 11.84 (br s, 1H), 11.07 (br s, 1H), 10.11 (s, 1H), 9.28 (br s, 1H), 8.34 (d, J=2.3 Hz, 1H), 8.00 (d, J=8.2 Hz, 2H), 7.85 (d, J=8.1 Hz, 2H), 7.65 (s, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.08 (dd, J=8.7, 2.4 Hz, 1H). Found: C, 68.43; H, 4.16; N, 7.26. C21H12N2O4.3/4H2O requires C, 68.20; H, 3.68; N, 7.57. FABMS found [M+H]+: 357.0841. C21H13N2O4 requires 357.0875.

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