Thiophene-3-boronic acid → 9-hydroxy-4-(3-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

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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-thienylboronic acid according to the procedure described in example 8 gave 9-hydroxy-4-(3-thienyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (12) (I, Ar=3-thienyl) in a 74% yield; mp 247° C. (dec). 1H NMR δ [(CD3)2SO] 11.73 (br s, 1H), 11.05 (br s, 1H), 9.24 (s, 1H), 9.15 (s, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.92 (dd, J=5.0, 2.7 Hz, 1H), 7.70 (s, 1H), 7.61 (dd, J=5.0, 2.7 Hz, 1H), 7.51 (dd, J=5.0, 0.9 Hz, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.06 (dd, J=8.7, 2.4 Hz, 1H). Found: C, 61.05; H, 2.96; N, 7.60. C18H10N2SO3,H2O requires C, 61.36; H, 3.43; N, 7.95.

Provenance & Evidence