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2005
Fused pyrrole derivatives
R 0160
Solvent Effects on the Oxidative Free Radical Reactions of 2-Amino-1,4-naphtho— Mn(O-Ac) 3-mediated coupling of 2-amino-1,4-naphthoquinones with
14- 127 quinones.
β-keto esters results in efficient formation of benzoindolediones or benzoindoletriones
depending on the solvent used. The reaction with simple ketones and α,β-unsaturated
ketones offers a convenient route to benzoindoles of type (VI) and (VIII). Treatment
with 2-cyclohexenones provides a novel route to benzocarbazole derivatives like (X)
and (XII). Best results are obtained using less acidic or neutral solvents. Under these
conditions the anilino derivative (XIII) can be transformed efficiently into benzoacridines. However, under more acidic conditions benzoindoles are formed. —
(TSENG, C.-M.; WU, Y.-L.; CHUANG*, C.-P.; Tetrahedron 60 (2004) 52,
12249-12260; Dep. Chem., Natl. Cheng Kung Univ., Tainan 70101, Taiwan; Eng.) —
Jannicke
2005
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