title: A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and β-nitrostyrenes, via an unprecedented reaction sequence.
abstract: A six-step one-pot reaction was designed for synthesizing homodimeric 7-phenylindolo[3,2-a]carbazoles from 1H-indoles and β-nitrostyrenes, in the presence of SnCl(2)·2H(2)O. The reactions proceeded under very mild conditions and the desired heterocycles were obtained in moderate to good yields. An unprecedented mechanism involving sequential indole dimerization, regioselective nucleophilic conjugate addition of the resulting 2,3'-biindole to β-nitrostyrene and formal intramolecular [4 + 2]-cycloaddition is proposed.
authors: Laboratoire de Pharmacognosie, Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, UMR 8638 CNRS, Paris, France.
authors: Grégory
authors: G
authors: Dupeyre
authors: Pascale
authors: P
authors: Lemoine
authors: Nabila
authors: N
authors: Ainseba
authors: Sylvie
authors: S
authors: Michel
authors: Xavier
authors: X
authors: Cachet
mesh_terms: D002227:Carbazoles / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D003500:Cyclization; D019281:Dimerization; D007211:Indoles / Q000737:chemistry*; D049408:Luminescent Agents / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*; D017971:Tin Compounds / Q000737:chemistry
chemical_list: D002227:Carbazoles; D007211:Indoles; D049408:Luminescent Agents; D013343:Styrenes; D017971:Tin Compounds; C023599:stannous chloride; C011955:beta-nitrostyrene