title: Approaches to the synthesis of 2,3-dihaloanilines. Useful precursors of 4-functionalized-1H-indoles.
abstract: 2,3-Dihaloanilines have been proved as useful starting materials for synthesizing 4-halo-1H-indoles. Subsequent or in situ functionalization of the prepared haloindoles allows the access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles in good overall yields. As no efficient synthetic routes to 2,3-dihaloanilines have been described in the literature, different approaches to the preparation of these 1,2,3-functionalized aromatic precursors are now presented. The most general one involves a Smiles rearrangement from the corresponding 2,3-dihalophenols and allows the preparation of 2,3-dihaloanilides in a straightforward and synthetically useful manner.
authors: Departamento de Química, Área de Química Orgánica, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos, Spain.
authors: Verónica
authors: V
authors: Guilarte
authors: M Pilar
authors: MP
authors: Castroviejo
authors: Patricia
authors: P
authors: García-García
authors: Manuel A
authors: MA
authors: Fernández-Rodríguez
authors: Roberto
authors: R
authors: Sanz
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000814:Aniline Compounds; D006219:Halogens; D007211:Indoles; C023650:aniline