2026-06-17T20:52:17Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/39132025-04-22T10:06:25Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Guilarte Moreno, Verónica Castroviejo Fernández, Mª Pilar García García, Patricia Fernández Rodríguez, Manuel A. Sanz Díez, Roberto 2016-01-27T09:24:07Z 2016-01-27T09:24:07Z 2011-03 0022-3263 http://hdl.handle.net/10259/3913 10.1021/jo200406f 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. Ministerio de Ciencia e Innovacion (MICINN) and FEDER (CTQ2010-15358) and Junta de Castilla y Leon (BU021A09 and GR-172) for financial support. V.G. thanks Ministerio de Educacion y Ciencia for a MEC-FPU predoctoral fellowship. P.G.-G. and M.A.F.-R. thank MICINN for "Juan de la Cierva" and "Ramon y Cajal" contracts. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. application/pdf eng American Chemical Society Journal of organic chemistry. 2010. V. 76, n. 9, p. 3416–3437 http://dx.doi.org/10.1021/jo200406f info:eu-repo/grantAgreement/MICINN-FEDER/CTQ2010-15358 info:eu-repo/grantAgreement/JCyL/BU021A09 info:eu-repo/grantAgreement/JCyL/GR-172 Química orgánica Chemistry, Organic Approaches to the synthesis of 2,3-dihaloanilines. Useful precursors of 4-functionalized-1 H-indoles info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion info:eu-repo/semantics/openAccess