Approaches to the Synthesis of 2,3-Dihaloanilines. Useful Precursors of 4-Functionalized-1H-indoles

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• 作者：Vero虂nica Guilarte ; M. Pilar Castroviejo ; Patricia Garci虂a-Garci虂a ; Manuel A. Ferna虂ndez-Rodri虂guez ; Roberto Sanz
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：May 6, 2011
• 年：2011
• 卷：76
• 期：9
• 页码：3416-3437
• 全文大小：1402K
• 年卷期：v.76,no.9(May 6, 2011)
• ISSN：1520-6904

文摘

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.