- Approaches to the synthesis of 2,3-dihaloanilines. Useful precursors of 4-functionalized-1 H-indoles
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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.
- Guilarte, Veronica,Castroviejo, M. Pilar,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Sanz, Roberto
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p. 3416 - 3437
(2011/06/28)
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- Regioselective monobromination of substituted phenols in the presence of β-cyclodextrin
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Cyclodextrin acts as a restricting nanovessel to enhance regioselectivity in bromination of substituted phenols such as 3-nitrophenol, 2-chlorophenol, 3-chlorophenol, and 4-chlorophenol. In contrast to solution bromination, cyclodextrin facilitates regioselective monobromination and formation of polybrominated products are substantially reduced. Selectivities in brominations are also observed in water and in the solid state. The observed results are rationalized on the basis of specific modes of inclusion of substituted phenols inside the cyclodextrin cavity and find strong support from energy minimization studies and 1H-1H NOESY.
- Suresh, Palaniswamy,Annalakshmi, Subramanian,Pitchumani, Kasi
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p. 4959 - 4967
(2008/02/02)
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- A new and efficient synthesis of 4-functionalized benzo[6]furans from 2,3-dihalophenols
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Tandem Sonogashira coupling/5-endo-dig cyclization reactions on 2,3-dihalophenols suppose a straightforward entry to 4-halobenzo[b]furans, which can be easily transformed into 4-functionalized benzo[b]furans, that are difficult to synthesize by other proc
- Sanz, Roberto,Castroviejo, M. Pilar,Fernandez, Yolanda,Fananas, Francisco J.
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p. 6548 - 6551
(2007/10/03)
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