通过Smiles重排由苯酚转化成苯胺

chem 有机方法 6.0W+ 0

通过Smiles重排由苯酚转化成苯胺  第1张

A novel one-pot synthesis of anilines from phenols was developed. Using this methodology, anilines are produced in good yield (86%) by a reaction of phenols with 2-bromo-2-methylpropionamide and NaOH in DMA via Smiles rearrangement. Phenols, which are substituted electron-withdrawing groups, are more reactive for Smiles rearrangement. Thiophenols are also converted to anilines. The process is a convenient, safe, and inexpensive method for large-scale preparation of anilines.


通过Smiles重排由苯酚转化成苯胺  第2张

合成应用:Novel Synthesis of 6-Amino-1-tetralonea

a Isolated yield = 59% (three-step, one-pot, only filtration).

通过Smiles重排由苯酚转化成苯胺  第3张

In summary, we have described a three-step, one-pot alkylation−rearrangement−hydrolysis procedure for the conversion of 6-hydroxy-1-tetralone 6 to 6-amino-1-tetralone 9. This is the simplest method to prepare 9. We then extended this method to the conversion of phenols or thiophenols to anilines, which have electron-withdrawing groups. This method produces a convenient, inexpensive, and scalable method of preparation of anilines. Additional examples of this three-step, one-pot alkylation−rearrangement−hydrolysis procedure will be the subject of a subsequent report.

Org. Lett. 2005, 7, 17, 3629–3631


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