Current Organic Synthesis

L.-N. He
Nankai University
P.R. China


Smiles Rearrangement in Synthetic Chemistry

Author(s): Shuai Xia, Li-Ying Wang, Hua Zuo, Zhu-Bo Li.


Smiles rearrangement, an organic intramolecular nucleophilic aromatic substitution reaction, provides a powerful access to the synthesis of a variety of heterocyclic compounds. In contrast with the conventional protocols for the preparation of complex molecular structures, Smiles rearrangement, through the conversion of an easily-synthesized precursor into a desired “difficult-to-make’’ product, presents to be an extremely useful tool in organic synthesis. In the reactions, the yields of the Smiles rearrangement are profoundly influenced by electronic effect, steric effect and even the pH value. In this review, the detailed preparations of numerous molecules by taking advantage of Smiles rearrangement are discussed.

Keywords: Electronic effect, heterocycles, Meisenheimer complex, nucleophilic substitution, organic synthesis, steric effect, Smile rearrangement.

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Article Details

Year: 2013
Page: [935 - 946]
Pages: 12
DOI: 10.2174/15701794113106660081
Price: $58