Current Organic Synthesis

Eduardo A. Castro
Universidad Nacional de La Plata
Buenos Aires


Smiles Rearrangement in Synthetic Chemistry

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

Affiliation: College of Pharmaceutical Sciences, Southwest University, Chongqing, 400715, China.

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


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.

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Article Details

Page: [935 - 946]
Pages: 12
DOI: 10.2174/15701794113106660081