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Current Organic Synthesis
ISSN (Print): 1570-1794
ISSN (Online): 1875-6271
VOLUME: 10
ISSUE: 6
DOI: 10.2174/15701794113106660081      Price:  $58









Smiles Rearrangement in Synthetic Chemistry

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Author(s): Shuai Xia, Li-Ying Wang, Hua Zuo and Zhu-Bo Li
Pages 935-946 (12)
Abstract:
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.
Affiliation:
College of Pharmaceutical Sciences, Southwest University, Chongqing, 400715, China.