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.
Current Organic Synthesis
Title:Smiles Rearrangement in Synthetic Chemistry
Volume: 10 Issue: 6
Author(s): Shuai Xia, Li-Ying Wang, Hua Zuo and Zhu-Bo Li
Affiliation:
Keywords: Electronic effect, heterocycles, Meisenheimer complex, nucleophilic substitution, organic synthesis, steric effect, Smile rearrangement.
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.
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Cite this article as:
Xia Shuai, Wang Li-Ying, Zuo Hua and Li Zhu-Bo, Smiles Rearrangement in Synthetic Chemistry, Current Organic Synthesis 2013; 10 (6) . https://dx.doi.org/10.2174/15701794113106660081
DOI https://dx.doi.org/10.2174/15701794113106660081 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
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