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.
Export Options
About this article
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 |
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Painful Peripheral Neuropathies
Current Neuropharmacology Regulation of Neutrophil Apoptosis and Removal of Apoptotic Cells
Current Drug Targets - Inflammation & Allergy Heat Shock Paradox and a New Role of Heat Shock Proteins and their Receptors as Anti-Inflammation Targets
Inflammation & Allergy - Drug Targets (Discontinued) Farnesyltransferase Inhibitors: A Comprehensive Review Based on Quantitative Structural Analysis
Current Medicinal Chemistry Annexins in the Central Nervous System: Are they Neuroprotective or Proapoptotic Agents?
Medicinal Chemistry Reviews - Online (Discontinued) Pomegranate Use to Attenuate Bone Loss in Major Musculoskeletal Diseases: An Evidence-Based Review
Current Drug Targets Sepsis-induced Cardiomyopathy
Current Cardiology Reviews An Original Deal for New Molecule: Reversal of Efflux Pump Activity, A Rational Strategy to Combat Gram-Negative Resistant Bacteria
Current Medicinal Chemistry Synergies of Virtual Screening Approaches
Mini-Reviews in Medicinal Chemistry In Silico Study of Chromatographic Lipophilicity Parameters of 3-(4-Substituted Benzyl)-5-Phenylhydantoins
Combinatorial Chemistry & High Throughput Screening Shared Food, Meals and Drinks: 10 Arguments Suggesting an Oral Transmission Route of SARS-CoV-2
Infectious Disorders - Drug Targets Current Status and Perspectives in the Development of Camptothecins
Current Pharmaceutical Design Matrix Metalloproteinases and their Tissue Inhibitors in Diabetes, Atherosclerosis and Prediction of the Cardiovascular Risk
Current Enzyme Inhibition The Antimitotic Potential of PARP Inhibitors, An Unexplored Therapeutic Alternative
Current Topics in Medicinal Chemistry Phytochemical and Pharmacological Investigation of Cassia Siamea Lamk: An Insight
The Natural Products Journal Utilizing Peptide Structures As Keys For Unlocking Challenging Targets
Mini-Reviews in Medicinal Chemistry A Further Step Toward an Optimal Ensemble of Classifiers for Peptide Classification, a Case Study: HIV Protease
Protein & Peptide Letters Advancements in COVID-19 Testing: An In-depth Overview
Current Pharmaceutical Biotechnology Correlations between Insomnia and Sex, Work Experience, Shift and Body Max Index in Italian Nurses: A Scoping Profile Statement
Endocrine, Metabolic & Immune Disorders - Drug Targets Synopsis of Pharmotechnological Approaches in Diagnostic and Management Strategies for Fighting Against COVID-19
Current Pharmaceutical Design