Abstract
Background: Substituted 2-nitroanilines are synthetic intermediates used in the synthesis of important bioactive compounds. Nucleophilic aromatic substitution reactions with activated substrates, such as substituted 5-chloro-2-nitroanilines, usually involve the use of a solvent, high pressure conditions and prolonged reaction times. We describe a simple and straightforward protocol to prepare 5-substituted 2-nitroanilines that addresses these drawbacks.
Methods: Utilizing microwave irradiation and solvent free conditions, a series of 5-alkylamino-2- nitroanilines (1-14) have been efficiently prepared by reacting 4,5-dichloro-2-nitroaniline with different primary and cyclic secondary amines.
Results: The reactions proceeded in short periods of time (5-35 min) without side products, facilitating the isolation of 1- 14 in 55-93% yields. Reactions under microwave conditions were faster than those achieved with conventional heating.
Conclusion: This simplified approach can be a suitable alternative to synthetic methods involving conventional heating. The reported methodology can be applied to generate a variety of 5-substituted 2-nitroanilines which serve as precursors to compounds of pharmaceutical interest.
Keywords: 5-Substituted 2-nitroaniline, amine, green chemistry, microwave-assisted synthesis, nucleophilic aromatic substitution, solvent-free synthesis.
Current Microwave Chemistry
Title:Simplifying Nucleophilic Aromatic Substitutions: Microwave-Assisted Solvent Free Synthesis of 5-Alkylamino-2-nitroanilines
Volume: 3 Issue: 3
Author(s): Pedro J. Trejo-Soto, Anuar Flores-Gahona, Rafael Castillo and Alicia Hernández-Campos
Affiliation:
Keywords: 5-Substituted 2-nitroaniline, amine, green chemistry, microwave-assisted synthesis, nucleophilic aromatic substitution, solvent-free synthesis.
Abstract: Background: Substituted 2-nitroanilines are synthetic intermediates used in the synthesis of important bioactive compounds. Nucleophilic aromatic substitution reactions with activated substrates, such as substituted 5-chloro-2-nitroanilines, usually involve the use of a solvent, high pressure conditions and prolonged reaction times. We describe a simple and straightforward protocol to prepare 5-substituted 2-nitroanilines that addresses these drawbacks.
Methods: Utilizing microwave irradiation and solvent free conditions, a series of 5-alkylamino-2- nitroanilines (1-14) have been efficiently prepared by reacting 4,5-dichloro-2-nitroaniline with different primary and cyclic secondary amines.
Results: The reactions proceeded in short periods of time (5-35 min) without side products, facilitating the isolation of 1- 14 in 55-93% yields. Reactions under microwave conditions were faster than those achieved with conventional heating.
Conclusion: This simplified approach can be a suitable alternative to synthetic methods involving conventional heating. The reported methodology can be applied to generate a variety of 5-substituted 2-nitroanilines which serve as precursors to compounds of pharmaceutical interest.
Export Options
About this article
Cite this article as:
Trejo-Soto J. Pedro, Flores-Gahona Anuar, Castillo Rafael and Hernández-Campos Alicia, Simplifying Nucleophilic Aromatic Substitutions: Microwave-Assisted Solvent Free Synthesis of 5-Alkylamino-2-nitroanilines, Current Microwave Chemistry 2016; 3 (3) . https://dx.doi.org/10.2174/2213335603666151217181923
DOI https://dx.doi.org/10.2174/2213335603666151217181923 |
Print ISSN 2213-3356 |
Publisher Name Bentham Science Publisher |
Online ISSN 2213-3364 |
Call for Papers in Thematic Issues
Advance in Drug Delivery Carrier Microwave-Assisted Reactions for Enhanced Therapeutics and Diagnostic Purposes
Microwave irradiation technology has numerous applications in organic synthesis, pharmaceuticals, and the development of nanocarriers. To date, microwave-assisted reactions have garnered significant attention in synthesizing drug delivery carriers. Considering the advantages of microwave-assisted reactions, such as high percentage yield, shorter reaction time, and compound purity; microwave-assisted technology holds promise in ...read more
Microwave Technology: Advancements and Applications in Chemistry, Environment and Food Science
Microwave technology has emerged as a transformative tool in various fields, offering unique opportunities for rapid, efficient, and clean processes. This thematic issue aims to encapsulate the latest research, innovative strategies, and progressive methodologies concerning the application of microwave technology in three main areas: Chemistry: Highlighting the advancements in microwave-assisted ...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
-
<i>In Silico</i> Assessment of the Acute Toxicity of Chemicals: Recent Advances and New Model for Multitasking Prediction of Toxic Effect
Mini-Reviews in Medicinal Chemistry Fetal Distress Classification with Deep Convolutional Neural Network
Current Women`s Health Reviews Molecular Modeling and Dynamics Simulation Analysis of KATNAL1 for Identification of Novel Inhibitor of Sperm Maturation
Combinatorial Chemistry & High Throughput Screening Anticancer Evaluation of 3,4,5,4'-trans-tetramethoxystilbene (DMU-212) and Its Analogs Against an Extensive Panel of Human Tumor Cell Lines
Letters in Drug Design & Discovery Predicting the Efficacy of Novel Synthetic Compounds in the Treatment of Osteosarcoma <i>via</i> Anti-Receptor Activator of Nuclear Factor-κB Ligand (RANKL)/Receptor Activator of Nuclear Factor-κB (RANK) Targets
Medicinal Chemistry α-Glucosidase Inhibition and Docking Studies of 5-Deoxyflavonols and Dihydroflavonols Isolated from Abutilon pakistanicum
Current Organic Chemistry Repurposing FDA-approved Drugs Targeting SARS-CoV2 3CL<sup>pro</sup>: A Study by Applying Virtual Screening, Molecular Dynamics, MM-PBSA Calculations and Covalent Docking
Letters in Drug Design & Discovery Predicting Interactions Between Pathogen and Human Proteins Based on the Relation Between Sequence Length and Amino Acid Composition
Current Bioinformatics Non-Peptidic GnRH Receptor Antagonists
Current Medicinal Chemistry Progress in the Discovery of BACE Inhibitors
Current Pharmaceutical Design Other Activities
Current Bioactive Compounds Chemical and Biological Evaluation of Thiosemicarbazone-Bearing Heterocyclic Metal Complexes
Current Topics in Medicinal Chemistry Small Molecule Regulation of Stem Cells that Generate Bone, Chondrocyte, and Cardiac Cells
Current Topics in Medicinal Chemistry The Guanylyl Cyclase Inhibition by MB as Vasoplegic Circulatory Shock Therapeutical Target
Current Drug Targets Colloidal Polymeric Nanoparticles and Brain Drug Delivery
Current Drug Delivery Recent Updates on Biological Activities of Oxadiazoles
Mini-Reviews in Medicinal Chemistry <i>In Silico</i> Screening of Some Anti-Cancer Drugs Against the Main Protease of COVID-19 Using Molecular Docking
Letters in Organic Chemistry Inhibition of HIV-1 by Fusion Inhibitors
Current Pharmaceutical Design Dipeptidyl Peptidase IV Inhibitors: A New Paradigm in Type 2 Diabetes Treatment
Current Drug Targets Clinical Trials of Mesenchymal Stem Cells for the Treatment of COVID 19
Current Stem Cell Research & Therapy