Abstract
Chalcones belong to the flavonoid family which constitutes one of the major classes of naturally occurring oxygen heterocyclic compounds. The α,β-unsaturated carbonyl system of chalcones possesses two electrophilic reactive centers allowing them to participate in addition reactions via attack to the carbonyl group (1,2-addition) or involving the β-carbon (1,4-conjugate addition), leading to the synthesis of promising bioactive heterocyclic compounds. The purpose of this review is to present a systematic survey of the most recent literature that uses chalcones in the synthesis of biologically active 5- and 6-membered nitrogen heterocycles such as pyrroles, indoles, isoxazoles, imidazoles, pyrazoles, indazoles, triazoles, tetrazoles, pyridines and pyrimidines. Efficiency, easy-to-handle and cheap reagents, alternative heating conditions and greener protocols will be highlighted. In this review we will cover the literature since the beginning of the 21st century in more than 400 publications.
Keywords: Chalcones, cycloaddition reactions, Michael addition, nitrogen heterocyclic compounds, reactivity, synthetic methods.
Current Organic Chemistry
Title:Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles
Volume: 18 Issue: 21
Author(s): Helio M.T. Albuquerque, Clementina M.M. Santos, Jose A.S. Cavaleiro and Artur M.S. Silva
Affiliation:
Keywords: Chalcones, cycloaddition reactions, Michael addition, nitrogen heterocyclic compounds, reactivity, synthetic methods.
Abstract: Chalcones belong to the flavonoid family which constitutes one of the major classes of naturally occurring oxygen heterocyclic compounds. The α,β-unsaturated carbonyl system of chalcones possesses two electrophilic reactive centers allowing them to participate in addition reactions via attack to the carbonyl group (1,2-addition) or involving the β-carbon (1,4-conjugate addition), leading to the synthesis of promising bioactive heterocyclic compounds. The purpose of this review is to present a systematic survey of the most recent literature that uses chalcones in the synthesis of biologically active 5- and 6-membered nitrogen heterocycles such as pyrroles, indoles, isoxazoles, imidazoles, pyrazoles, indazoles, triazoles, tetrazoles, pyridines and pyrimidines. Efficiency, easy-to-handle and cheap reagents, alternative heating conditions and greener protocols will be highlighted. In this review we will cover the literature since the beginning of the 21st century in more than 400 publications.
Export Options
About this article
Cite this article as:
Albuquerque M.T. Helio, Santos M.M. Clementina, Cavaleiro A.S. Jose and Silva M.S. Artur, Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles, Current Organic Chemistry 2014; 18 (21) . https://dx.doi.org/10.2174/1385272819666141013224253
DOI https://dx.doi.org/10.2174/1385272819666141013224253 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...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
- Announcements
Related Articles
-
Closed-loop Neuropharmacology for Epilepsy: Distant Dream or Future Reality?
Current Neuropharmacology Adrenomedullin in Hypertension
Current Hypertension Reviews Developments in Selective Small Molecule ATP-Targeting the Serine/Threonine Kinase Akt/PKB
Mini-Reviews in Medicinal Chemistry Fluid and Electrolyte Disorders in the Newborn: Sodium and Potassium
Current Pediatric Reviews Development of Calorie Restriction Mimetics as Therapeutics for Obesity, Diabetes, Inflammatory and Neurodegenerative Diseases
Current Genomics Postprandial Hypotension - Novel Insights into Pathophysiology and Therapeutic Implications
Current Vascular Pharmacology Evidence-Based Pharmacological Treatment of Substance Use Disorders and Pathological Gambling
Current Drug Abuse Reviews Neuro-Immune-Endocrine Mechanisms During Septic Shock: Role For Nitric Oxide in Vasopressin and Oxytocin Release
Endocrine, Metabolic & Immune Disorders - Drug Targets Proteinase-Activated Receptor 2 (PAR2): A Challenging New Target for Treatment of Vascular Diseases
Current Pharmaceutical Design Evaluation of Endothelial (dys)Function, Left Ventricular Structure and Function in Patients with Chronic Kidney Disease
Current Vascular Pharmacology AMPA Glutamate Receptors and Neuropathic Pain
Mini-Reviews in Medicinal Chemistry Editorial: Limited Utility of the Handgrip Test for the Diagnosis of Diabetic Cardiovascular Autonomic Neuropathy: “There’s Time Enough, But None to Spare”
Current Vascular Pharmacology An Overview of the Pharmacological Properties and Potential Applications of Natural Monoterpenes
Mini-Reviews in Medicinal Chemistry Vascular Endothelial Growth Factor (VEGF) Biochemistry and Development of Inhibitory Drugs
Current Drug Therapy Using Structural and Mechanistic Information to Design Novel Inhibitors/Substrates of P-Glycoprotein
Current Topics in Medicinal Chemistry Cytoprotection and Immunomodulation in Cancer Therapy
Current Medicinal Chemistry - Anti-Cancer Agents Strategies that Target Tight Junctions for Enhanced Drug Delivery
Current Pharmaceutical Design Hydroxyimine NO-Donors; FK409 and Derivatives
Current Topics in Medicinal Chemistry Inhibition of Renin-Angiotensin System and Advanced Glycation End Products Formation: A Promising Therapeutic Approach Targeting on Cardiovascular Diseases
Cardiovascular & Hematological Agents in Medicinal Chemistry Relationship Between the Pharmacokinetics of Levosimendan and Its Effects on Cardiovascular System
Current Drug Metabolism