Abstract
Imidoyl radicals (R1N=C.R2) are very attractive intermediates that can be readily produced by several methods, i.e. hydrogen atom abstraction from aldimines, homolytic fragmentation of certain imidoylic precursors, and addition of both carbon- and heteroatom-centered radicals to isonitriles and isothiocyanates. As far as their synthetic potential is concerned, they have been shown to perform smooth intra- and intermolecular additions to double and triple carbon-carbon bonds, as well as cyclizations onto aromatic rings, sulfur atoms, and cyano groups. They have been therefore efficiently employed in cyclizations, annulations, and cascade reactions leading to the construction of various nitrogen-containing heterocyclic compounds, e.g. indoles, phenanthridines, pyrrolidines, quinolines, quinoxalines, and fused polycyclic derivatives. They have been also used as key intermediates in the synthesis of carbonyl compounds, amides, and nitriles and as precursors of alkyl radicals in tin-free reactions. In this review we discuss thoroughly the generation methods, the structural features, and, above all, the reactivity of imidoyl radicals, with particular attention devoted to their synthetic applications.
Keywords: isothiocyanates, di-tert-butyl peroxide, electron withdrawing groups, azo-bis-iso-butyronitrile, benzophenone
Current Organic Chemistry
Title: Imidoyl Radicals in Organic Synthesis
Volume: 11 Issue: 15
Author(s): Matteo Minozzi, Daniele Nanni and Piero Spagnolo
Affiliation:
Keywords: isothiocyanates, di-tert-butyl peroxide, electron withdrawing groups, azo-bis-iso-butyronitrile, benzophenone
Abstract: Imidoyl radicals (R1N=C.R2) are very attractive intermediates that can be readily produced by several methods, i.e. hydrogen atom abstraction from aldimines, homolytic fragmentation of certain imidoylic precursors, and addition of both carbon- and heteroatom-centered radicals to isonitriles and isothiocyanates. As far as their synthetic potential is concerned, they have been shown to perform smooth intra- and intermolecular additions to double and triple carbon-carbon bonds, as well as cyclizations onto aromatic rings, sulfur atoms, and cyano groups. They have been therefore efficiently employed in cyclizations, annulations, and cascade reactions leading to the construction of various nitrogen-containing heterocyclic compounds, e.g. indoles, phenanthridines, pyrrolidines, quinolines, quinoxalines, and fused polycyclic derivatives. They have been also used as key intermediates in the synthesis of carbonyl compounds, amides, and nitriles and as precursors of alkyl radicals in tin-free reactions. In this review we discuss thoroughly the generation methods, the structural features, and, above all, the reactivity of imidoyl radicals, with particular attention devoted to their synthetic applications.
Export Options
About this article
Cite this article as:
Minozzi Matteo, Nanni Daniele and Spagnolo Piero, Imidoyl Radicals in Organic Synthesis, Current Organic Chemistry 2007; 11 (15) . https://dx.doi.org/10.2174/138527207782023120
DOI https://dx.doi.org/10.2174/138527207782023120 |
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
-
The Use of Citrullinated Peptides for the Diagnosis and Prognosis of Rheumatoid Arthritis
Current Topics in Medicinal Chemistry The Role of Exosomes in Infectious Diseases
Inflammation & Allergy - Drug Targets (Discontinued) New Pharmacological Approaches Using Polyphenols on the Physiopathology of Neuropathic Pain
Current Drug Targets Reactive Oxygen Production Induced by the Gut Microbiota: Pharmacotherapeutic Implications
Current Medicinal Chemistry Association of Oxidative Stress with Neurological Disorders
Current Neuropharmacology Risk Factors for Myocardial Infarction in Women and Men: A Review of the Current Literature
Current Pharmaceutical Design Oxidative Stress and Mitochondrial Impairment After Treatment with Anti-HIV Drugs: Clinical Implications
Current Pharmaceutical Design Fat and Aging: A Tale of Two Tissues
Current Aging Science Is Intake of Flavonoid-Based Food Supplements During Pregnancy Safe for the Developing Child? A Literature Review
Current Drug Targets Systemic Inflammation Induces Endothelial Dysfunction in Peritoneal Dialysis Patients
Vascular Disease Prevention (Discontinued) Adduct Formation and Context Factors in Drug Hypersensitivity: Insight from Proteomic Studies
Current Pharmaceutical Design Nitric Oxide and Dietary Factors: Part I Nitric Oxide Synthesis and Action
Vascular Disease Prevention (Discontinued) Transplantation Tolerance by Donor MHC Gene Transfer
Current Gene Therapy Zoledronic Acid: Pleiotropic Anti-Tumor Mechanism and Therapeutic Outlook for Osteosarcoma
Current Drug Targets Cannabinoid Signaling in Glial Cells in Health and Disease
Current Neuropharmacology Treatment of Inflammatory Diseases with Mesenchymal Stem Cells
Inflammation & Allergy - Drug Targets (Discontinued) Pharmacology of Appetite Suppression: Implication for the Treatment of Obesity
Current Drug Targets N-arylmethylideneaminophthalimide: Design, Synthesis and Evaluation as Analgesic and Anti-inflammatory Agents
Mini-Reviews in Medicinal Chemistry Peroxisome Proliferator-Activated Receptor γ Agonists as Insulin Sensitizers: From the Discovery to Recent Progress
Current Topics in Medicinal Chemistry Use of Novel m6A Regulator-mediated Methylation Modification Patterns in Distinct Tumor Microenvironment Profiles to Identify and Predict Glioma Prognosis and Progression, T-cell Dysfunction, and Clinical Response to ICI Immunotherapy
Current Pharmaceutical Design