Abstract
The photooxygenation of heterocycles represents a versatile and widely accepted tool for introducing oxygenated functions in a mild, simple and selective way. The review evidences the synthetic potential of the photooxygenation with particular attention to the reaction of Type II involving singlet oxygen in the first electronically excited state (1Δg), which has been applied to the most studied heterocycles as furans, thiophenes, pyrroles, oxazoles, imidazoles, indoles, nitrogen-containing six-membered systems. The singlet oxygenation of these systems occurs mainly via [4+2] cycloaddition leading to unstable endoperoxides which, in addition to the classical transformations of peroxides (reduction, hydrolysis, deoxygenation, generally performed at low temperature), afford characteristic rearranged products depending on the heteroatom, substitution pattern and experimental conditions. 1,2-Oxygen addition can sometimes compete with the Diels-Alder-type reaction, especially for pyrroles, imidazoles and indoles. The attention has been also focused to the oxygenation of some biomolecules as histidine, triptophan and guanine which play a significant role in biological processes as photodynamic effects or in the photoinduced deactivation of nucleic acids.
Keywords: synthesis, substrate, sensitizer, oxygenation, uv light
Current Organic Chemistry
Title: Photooxygenation of Heterocycles
Volume: 9 Issue: 2
Author(s): M. Rosaria Iesce, Flavio Cermola and Fabio Temussi
Affiliation:
Keywords: synthesis, substrate, sensitizer, oxygenation, uv light
Abstract: The photooxygenation of heterocycles represents a versatile and widely accepted tool for introducing oxygenated functions in a mild, simple and selective way. The review evidences the synthetic potential of the photooxygenation with particular attention to the reaction of Type II involving singlet oxygen in the first electronically excited state (1Δg), which has been applied to the most studied heterocycles as furans, thiophenes, pyrroles, oxazoles, imidazoles, indoles, nitrogen-containing six-membered systems. The singlet oxygenation of these systems occurs mainly via [4+2] cycloaddition leading to unstable endoperoxides which, in addition to the classical transformations of peroxides (reduction, hydrolysis, deoxygenation, generally performed at low temperature), afford characteristic rearranged products depending on the heteroatom, substitution pattern and experimental conditions. 1,2-Oxygen addition can sometimes compete with the Diels-Alder-type reaction, especially for pyrroles, imidazoles and indoles. The attention has been also focused to the oxygenation of some biomolecules as histidine, triptophan and guanine which play a significant role in biological processes as photodynamic effects or in the photoinduced deactivation of nucleic acids.
Export Options
About this article
Cite this article as:
Iesce Rosaria M., Cermola Flavio and Temussi Fabio, Photooxygenation of Heterocycles, Current Organic Chemistry 2005; 9 (2) . https://dx.doi.org/10.2174/1385272053369222
DOI https://dx.doi.org/10.2174/1385272053369222 |
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
-
Genomic Instability and Cancer
Current Molecular Medicine Patent Review
Combinatorial Chemistry & High Throughput Screening Signal Transduction through JAK-STAT and NF-κB Regulated Pim-1 Kinase: Novel Target for Anticancer Leads
Current Signal Transduction Therapy Promising Potential of Dietary (Poly)Phenolic Compounds in the Prevention and Treatment of Diabetes Mellitus
Current Medicinal Chemistry Lesson Learned from Nature for the Development of Novel Anti-Cancer Agents: Implication of Isoflavone, Curcumin, and their Synthetic Analogs
Current Pharmaceutical Design Pharmacokinetic and Toxicological Characteristics of Tripterigium Glycosides and Their Derivatives
Current Drug Metabolism Targeting Strategies for Glucose Metabolic Pathways and T Cells in Colorectal Cancer
Current Cancer Drug Targets Mending a Broken Heart: Bioengineered Patches and Scaffolds for Cardiac Repair
Recent Patents on Biomedical Engineering (Discontinued) Prader-Willi Syndrome: Clinical Genetics and Diagnostic Aspects with Treatment Approaches
Current Pediatric Reviews Structural Patterning Used for Polyfunctional Devices in Diagnostics and for the Delivery of Therapeutics
Recent Patents on Materials Science Myeloperoxidase as a Target for the Treatment of Inflammatory Syndromes: Mechanisms and Structure Activity Relationships of Inhibitors
Current Medicinal Chemistry Nanotech-based Food: An Initiative for Alternative Pharmaceuticals
Current Pharmaceutical Biotechnology Selective VEGFR Inhibitors for Anticancer Therapeutics in Clinical Use and Clinical Trials
Current Pharmaceutical Design Oesophagogastric Disconnection: Who, How and When? A Review Article
Current Pediatric Reviews Dose Sparing of CpG Oligodeoxynucleotide Vaccine Adjuvants by Nanoparticle Delivery
Current Drug Delivery The Serotonergic System: Its Role in Pathogenesis and Early Developmental Treatment of Autism
Current Neuropharmacology The Activating Receptors of Natural Killer Cells and Their Inter-Switching Potentials
Current Drug Targets Molecular Target-Guided Tumor Therapy with Natural Products Derived from Traditional Chinese Medicine
Current Medicinal Chemistry The Metastatic Process: Methodological Advances and Pharmacological Challenges
Current Medicinal Chemistry APP Transgenic Mouse Models and their Use in Drug Discovery to Evaluate Amyloid-β Lowering Therapeutics
CNS & Neurological Disorders - Drug Targets