Abstract
Formerly, an unexpected acyl migration of 1-methylidene-3,4-dihydroisoquinoline- 2(1H)-yl-methanone derivatives was observed, and on this basis a microwave assisted synthetic method was developed for the preparation of members of the 2'-(3,4- dihydroisoquinoline-1-ylidene)-1-ethan-1-one family, potential CB2 receptor agonists and PDE7 inhibitors. The reaction mechanism was studied with experimental and theoretical methods in order to propose intra- and intermolecular radical pathways.
Keywords: Isoquinolines, acylation, fries-rearrangement, microwave synthesis, mechanism, radicals, quantum chemistry.
Current Organic Chemistry
Title:Synthetic and Mechanistic Study on the Microwave Assisted Fries Rearrangement of 1-Methylidene-3,4-dihydroisoquinoline-2(1H)-yl-methanones
Volume: 22 Issue: 9
Author(s): Flora Haraszti, Tamas Igricz, Gyorgy Keglevich*, Matyas Milen and Peter Abranyi-Balogh*
Affiliation:
- Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest,Hungary
- Hungarian Academy of Sciences, Research Centre for Natural Sciences, 1519 Budapest,Hungary
Keywords: Isoquinolines, acylation, fries-rearrangement, microwave synthesis, mechanism, radicals, quantum chemistry.
Abstract: Formerly, an unexpected acyl migration of 1-methylidene-3,4-dihydroisoquinoline- 2(1H)-yl-methanone derivatives was observed, and on this basis a microwave assisted synthetic method was developed for the preparation of members of the 2'-(3,4- dihydroisoquinoline-1-ylidene)-1-ethan-1-one family, potential CB2 receptor agonists and PDE7 inhibitors. The reaction mechanism was studied with experimental and theoretical methods in order to propose intra- and intermolecular radical pathways.
Export Options
About this article
Cite this article as:
Haraszti Flora , Igricz Tamas , Keglevich Gyorgy *, Milen Matyas and Abranyi-Balogh Peter*, Synthetic and Mechanistic Study on the Microwave Assisted Fries Rearrangement of 1-Methylidene-3,4-dihydroisoquinoline-2(1H)-yl-methanones, Current Organic Chemistry 2018; 22 (9) . https://dx.doi.org/10.2174/1385272822666180122155416
DOI https://dx.doi.org/10.2174/1385272822666180122155416 |
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
-
Resistance to Anti-VEGF Agents
Current Pharmaceutical Design The Molecular Control of Antigenic Variation in Trypanosoma brucei
Current Molecular Medicine Immunosuppressant Drugs and Covid-19: Associated Risks, Drug-Drug Interactions and Contraindications
Coronaviruses Nucleic Acid Aptamers Against Proteases
Current Medicinal Chemistry Deciphering the Physiology Underlying the Rapid Clinical Effects of Perispinal Etanercept in Alzheimers Disease
Current Alzheimer Research Systemic Vasculitis: An Epidemiological Perspective
Current Immunology Reviews (Discontinued) Thromboprophylaxis in Medical Patients: An Update
Vascular Disease Prevention (Discontinued) The Ca2+-Activated K+ Channel of Intermediate Conductance:A Molecular Target for Novel Treatments?
Current Drug Targets Manipulation of the Immune System for Cancer Defeat: A Focus on the T Cell Inhibitory Checkpoint Molecules
Current Medicinal Chemistry Lactoferrin as a Natural Immune Modulator
Current Pharmaceutical Design Venom Peptide Modulators of the Immune System
Inflammation & Allergy - Drug Targets (Discontinued) Progress in Studies of Structure, Mechanism and Antagonists Interaction of GPCR Co-Receptors for HIV
Current Pharmaceutical Biotechnology Improving of Nutraceutical Features of Many Important Mediterranean Vegetables by Inoculation with a New Commercial Product
Current Pharmaceutical Biotechnology New Strategies and Biological Agents in the Treatment of Autoimmune Inflammatory Diseases. Progress and Challenges
Immunology, Endocrine & Metabolic Agents in Medicinal Chemistry (Discontinued) Therapeutic Outlook of Pyrazole Analogs: A Mini Review
Mini-Reviews in Medicinal Chemistry Formulation and Characterizations of Delayed Release Multi-Particulates System of Indomethacin: Optimization by Response Surface Methodology
Current Drug Delivery Metal Allergens of Growing Significance: Epidemiology, Immunotoxicology, Strategies for Testing and Prevention
Inflammation & Allergy - Drug Targets (Discontinued) Specific Immune Intervention with Monoclonal Antibodies for the Treatment of Multiple Sclerosis
Current Medicinal Chemistry pH Modulation Based Solid Dispersion to Enhance Solubility of a Poorly Soluble NSAID - Development and Evaluation
Drug Delivery Letters Preface [Hot Topic: Matrix Metalloproteinase Inhibitors (Guest Editor: Jeremy I. Levin)]
Current Topics in Medicinal Chemistry