Abstract
4-hydroxyquinolinones 7 were applied as 1,3-dinucleophiles in the reaction with Baylis-Hillman adduct acetates 6 to synthesize, in high yields of 75-92%, novel 2H-pyrano[3,2-c]quinoline-2,5(6H)-diones which are present in a number of biologically active compounds. The reaction was carried out under different conditions to achieve the optimum ones. The results indicated that acetonitrile as solvent and K2CO3 as base, under reflux conditions, were the optimum conditions. The reaction times are short and the experimental procedure is straightforward.
Keywords: 4-hydroxyqouinolone, Baylis–Hilmanadductacetates, pyranoquinolones, tandem reaction
Letters in Organic Chemistry
Title:An Efficient Synthesis of the 2H-pyrano[3,2-c]quinoline-2,5(6H)-dione System via Tandem Reaction of 4-hydroxyquinolinones to Baylis-Hillman Adduct Acetates
Volume: 9 Issue: 10
Author(s): Firouz M. Moghaddam, Behzad K. Foroushani and Elaheh L. Kalahroodi
Affiliation:
Keywords: 4-hydroxyqouinolone, Baylis–Hilmanadductacetates, pyranoquinolones, tandem reaction
Abstract: 4-hydroxyquinolinones 7 were applied as 1,3-dinucleophiles in the reaction with Baylis-Hillman adduct acetates 6 to synthesize, in high yields of 75-92%, novel 2H-pyrano[3,2-c]quinoline-2,5(6H)-diones which are present in a number of biologically active compounds. The reaction was carried out under different conditions to achieve the optimum ones. The results indicated that acetonitrile as solvent and K2CO3 as base, under reflux conditions, were the optimum conditions. The reaction times are short and the experimental procedure is straightforward.
Export Options
About this article
Cite this article as:
M. Moghaddam Firouz, K. Foroushani Behzad and L. Kalahroodi Elaheh, An Efficient Synthesis of the 2H-pyrano[3,2-c]quinoline-2,5(6H)-dione System via Tandem Reaction of 4-hydroxyquinolinones to Baylis-Hillman Adduct Acetates, Letters in Organic Chemistry 2012; 9 (10) . https://dx.doi.org/10.2174/157017812803901953
DOI https://dx.doi.org/10.2174/157017812803901953 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
- 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
-
The Immunoproteasome: An Emerging Therapeutic Target
Current Topics in Medicinal Chemistry Embryonic Stem Cell MicroRNAs: Defining Factors in Induced Pluripotent (iPS) and Cancer (CSC) Stem Cells?
Current Stem Cell Research & Therapy Endoglin-Targeted Cancer Therapy
Current Drug Delivery Pharmacophore Searching of Benzofuran Derivatives for Selective CYP19 Aromatase Inhibition
Letters in Drug Design & Discovery Inhibition of Aromatase (AR) by Benzyl Azole-Based Compounds
Letters in Drug Design & Discovery Synthetic Src-Kinase Domain Inhibitors and Their Structural Requirements
Anti-Cancer Agents in Medicinal Chemistry Cancer Immunotherapy: Battling Tumors with Gene Vaccines
Current Medicinal Chemistry - Anti-Inflammatory & Anti-Allergy Agents Bioactive Proteins and Peptides from Soybeans
Recent Patents on Food, Nutrition & Agriculture Anti-cancer Therapies in High Grade Gliomas
Current Proteomics Future Developments in Osteoporosis Therapy
Endocrine, Metabolic & Immune Disorders - Drug Targets Design, Synthesis and Anti-breast Cancer Activity of Some Novel Substituted Isoxazoles as Anti-breast Cancer Agent
Anti-Cancer Agents in Medicinal Chemistry Effective Inhibition of Foam Cells Formation by Tanshinone IIA in RAW264.7 Macrophages Induced with LDL Isolated from Hypercholesterolemia Patients: A Proteomic Analysis
Current Proteomics The Synergistic Effect of Humanized Monoclonal Antibodies Targeting Insulin-Like Growth Factor 1 Receptor (IGF-1R) and Chemotherapy
Current Drug Targets A Role of Immunotherapy in Metastatic Malignant Melanoma
Central Nervous System Agents in Medicinal Chemistry Distinctive Cellular Roles for Novel Protein Kinase C Isoenzymes
Current Pharmaceutical Design IBD Modern Concepts, Nano Drug Delivery and Patents: An Update
Recent Patents on Nanomedicine Pegylated Liposomal Doxorubicin in Salvage Chemotherapy for Multiple Myeloma Patients
Current Cancer Therapy Reviews Searching for Novel Cancer Chemopreventive Plants and their Products:The Genus Zanthoxylum
Current Drug Targets Editorial (Thematic Issue: Targeting Transporters for CNS Drug Delivery)
Current Pharmaceutical Design RNA Interference (RNAi) Patents and Human Health Related Applications of RNAi
Recent Patents on DNA & Gene Sequences