Abstract
A new synthesis of unsymmetrically substituted imidazo[1,2-a]quinoxalines via regioselective displacement of 3-chloro group in 2-(methylthio)-3-chloroquinoxalines by aminoacetaldehyde dimethylacetal and subsequent-acid mediated intramolecular cyclization of the resulting adducts is reported in this study. The utility of the 3-(methylthio) group in these imidazoquinoxalines is also demonstrated by conversion of one of the 2-(methylthio)quinoxalines to 2-(methylsulfonyl) derivative and its subsequent displacement by hydroxy-, phenoxy- and n-butylamino groups, thus affording various 2-substituted imidazo[1,2-a]quinoxalines.
Keywords: Imidazo[1, 2-a]quinoxalines, aminoacetaldehyde dimethylacetal, chloroquinoxalines, (methylsulfonyl)imidazo[1, 2- a]quinoxalines, anti-allergic, unsymmetrically.
Letters in Organic Chemistry
Title:Highly Regioselective Route to Substituted Imidazo[1,2-a]quinoxalines
Volume: 15 Issue: 5
Author(s): Balendu Singh, Anand Acharya and Hiriyakkanavar Ila*
Affiliation:
- New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bengaluru,India
Keywords: Imidazo[1, 2-a]quinoxalines, aminoacetaldehyde dimethylacetal, chloroquinoxalines, (methylsulfonyl)imidazo[1, 2- a]quinoxalines, anti-allergic, unsymmetrically.
Abstract: A new synthesis of unsymmetrically substituted imidazo[1,2-a]quinoxalines via regioselective displacement of 3-chloro group in 2-(methylthio)-3-chloroquinoxalines by aminoacetaldehyde dimethylacetal and subsequent-acid mediated intramolecular cyclization of the resulting adducts is reported in this study. The utility of the 3-(methylthio) group in these imidazoquinoxalines is also demonstrated by conversion of one of the 2-(methylthio)quinoxalines to 2-(methylsulfonyl) derivative and its subsequent displacement by hydroxy-, phenoxy- and n-butylamino groups, thus affording various 2-substituted imidazo[1,2-a]quinoxalines.
Export Options
About this article
Cite this article as:
Singh Balendu , Acharya Anand and Ila Hiriyakkanavar *, Highly Regioselective Route to Substituted Imidazo[1,2-a]quinoxalines, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178615666180108154309
DOI https://dx.doi.org/10.2174/1570178615666180108154309 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
![](/images/wayfinder.jpg)
- 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
-
Microbubble-Assisted p53, RB, and p130 Gene Transfer in Combination with Radiation Therapy in Prostate Cancer
Current Gene Therapy Heat Shock Protein 90 – a Potential Target in the Treatment of Human Acute Myelogenous Leukemia
Current Cancer Drug Targets Pharmacological Activation of p53 in Cancer Cells
Current Pharmaceutical Design CPP-mediated Protein Delivery in a Noncovalent Form: Proof-of-Concept for Percutaneous and Intranasal Delivery
Protein & Peptide Letters Single Autosomal Trisomy in Acute Myeloid Leukemia and Myelodysplastic Syndrome
Current Genomics Changes in Peripheral Blood Biomarkers with Aging and Neurodegenerative Disorders
Current Aging Science Ethanol Extract of Achillea fragrantissima Enhances Angiogenesis through Stimulation of VEGF Production
Endocrine, Metabolic & Immune Disorders - Drug Targets A Novel Multiple Tyrosine-kinase Targeted Agent to Explore the Future Perspectives of Anti-Angiogenic Therapy for the Treatment of Multiple Solid Tumors: Cabozantinib
Anti-Cancer Agents in Medicinal Chemistry Molecular Dynamics in Esophageal Adenocarcinoma: Who’s in Control?
Current Cancer Drug Targets Combating Mosquito-Borne Lymphatic Filariasis with Genomics Technologies: Enabling Novel Drug Discovery for Neglected Tropical Diseases
Current Pharmacogenomics and Personalized Medicine Topical Capsaicin for the Treatment of Neuropathic Pain
Current Drug Metabolism Brain Tumor Causes, Symptoms, Diagnosis and Radiotherapy Treatment
Current Medical Imaging Post-Translational Control of Sp-Family Transcription Factors
Current Genomics EZH2 RIP-seq Identifies Tissue-specific Long Non-coding RNAs
Current Gene Therapy Genetic Variants in Genes Involved in Mechanisms of Chemoresistance to Anticancer Drugs
Current Cancer Drug Targets Chemical and Biological Aspects of the Natural 1,4-Benzoquinone Embelin and its (semi-)Synthetic Derivatives
Current Medicinal Chemistry Matrix Metalloproteinases as Valid Clinical Target
Current Pharmaceutical Design Improving the Effect of FDA-Mandated Drug Safety Alerts with Internet- Based Continuing Medical Education
Current Drug Safety Developing a RiskScore Model based on Angiogenesis-related lncRNAs for Colon Adenocarcinoma Prognostic Prediction
Current Medicinal Chemistry NAD+ Metabolism and NAD+-Dependent Enzymes: Promising Therapeutic Targets for Neurological Diseases
Current Drug Targets