Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share By
Efficient Synthesis of Novel 2-(2-Chloroquinolin-3-Yl)Imidazo[1,2-A]Pyridin-3-Amine Derivatives Publisher



Akbari M1 ; Maleki A2 ; Bahadorikhalili S3 ; Taayoshi F1 ; Adibpour N1 ; Mahdavi M3
Authors

Source: Journal of the Chinese Chemical Society Published:2021


Abstract

An efficient method is applied for the synthesis of novel 2-(2-chloroquinolin-3-yl)-N-alkylimidazo[1,2-a]pyridin-3-amine derivatives. The method is based on a two-step approach from acetanilide, 2-chloro-3-formyl quinoline, 2-aminopyridine, and isocyanide under mild reaction conditions. In the first step, acetanilide forms 2-chloroquinoline-3-carbaldehyde in the presence of phosphoryl chloride. The synthesized 2-chloroquinoline-3-carbaldehyde takes part in a multicomponent reaction with 2-aminopyridine, and isocyanide in the presence of trimethylsilyl chloride. The reaction is facile and the products are synthesized in high isolated yields under mild reaction conditions. © 2021 The Chemical Society Located in Taipei & Wiley-VCH GmbH
Related Docs
View other Related Docs
1. Advances and Applications of 2-Alkynylbenzaldoxime As a Valuable Synthetic Framework for Synthesizing N-Heterocycles, Tetrahedron (2023)
2. Combined Isocyanide-Based Multi-Component Ullmann-Type Reaction: An Efficient Access to Novel Nitrogen-Containing Pentacyclic Compounds, Molecular Diversity (2015)
3. Synthesis of Novel Fused Quinazolinone Derivatives, Molecular Diversity (2016)
Experts (# of related papers)
View all Related Experts
Mohammad Mahdavi (16)
Tahmineh Akbarzadeh (7)
Other Related Docs
4. Recent Advances in the Use of 2-Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N-Heterocycles, Advanced Synthesis and Catalysis (2024)
5. Novel Tacrine-Based Acetylcholinesterase Inhibitors As Potential Agents for the Treatment of Alzheimer’S Disease: Quinolotacrine Hybrids, Molecular Diversity (2022)
6. Palladium Functionalized Phosphinite Polyethyleneimine Grafted Magnetic Silica Nanoparticles As an Efficient Catalyst for the Synthesis of Isoquinolino[1,2-: B] Quinazolin-8-Ones, New Journal of Chemistry (2018)
7. Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity, Archiv der Pharmazie (2016)
8. Synthesis of Arylidene – Isoquinolinones Bearing Combretastatin Skeleton by Cyclocarbopalladation/Cross Coupling Tandem Heck-Suzuki Miaura Reactions Using Nano Catalyst Pd@Py-Il-Spion, Applied Organometallic Chemistry (2020)
9. Synthesis and Evaluation of Novel Oxoisoindoline Derivatives As Acetylcholinesterase Inhibitors, Monatshefte fur Chemie (2015)
10. Green Synthesis of 2-((2-Aryl-3-Oxoisoindolin-1-Yl)Methyl)Quinazolin-4(3H)-Ones Via Sequential Condensation, Sp3 C–H Bond Functionalization and Cyclization, Tetrahedron Letters (2018)
11. 6-Methoxy-1-Tetralone Derivatives Bearing an N-Arylpyridinium Moiety As Cholinesterase Inhibitors: Design, Synthesis, Biological Evaluation, and Molecular Docking Study, ChemistrySelect (2022)
12. Pd-Catalyzed Carbonylation-Cyclization of N′-(2-Bromophenyl)Benzami-Dines by Chloroform As a Co Precursor for the Synthesis of Quinazolin-4(3H)-Ones, Letters in Organic Chemistry (2020)
13. A One-Pot, Three-Component, Solvent-Free Synthesis of Novel 6H-Chromeno[3’,4’:5,6]Pyrido[2,3-D]Pyrimidine-Triones Under Microwave Irradiation, Journal of Chemical Research (2018)
14. Synthesis and Antibacterial Activity of New Chalcones Bearing an Imida-Zo[1,2-A]Pyridine Moiety, Current Chemical Biology (2021)
15. A Green and Efficient Synthesis of 2-Thioxoquinazolinone Derivatives in Water Using Potassium Thiocyanate, Journal of Sulfur Chemistry (2017)
16. Cubr/Et3n-Promoted Reactions of 2-Aminobenzamides and Isothiocyanates: Efficient Synthesis of Novel Quinazolin-4(3H)-Ones, Helvetica Chimica Acta (2016)
17. Synthesis, and in Vitro Biological Evaluations of Novel Naphthoquinone Conjugated to Aryl Triazole Acetamide Derivatives As Potential Anti-Alzheimer Agents, Journal of Molecular Structure (2022)
18. Transition Metal-Catalyzed C−H Activation/Functionalization of 8-Methylquinolines, Chemical Record (2024)
19. Potent Acetylcholinesterase Inhibitors: Design, Synthesis, Biological Evaluation, and Docking Study of Acridone Linked to 1,2,3-Triazole Derivatives, European Journal of Medicinal Chemistry (2015)
20. Rhodium-Catalyzed Transformations of Diazo Compounds Via a Carbene-Based Strategy: Recent Advances, RSC Advances (2024)