Synthesis of Polysubstituted Imidazo[1,2-a]pyridines via Microwave-Assisted One-Pot Cyclization/Suzuki Coupling/Palladium-Catalyzed Heteroarylation

• Published in: Journal of organic chemistry Vol. 72; no. 20; pp. 7650 - 7655
• Main Authors: Koubachi, Jamal, El Kazzouli, Saïd, Berteina-Raboin, Sabine, Mouaddib, Abderrahim, Guillaumet, Gérald
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.09.2007; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Cyclization; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Imidazoles - chemical synthesis; Microwaves; Organic chemistry; Palladium - chemistry; Physical Sciences; Preparations and properties; Pyridines - chemical synthesis; Science & Technology; C-NUCLEOSIDES; SELECTIVE LIGANDS; CROSS-COUPLING REACTION; IMIDAZO<1,2-A>PYRIDINE; PERIPHERAL BENZODIAZEPINE-RECEPTORS; BINDING-AFFINITY; ANTIVIRAL ACTIVITY; INHIBITORS; DERIVATIVES; P38 MAP KINASE; Suzuki coupling; Catalytic reaction; Amine; Imidazopyridine derivatives; Cyclization; Nitrogen heterocycle; Microwave; Palladium complex; Boron Organic compounds; Organic bromine compounds; Chemical synthesis; Boronic acids
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0712603

A new and efficient method for the synthesis of 2,3,6-trisubstituted imidazo[1,2-a]pyridine derivatives using a microwave-assisted one-pot, two-step Suzuki/heteroarylation or one-pot, three-step cyclization/Suzuki/heteroarylation was developed. Polysubstituted compounds are obtained in good yield from 2-amino-5-halogenopyridines, 2-halogenocarbonyl derivatives, boronic acids, and heteroaryl bromides.