A heavy metal- and oxidant-free, one-pot synthesis of pyridines and fused pyridines based on a Lewis acid-catalyzed multicomponent reaction.
The InCl3-catalyzed sequential multicomponent reaction between 2-furfurylamine, β-dicarbonyl compounds and α,β-unsaturated aldehydes in ethanol, followed by microwave irradiation in solvent-free conditions, afforded good to excellent yields of highly substituted pyridines, with loss of a 2-furylmethyl side chain. The method was also adapted to the synthesis of quinolones, isoquinolines, phenanthridines and more complex fused pyridine systems.
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain. josecm@farm.ucm.es.
V P Alex
VP
Raja
Giammarco
G
Tenti
Subbu
S
Perumal
J Carlos
JC
Menéndez
D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis*
D000447:Aldehydes; D000588:Amines; D058116:Lewis Acids; D011725:Pyridines