Total synthesis of 4-acetyl-1,3-dihydroimidazo[4,5-c]pyridin-2-one, a new microbial metabolite from a Streptomyces species.
The structure of a new secondary metabolite from Streptomyces sp. was determined as 4-acetyl-1,3-dihydroimidazo[4,5-c]pyridin-2-one by synthesis of the natural product itself and of the regioisomeric 7-acetylimidazo[4,5-b]pyridine derivative. The former compound was prepared, in 28% overall yield, in a sequence of nitration, reduction, condensation, and Stille reaction of 4-aminopyridine, while the regioisomer was obtained in 5% overall yield by amination, nitration, reduction, condensation, and oxidation of 4-ethylpyridine.
Bender
Tobias
T
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032 Marburg, Germany.
von Zezschwitz
Paultheo
P
D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011728:Pyridones / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013302:Streptomyces / Q000737:chemistry*
C543797:4-acetyl-1,3-dihydroimidazo(4,5-c)pyridin-2-one; D007093:Imidazoles; D007202:Indicators and Reagents; D011728:Pyridones