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1. Total Synthesis of 4-Acetyl-1,3-Dihydroimidazo[4,5-c]Pyridin-2-One, a New Microbial Metabolite from a Streptomyces Species

Author

Tobias Bender and Paultheo von Zezschwitz

Subjects
Pharmacology, biology, Stereochemistry, Total synthesis, Plant Science, General Medicine, biology.organism_classification, Streptomyces, Stille reaction, chemistry.chemical_compound, Complementary and alternative medicine, chemistry, Nitration, Yield (chemistry), Drug Discovery, Pyridine, Derivative (chemistry), Amination
Abstract

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.

Published
2009
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