Synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation of 2-chloro-3-amino-heterocycles

Adam J. Rosenberg, Jinbo Zhao, Daniel A. Clark

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

A facile synthesis of imidazo[4,5-b]pyridines and-pyrazines is described using a Pd-catalyzed amide coupling reaction. This reaction provides quick access to products with substitution at N1 and C2. A model system relevant to the natural product pentosidine has been demonstrated, as well as the total synthesis of the mutagen 1-Me-5-PhIP.

Original languageEnglish (US)
Pages (from-to)1764-1767
Number of pages4
JournalOrganic Letters
Volume14
Issue number7
DOIs
StatePublished - Apr 6 2012

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Pyrazines
pyrazines
Mutagens
Palladium
Biological Products
Amides
palladium
pyridines
mutagens
synthesis
products
amides
Substitution reactions
substitutes
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
imidazo(4,5-b)pyridine
pentosidine

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation of 2-chloro-3-amino-heterocycles. / Rosenberg, Adam J.; Zhao, Jinbo; Clark, Daniel A.

In: Organic Letters, Vol. 14, No. 7, 06.04.2012, p. 1764-1767.

Research output: Contribution to journalArticle

Rosenberg, Adam J. ; Zhao, Jinbo ; Clark, Daniel A. / Synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation of 2-chloro-3-amino-heterocycles. In: Organic Letters. 2012 ; Vol. 14, No. 7. pp. 1764-1767.
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