Route to Highly Substituted Pyridines

2016/08/31 by Justin A. Hilf, Michael S. Holzwarth, Scott D. Rychnovsky · 4 citations
Chemistry · #Catalytic C–H Functionalization Methods #Synthesis and Reactivity of Heterocycles #Synthesis of heterocyclic compounds

paper · doi:10.1021/acs.joc.6b01370

Abstract

Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines through a three-step procedure. Readily available enones are first converted into 1,5-dicarbonyls through a two-step Hosomi-Sakurai allylation/oxidative cleavage sequence, which is followed by subsequent cyclization to the corresponding pyridine using hydroxylamine hydrochloride. A variety of substituted pyridines have been synthesized using this method.

Cited by

• Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones. [europepmc]
• Recent Advances in Pyridine Scaffold: Focus on Chemistry, Synthesis, and Antibacterial Activities. [europepmc]
• Facile Synthesis of Polysubstituted Pyridines via Metal-Free [3+3] Annulation Between Enamines and β,β-Dichloromethyl Peroxides. [europepmc]
• Novel metallo-supramolecular architectures based on side-pyridine-modified terpyridines: design, self-assembly, and properties. [europepmc]

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