Base-Promoted N-Pyridylation of Heteroarenes Using N-Propargyl Enaminones as Equivalents of Pyridine Scaffolds

Guolin Cheng; Yunxiang Weng; Xifa Yang; Xiuling Cui

doi:10.1021/acs.orglett.5b01733

Base-Promoted N-Pyridylation of Heteroarenes Using N-Propargyl Enaminones as Equivalents of Pyridine Scaffolds

Org Lett. 2015 Aug 7;17(15):3790-3. doi: 10.1021/acs.orglett.5b01733. Epub 2015 Jul 22.

Authors

Guolin Cheng¹, Yunxiang Weng¹, Xifa Yang¹, Xiuling Cui¹

Affiliation

¹ Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China.

PMID: 26200227
DOI: 10.1021/acs.orglett.5b01733

Abstract

N-Pyridylation of various N-heteroarenes, including N-heteroarene-containing peptides, was achieved using N-propargyl enaminones (isolated or generated in situ from propargyl amine and propynones) as masked polysubstituted pyridine cores. This metal-free procedure proceeds under mild reaction conditions and generates 1 equiv of H2O as the sole byproduct.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Molecular Structure
Pargyline / analogs & derivatives
Pargyline / chemistry
Peptides / chemical synthesis
Propylamines / chemistry
Pyridines / chemical synthesis
Pyridines / chemistry*
Water / chemistry

Substances

Peptides
Propylamines
Pyridines
Water
propargylamine
Pargyline