Jump to main content
Jump to site search

Issue 9, 2019
Previous Article Next Article

A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones

Author affiliations

Abstract

A new method for the synthesis of 2,4,5-trisubstituted pyridines from N-propargylic β-enaminothiones is reported. β-Enaminothiones were prepared by thionation of the corresponding β-enaminones with Lawesson's reagent. When treated with diisopropylamine in DMF at room temperature, N-propargylic β-enaminothiones yielded 2,4,5-trisubstituted pyridines in moderate to high yields, along with small amounts of 2-methylene-2,3-dihydro-1,4-thiazepines. The reaction was found to be general for a broad range of N-propargylic β-enaminothiones and tolerated the presence of aromatic, heteroaromatic and aliphatic groups with electron-withdrawing and electron-donating substituents. The method could be widened to the internal alkyne-tethered N-propargylic β-enaminothiones. This operationally simple method may provide rapid access to a library of functionalized pyridines of pharmacological interest.

Graphical abstract: A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones

Back to tab navigation

Supplementary files

Article information


Submitted
22 Dec 2018
Accepted
07 Feb 2019
First published
07 Feb 2019

Org. Biomol. Chem., 2019,17, 2529-2541
Article type
Paper

A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones

Y. Kelgokmen and M. Zora, Org. Biomol. Chem., 2019, 17, 2529
DOI: 10.1039/C8OB03180K

Social activity

Search articles by author

Spotlight

Advertisements