Functionalization of Primary C–H Bonds in Picolines toward Pyridylthioamides

We report a method for coupling of nitroarenes, 2- or 4-methylazaarenes, and elemental sulfur to afford (2-pyridyl)aryl thioamides. Good tolerance of functionalities was observed, including primary and secondary amines, bromo, iodo, ester, and boronic ester groups. Thioamides derived from pyrazole,...

Full description

Saved in:
Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2020-06, Vol.93 (6), p.783-789
Main Authors: Ho, Tuan H, Le, Ha H K, To, Tuong A, Nguyen, Tung T, Phan, Nam T S
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Heterocyclic compounds
Pyrazole
Quinoline
Quinoxalines
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We report a method for coupling of nitroarenes, 2- or 4-methylazaarenes, and elemental sulfur to afford (2-pyridyl)aryl thioamides. Good tolerance of functionalities was observed, including primary and secondary amines, bromo, iodo, ester, and boronic ester groups. Thioamides derived from pyrazole, thiazole, quinoline, quinoxalines, and azoles were obtained in good yields, showing the compatibility of heterocycles. This appears to be a general method to obtain pyridyl thioamides in one step from commercial, simple substrates.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20200004