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,...

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Published inBulletin of the Chemical Society of Japan Vol. 93; no. 6; pp. 783 - 789
Main Authors Ho, Tuan H, Le, Ha H K, To, Tuong A, Nguyen, Tung T, Phan, Nam T S
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 15.06.2020
Chemical Soc Japan
Chemical Society of Japan
Subjects
Amines
Antifungal agents
Aromatic compounds
Chemistry
Chemistry, Multidisciplinary
Heterocyclic compounds
Physical Sciences
Pyrazole
Quinoline
Quinoxalines
Science & Technology
Substrates
Elemental sulfur
Pyridylthioamide
Picolines
TRISULFUR RADICAL-ANION
ACIDS
DERIVATIVES
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ISSN0009-2673
1348-0634
DOI10.1246/bcsj.20200004

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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.
Bibliography:ObjectType-Article-1
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ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20200004