The catalytic role of elemental sulfur in the DMSO-promoted oxidative coupling of methylhetarenes with amines: synthesis of thioamides and bis-aza-heterocycles

Thioamides could be conveniently synthesized in good to excellent yields via DMSO-promoted oxidative coupling of methylhetarenes with amines in the presence of a near stoichiometric amount of sulfur (1.25 equiv.). Both aliphatic and aromatic amines were found to be competent substrates. When aniline...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-04, Vol.8 (7), p.1593-1598
Main Authors: Thi Thu Tram Nguyen, Nguyen, Le Anh, Ngo, Quoc Anh, Koleski, Marina, Nguyen, Thanh Binh
Format: Article
Language:English
Subjects:
Amines
Aniline
Catalysis
Chemical Sciences
Coupling
Organic chemistry
Substrates
Sulfur
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Summary:Thioamides could be conveniently synthesized in good to excellent yields via DMSO-promoted oxidative coupling of methylhetarenes with amines in the presence of a near stoichiometric amount of sulfur (1.25 equiv.). Both aliphatic and aromatic amines were found to be competent substrates. When anilines o-substituted by cyclizable groups such as OH, NH2, NHPh, SH and CONH2 were used as amine substrates, the corresponding hybrid bis-aza-heterocycles were formed in high yields even with a sulfur loading as low as 0.5 equiv.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo01654c