Thoination of N-alkyl-O-acyl hydroxamic acid derivatives via Lawesson's reagent

• Published in: Journal of molecular structure Vol. 1249; p. 131497
• Main Author: Al-Faiyz, Yasair S.S.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.02.2022
• Subjects: [3,3]-sigmatropic rearrangement; Hydroxamic acids; Lawesson's reagent; Thiohydroxamic acids; Thoination; Hydroxamic acids; Thoination; [3,3]-sigmatropic rearrangement; Thiohydroxamic acids; Lawesson's reagent
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.131497

•N-alkyl-O-acyl thiohydroxamic acid derivatives were prepared in good yields by the treatment of their parent hydroxamic acids with Lawesson's reagent.•This thionation process is more likely to be Witting-reaction-like involves four-membered ring intermeiate.•Some of these thiohydroxamic acid derivatives exhibit the ability to undergo rearrangement under basic conditions possibly via [3,3]-sigmatropic in moderate to good yields. N-alkyl-O-acyl thiohydroxamic acid derivatives were prepared in good yields by the treatment of their parent hydroxamic acids with Lawesson's reagent. Some of these thiohydroxamic acid derivatives exhibit the ability to undergo rearrangement under basic conditions possibly via [3,3]-sigmatropic in moderate to good yields similar to their parent hydroxamic acids. [Display omitted]