113261-11-3Relevant academic research and scientific papers
Improved Synthetic Method for 5-[(Phenylthio)methyl]oxazoline Derivatives: Electrophilic Cyclization of Allylic Amide Using a Bronsted Acid and Tetrabutylammonium Chloride under Mild Conditions
Nagao, Yoshihiro,Hiroya, Kou
, p. 813 - 817 (2020)
The synthesis of oxazolines using electrophilic cyclization of allylic amide is a simple and powerful method. However, cyclization involving arylsulfenylation requires harsh reaction conditions. We found that the reaction proceeds under mild heating conditions with the combination of a Bronsted acid and tetrabutylammonium chloride. This method enabled the synthesis of 5-[(arylsulfenyl)methyl]oxazoline derivatives under mild conditions and demonstrated high tolerance for various functional groups.
New Routes to Heterocycles via Sulphenylation of Unsaturated Amides
Samii, Zakaria K. M. Abd El,Ashmawy, Mohamed I. Al,Mellor, John M.
, p. 2517 - 2522 (2007/10/02)
The reaction of manganese(III) acetate with diphenyl disulphide in dichloromethane-trifluoroacetic acid in the presence of N-allylacetamide, followed by hydrolysis, affords a vicinal hydroxy sulphide.Similarly, addition to N-allyltrifluoroacetamide affords hydroxy sulphide adducts, but with different regioselectivity.N-Allylbenzamide and other unsaturated benzamides under similar conditions give cyclic products, 4,5-dihydro-1,3-oxazoles.Homoallylic amides give 5,6-dihydro-4H-1,3-oxazines.Amides derived from pent-4-enylamine give substituted pyrrolidines by cyclisation through nitrogen, but N-hex-5-enylbenzamide gives only an acyclic adduct.Unsaturated carboxylic acids and unsaturated carboxamides are transformed in good yield into lactones under similar conditions.
NEW ROUTES TO HETEROCYCLES VIA SULPHENYLATION OF UNSATURATED AMIDES
Samii, Zakaria K M Abd El,Ashmawy, Mohamed I Al,Mellor, John M
, p. 1949 - 1952 (2007/10/02)
Reaction of manganic acetate with organic disulphides in dichloromethane trifluoroacetic acid in the presence of a variety of unsaturated amides leads to intramolecular cyclisation with formation of sulphenylated oxazolines, oxazines or tetrahydropyrroles.
