113261-17-9Relevant academic research and scientific papers
5-Exo versus 6-Endo cyclization of primary aminyl radicals: An experimental and theoretical investigation
Liu, Feng,Liu, Kun,Yuan, Xinting,Li, Chaozhong
, p. 10231 - 10234 (2008/09/17)
(Chemical Equation Presented) The cyclization of neutral primary pent-4-enylaminyl radicals was investigated experimentally and theoretically. Unlike the corresponding secondary aminyl radicals, primary pent-4-enylaminyl radicals underwent efficient cyclization to afford the pyrrolidine and/or piperidine products in good to high yields. While the simple pent-4-enylaminyl radical gave predominately the 5-exo cyclization product, 4-chloropent-4- enylaminyl radicals led to the formation of the corresponding 6-endo cyclization products in excellent regioselectivity. Theoretical calculations revealed that the 5-exo cyclization rate of primary aminyl radicals is about 3-4 orders of magnitude higher than that of secondary aminyl radicals.
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.
