2832-99-7Relevant academic research and scientific papers
A new versatile one-pot synthesis of functionalized thioamides from Grignards, carbon disulfide and amines
Katritzky,Moutou,Yang
, p. 1497 - 1505 (2007/10/02)
The one-pot successive reactions of Grignard reagents with carbon disulfide and amines mediated by 1-trifluoromethylsulfonylbenzotriazole or triflic anhydride, provide an attractive and general route to thioamides. A wide variety of amines (primary alkyl, arylalkyl, secondary alkyl, cyclic amines, aniline, N-substituted anilines, heterocyclic amidines, amino alcohols, amino ethers, amino acetals, amino ketones, amino esters, amino amides (peptides), aminoalkenes, and diamines) and Grignards (primary alkyl, arylalkyl, aryl, secondary alkyl and tertiary alkyl) can be used, and thioamides are generally formed in good to moderate yields.
The reaction of α-amino-substituted diphenylphosphine oxide anions with elemental sulfur and selenium. A new route to thio- and selenoamides
Otten, P. A.,Gen, A. van der
, p. 499 - 506 (2007/10/02)
The lithiated anions of α-amino-substituted diphenylphosphine oxides 1, in which R can be hydrogen, aryl, alkyl and alkenyl, react with two equivalents of sulfur or selenium to form thio- and selenoamides, which can be isolated in good to excellent yields
Macrocyclic Lactone Formation through Sulfide Contraction. Synthesis of (+/-)-Diplodialide A
Ireland, Robert E.,Brown, Frank R.
, p. 1868 - 1880 (2007/10/02)
A methodology for the synthesis of macrocyclic β-keto-lactones from ω-hydroxy thioamides is described.The hydroxy thioamides were esterified with chloroacetyl chloride, and the resulting chloro esters underwent Eschenmoser sulfide contraction when treated with sodium iodide, diisopropylethylamine, and triethyl phosphite in acetonitrile.The β-keto lactones were obtained in 25-58 percent yield.The utility of the method was demonstrated by synthesis of diplodialide A.
